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Glycosphingolipid

(total 581)
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No Structure COMMON NAME NAME DATA No INFORMANT SYMBOL FORMULA MOL.WT(ave) Download BIOOGICAL ACTIVITY PHYSICAL AND CHEMICAL PROPERTIES SPECTRAL DATA CHROMATOGRAM DATA SOURCE CHEMICAL SYNTHESIS METABOLISM GENETIC INFORMATION NOTE REFERENCES
MELTING POINT BOILING POINT DENSITY REFRACTIVE INDEX OPTICAL ROTATION SOLUBILITY UV SPECTRA IR SPECTRA NMR SPECTRA MASS SPECTRA OTHER SPECTRA
1
Galactosyl sulfatide
Galactosylceramide 3-sulfate
GSG0069
Ineo Ishizuka
SM4s, SGC
Download ChemDraw structure file
Review (Ref. 0208). Inhibition of the arylsulfatase A activity (Ref. 0003/0006/0010/0011/0012/0013/0016/0047/0048/0054). Myelin components (Ref. 0016/0023). Interaction with GM2 activator protein (Ref. 0238). Stimulation of the evolution of oxygen radicals in polymorphonuclear leukocytes (Ref. 0024). Cannot be hydrolyzed by glucosulfatase (Ref. 0015). Mouse monoclonal antibodies (Ref. 0043/0050). Regulation of sulfotransferase activity (Ref. 0240).
Behavior in the Folch partition (Ref. 0027). Precipitates from hot methanol (Ref. 0004).
820cm-1 (Ref. 0001/0029/0031).
H-C COSY spectrum of sulfatide (Ref. 1498)
[Spectrum 0001](I.Ishizuka)
DQF COSY spectrum of sulfatide
[Spectrum 0002](I.Ishizuka)
EI-MS (Ref. 0033), SI-MS (Ref. 0036).TLC-blotting/negative-ion LSIMS of galactosyl sulfatide
[Spectrum 0003](I.Ishizuka)
Absorption of the complex with Azure A the abssorption of the acetates of sulfoglycolipids with Azure A (Ref. 0027).

2D TLC of male
[Chromatogram 0001]and female
[Chromatogram 0002] wild type and CGK-KO mice(I.Ishizuka).
DEAE Sephadex column chromatography of female wild type and CGK-KO mice
[Chromatogram 0003](I.Ishizuka).
Review (Ref. 0208). Bull frog and axolotl (Ref. 0237); Human brain (Ref. 0002/0001); the white and gray matter of the human brain (Ref. 0009); rabbit brain, white matter (Ref. 0057). Rat brain (Ref. 0017/0020), effect of chronic treatment with diazepam (Ref. 0055), regional distribution (Ref. 0020). Human kidney (aged, 0.39; middle age, 0.40; juvenile, 0.48mg/g dry tissue (Ref. 0004). Porcine pancreas (Ref. 0031), rabbit stomach (antrum, pylorus), duodenum jejunum (Ref. 0053). Brain (review) (Ref. 0016). C6 glioma derived from rat brain (Ref. 0032), cod brain (Ref. 0021). Mouse (C57BL) kidney (Ref. 0230), brain, liver, kidney (Ref. 0231).



The fatty acid composition, human kidney:22:0, 23:0, 24:0, 24:1, h24:0, h23:0, h24:1 (Ref. 0004)
2
Lactosylsulfatide
HSO3-3Galb1-4GlcCer
GSG0070
Ineo Ishizuka
SM3
Download ChemDraw structure file
Inhibition of the arylsulfatase A activity (Ref. 0010/0048). Interaction with laminin, thrombospondin, and von willebrand factor (Ref. 0044/0056). Interaction with Sulph I monoclonal antibody (Ref. 0050).
Behavior in the Folch partition (Ref. 0027).
Similar to galactosylsulfatide except for smaller 1240cm-1 (Ref. 0004).

EI-MS (permethylated)
[Spectrum 0001] (Ref. 0033), SI-MS
[Spectrum 0002](Ref. 0036).TLC-blotting/negative-ion LSIMS of mouse lactosyl sulfatide (SM3)
[Spectrum 0003](I.Ishizuka)
Absorption of the complex with Azure A, the abssorption of the acetates of sulfoglycolipids with Azure A (Ref. 0027).

Review (Ref. 0208). Human kidney (Ref. 0004/1244) Faged, 0.14mg/g, middle age, 0.18mg/g juvenile, 0.20mg/g dry weight. Human kidney (Ref. 0010) cultured kidney epithelial cell lines MDCK (Ref. 0046/0019) JTC-12 (Ref. 0019) MDBK, LLC-PK1 (Ref. 0025). Trout (salmon?) testis (Ref. 0014), suncus kidney (Ref. 0034) rat kidney (Ref. 0026) dolphin kidney (Ref. 0039). Canine small intestine(Ref. 1245). Porcine gastric mucosa(Ref. 1246)



Human kidney, the major fatty acids, 22:0, 24:0, 24:1, 24h:0, 24h:1 (Ref. 0004)
3
Gangliotriaosylceramide sulfate
Gangliotriaosylceramide sulfate
GSG0071
Ineo Ishizuka
SM2a
Download ChemDraw structure file
Interaction with laminin, thrombospondin, and von willebrand factor (Ref. 0044/0056/0078).
Behavior in the Folch partition (Ref. 0027).
OH, 3600-3100cm-1; sulfate (eq), 1230 and 815cm-1 (Ref. 0076).
1H-NMR in C/M, 2:1 at 55degC; 4.81 ppm (3J/1,2 = 8.0), GalNAc; 4.50 ppm (3J/1,2 = 7.4), Gal; 1H-NMR in DMSO, 25degC; 4.46 ppm (J = 7.9), GalNAc; 4.30 (J = 7.4), Gal; 4.20 (J = 7.7), Glc (Ref. 0026).
EI-MS (permethylated) (Ref. 0033), SI-MS (Ref. 0036). Negative-mode LSIMS and CID (Ref. 0214).
Absorption of the complex with Azure A,the abssorption of the acetates of sulfoglycolipids with Azure A (Ref. 0027).

Review (Ref. 0208). Rat kidney (Ref. 0076/0026) A kidney epithelial cell line JTC-12 (Ref. 0025/0077).




The long-chain base is predominantly t18:0 (Ref. 0208)
4
bis-sulfo-Gangliotriaosylceramide
bis-sulfo-Gangliotriaosylceramide
GSG0072
Ineo Ishizuka
SB2
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Interaction with laminin, thrombospondin, and von willebrand factor (Ref. 0044).
Behavior in the Folch partition (Ref. 0027).
The sulfate ester, 1240,820cm-1 (Ref. 0079).
1H-NMR (Ref. 0080).
EI-MS (trideuteriomethylated after permethylation-soluvolysis) (Ref. 0080); Hex, m/z 219+3; Hex-CD3OH, m/z 187 (Ref. 0080/0033), SI-MS (Ref. 0036). Negative-mode LSIMS and CID (Ref. 0214).
Absorption of the complex with Azure A,the abssorption of the acetates of sulfoglycolipids with Azure A (Ref. 0027).

Review (Ref. 0208). Rat kidney (Ref. 0079/0080).




The long-chain base is predominantly t18:0 (Ref. 0208)
5
Sulfogangliotetraosylceramide
Sulfogangliotetraosylceramide
GSG0073
Ineo Ishizuka
SM1a
Download ChemDraw structure file

Behavior in the Folch partition (Ref. 0027).

EI-MS (permethylated) (Ref. 0033). Negative-mode LSIMS and CID (Ref. 0214).
Absorption of the complex with Azure A, the abssorption of the acetates of sulfoglycolipids with Azure A (Ref. 0027).

Review (Ref. 0208).




The long-chain base is predominantly t18:0 (Ref. 0208)
6
Sulfogangliotetraosylceramide
Sulfogangliotetraosylceramide
GSG0074
Ineo Ishizuka
SM1b
Download ChemDraw structure file
Interaction with laminin (Ref. 0044).
1H-NMR (Ref. 0082).
FAB-MS (Ref. 0082).Negative-ion LSIMS and CID of gangliotetraosylceramide sulfate (SM1b)
[Spectrum 0001](I.Ishizuka)


Review (Ref. 0208). Mouse intestine (Ref. 0044).




The long-chain base is predominantly t18:0 (Ref. 0208)
7
Bis-sulfo-gangliotetraosylceramide
Bis-sulfo-gangliotetraosylceramide
GSG0075
Ineo Ishizuka
SB1a
Download ChemDraw structure file
Interaction with laminin, thrombospondin, and von willebrand factor (Ref. 0044). Interaction with monoclonal antibodies 2H6G5 (IgM) and 4A9E10 (IgG3) (Ref. 0083).
Behavior in the Folch partition (Ref. 0027).
1H-NMR in C/M 1:1 at 55degC: 4.46 ppm (J = 7.8 Hz), Gal (two doublets); 4.74 ppm (J = 7.4 Hz), GalNAc; in DMSO, 60degC: 4.51 ppm (J = 8.0), GalNAc; 4.32 ppm (J = 8.1), the terminal Gal; 4.33 ppm (J = 7.8), the internal Gal (Ref. 0081).
EI-MS (permethylated): m/z 222, 3-deuteriomethylated-2,4,6-trimethyl-Gal; m/z 187, 222-CD3OH (Ref. 0081/0033) SI-MS (Ref. 0036).
Negative-mode LSIMS and CID (Ref. 0214).TLC-blotting/negative-ion LSIMS of mouse kidney SB1a
[Spectrum 0001](I.Ishizuka)
Absorption of the complex with Azure A,the abssorption of the acetates of sulfoglycolipids with Azure A (Ref. 0027).

Review (Ref. 0208). Rat kidney (Ref. 0081) human hepatoma PLC/PRF/5 (Ref. 0083).




The long-chain base is predominantly t18:0 (Ref. 0208)
8
Sulfoglobotetraosylceramide
Sulfoglobotetraosylceramide
GSG0076
Ineo Ishizuka
SMGb4Cer
Download ChemDraw structure file
Interaction with thrombospondin (Ref. 0056).
1240, 810cm-1: sulfate (Ref. 0056).
1H-NMR (anomeric protons) (Ref. 0056).
Negative SI-MS (Ref. 0056).


Review (Ref. 0208). Human kidnedy (Ref. 0056). Rat kidney, 0.07 nmol/g tissue (Ref. 0212).



Fatty acids 24:0, 48%; 22:0, 16% (Ref. 0056)

LCB t18:0, 100%
9
Globopentaosylceramide sulfate
Globopentaosylceramide sulfate
GSG0077
Ineo Ishizuka
SMGb5Cer
Download ChemDraw structure file
Interaction with thrombospondin (Ref. 0084).
1240 cm-1: SO stretching, 810cm-1: C-O-S vibration (Ref. 0084).
1H-NMR: H-1-H-4 double-relayed COSY (Ref. 0084).
Negative SI-MS (Ref. 0084).


Review (Ref. 0208). Human kidney (Ref. 0084).



Fatty acids 24:0, 27%; 22:0, 24%; 16:0, 19% (Ref. 0084).
10
SMUnLc4Cer
GSG0078
Ineo Ishizuka
SGGL, SMUnLc4Cer
Download ChemDraw structure file
An adhesion molesule of neurons (Ref. 0223).

FAB-MS: Pertrimethylsilylated desulfated or permethylated desulfated derivative (Ref. 0085).


Review (Ref. 0208/0223). Human peripheral nerve (Ref. 0085).



Fatty acids 16:0, 13%; 18:1, 16%; 18:0, 11%; 24:1, 13%; 24:0, 15% (Ref. 0085).
11
HNK-1 antigen glycolipid
HNK-1 antigen glycolipid
GSG0079
Ineo Ishizuka
SGGL, SMUnLc6Cer
Download ChemDraw structure file





Review (Ref. 0208/0223). Human peripheral nerve (Ref. 0085).


Expression cloning of the sulfotransferase (Ref. 0241).

12
Galactosylceramide 6-sulfate
GSG0080
Ineo Ishizuka
SM4s-6
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Interaction with laminin, thrombospondin, and von willebrand factor (Ref. 0044/0208).
165-170 (Ref. 0088).
[a]/589 = -0.4 (2.4% in pyridine) (Ref. 0088).
Sparingly soluble in acetone (Ref. 0088).
Identical with galactosylceramide 3-sulfate (Ref. 0088).




Chemical synthesis (Ref. 0088). Review (Ref. 0208).




13
8-Sulfo-N-glycolylneuraminyl-(a2-6)-glucosyl-(1-8)-N-glycolylneuraminyl-(a2-6)-glucosyl-(1-1)-ceramide
GSG0081
Ineo Ishizuka
Download ChemDraw structure file
Protects embryonic cells from toxic amines (Ref. 0089).
1220cm-1: S=O stretching, 800cm-1: C-O-S vibration (Ref. 0089).

As TMS derivative of methylated-reduced glycolipid (Ref. 0089).


Sea urchin (Strongylocentrotus intermedius) egg and embryo (Ref. 0089). Review (Ref. 0208).



Hydroxy and nonhydroxy fatty acids (Ref. 0089)

Long-chain base, t18:0 (Ref. 0089)
14
8-Sulfo-N-glycolylneuraminosyl-(a2-6)-b-D-glucopyranosyl-(1-1)-ceramide
GSG0082
Ineo Ishizuka
Download ChemDraw structure file

1283cm-1: S-O vibration, 810cm-1: S-O bond (Ref. 0090).

Permethylated asialo-derivative (Ref. 0090).Negative-ion LSIMS and high-energy CID of GM1a sulfate
[Spectrum 0001](I.Ishizuka)

DEAE Sephadex column chromatography of GM1a sulfate
[Chromatogram 0001]
Sea urchin Echinocardium cordatum, gonads (Ref. 0090). Review (Ref. 0208).



Fatty acids, 15:0, 24h:0, 22h:0, 22h:1, 18h:0, 23h:0 (Ref. 0090)

LCB, t18:0, t16:0, t17:0 (Ref. 0090)
15
Lysosulfatide
3-Sulfogalactosyl-b-(1-1)-sphingosine
GSG0083
Ineo Ishizuka
Download ChemDraw structure file

C
MALDI-TOFMS
[Spectrum 0001] (T.Taketomi) (Ref. 3072)(Ref. 0097).


Sulfation of psychosine by rat stomach mucosa (Ref. 0022). Review (Ref. 0208).




16
Glucosylsulfatide
Glucosylceramide 3-sulfate
GSG0084
Ineo Ishizuka
SM4s-Glc
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1230cm-1: S=O stretching, 815cm-1: C-O-S vibration (Ref. 0093).
1H-NMR: double-relayed COSY (Ref. 0093).
SI-MS [M-H]- (Ref. 0093).


Review (Ref. 0208). Rat kidney (Ref. 0093).




17
Sulfo-isoglobotetraosylceramide
Sulfo-isoglobotetraosylceramide
GSG0092
Ineo Ishizuka
SMiGb4Cer
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Sulfate (Ref. 0212).
DQF-COSY (Ref. 0212).
LSIMS (Ref. 0212).

Silica beads (Ref. 0212).
Review (Ref. 0208). Rat kidney, 0.27 nmol/g tissue (Ref. 0212).



Fatty acids 24:0, 37%; 22:0, 19%; 23:0, 15% (Ref. 0212).
18
Sulfo-isoglobopentaosylceramide
Sulfo-isoglobopentaosylceramide
GSG0093
Ineo Ishizuka
Download ChemDraw structure file

FT-IR, sulfate ester (Ref. 1062).
1H-NMR, DQF-COSY (Ref. 1062).
LSIMS, CID (Ref. 0212).


Rat kidney, 0.11 nmol/g tissue (Ref. 1062). Review (Ref. 0208).



Fatty acids 24:0, 23%; 22:0, 22% (Ref. 1062)

LCB t18:0, 89%
19
Gangliotriaosylceramide sulfate
Gangliotriaosylceramide sulfate
GSG0094
Ineo Ishizuka
SM2b
Download ChemDraw structure file

FT-IR (Ref. 0215).
1H-NMR, DQF-COSY (Ref. 0215).
Negative-mode LSIMS, CID (Ref. 0215).


Rat kidney, 50 pmol/g tissue (Ref. 0215). Review (Ref. 0208).



Fatty acids 24:0, 31%; 22:0, 22%; 23:0, 12%; LCB t18:0, 76% (Ref. 0215).
20
Sulfated GM1a ganglioside
Sulfated GM1a ganglioside
GSG0095
Ineo Ishizuka
SMGM1a
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FT-IR (Ref. 0217).
1H-NMR, DQF-COSY (Ref. 0217).
Negative LSIMS and CID (Ref. 0217).


Rat kidney, 120 pmol/g tissue (Ref. 0217). Review (Ref. 0208).



Fatty acids 24:0, 34%; 22:0, 20%; LCB t18:0, 96% (Ref. 0217).
21
6-O-acyl sulfatide
6-O-acylgalactosylceramide 3-sulfate
GSG0113
Ineo Ishizuka
Download ChemDraw structure file

1H-NMR (Ref. 0243).
FAB-MS (Ref. 0243).

DEAE Sephadex (Ref. 0243).
Equine brain (Ref. 0243).



The fatty acid composition of the O-acyl group, 18:0, 16:0 (Ref. 0243)
22
GalNAcb1-4(Ac-O-9-NeuAc2-8NeuAc2-8NeuAc2-3)Galb1-4GlcCer
GSG1001
Kazuo Nakamura
Download ChemDraw structure file


FAB-MS (Ref. 0030)

Alaskan pollack brain (Ref. 1030)




23
NeuAc2-3Galpb1-3(Fuca1-4)GlcpNAcb1-3(Galpb1-4GlcpNAcb1-6)Galpb1-4GlcCer
GSG1002
Kazuo Nakamura
Download ChemDraw structure file

1H-NMR (Ref. 1031)



Human rectal adenocarcinoma (Ref. 1031)




24
NeuAc2-3Galb1-3(Fuca1-4)GlcNAcb1-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcCer
GSG1003
Kazuo Nakamura
sLea-X
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1H-NMR (Ref. 1031)



Human rectal adenocarcinoma (Ref. 1031)




25
NeuAc2-3Galb1-3(Fuca1-4)GlcNAcb1-3{Galb1-4(Fuca1-3)GlcNAcb1-6}galb1-4GlcCer
GSG1004
Kazuo Nakamura
Download ChemDraw structure file

1H-NMR (Ref. 1031)



Human rectal adenocarcinoma (Ref. 1031)




26
NeuAc2-3Galb1-3(NeuAc2-6)GalNAcb1-3Gala1-4Galb1-4GlcCer
GSG1005
Kazuo Nakamura
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1H-NMR 500MHz (Ref. 1032)
Negative FAB-MS (Ref. 1032)

Mobility on TLC with C/M/W(50:40:10): between GD1a and GD1b (Ref. 1032)
Human erythrocyte, Chicken skeletal muscle (Ref. 1032), starfish, Asterina pectinifera. II. (Ref. 1248)



Ceramides Human erythrocyte: 24:0-d18:1 and 22:0-d18:1 ; chicken keletal muscle 18:0-d18:1 (Ref. 1032)
27
NeuGc2-3Galb1-4GlcNAcb1-3(Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1006
Kazuo Nakamura
Download ChemDraw structure file

1-d 1H-NMR (Ref. 1034)
FAB-MS (Ref. 1034)

Mobility on TLC with C/M/W (55:45:10), slightly lower than GD1b; with C/M/1.5N ammmonia (55:45:10), lower than GQ1b; with tetrahydrofuran/0.1%KCl (75:15) between GT1b and GQ1b (Ref. 1034)
Bovine erythrocytes (Ref. 1034)



Fatty acids 18:1(22.3%), 22:1(13.5%), 18:0(11.1%), C16:0(10.8%) (Ref. 1034)

LCB d18:0(5%), d18:1(95% ) (Ref. 1034)
28
NeuAc2-6Galb1-4GlcNAcb1-3(Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1007
Kazuo Nakamura
Download ChemDraw structure file

500MHz 1-d 1H NMR (Ref. 1035)
Negative FAB-MS (Ref. 1035)

Mobility on TLC with C/M/0.2%CaCl2 (60:40:9), slightly higher than blood group I-active ganglioside (Ref. 1035)
Human meconium (Ref. 1035)



Ceramides 16h:0-d18:1, 22h:0-d18:1, 24h:0-d18:1 (Ref. 1035)
29
NeuAc2-3Galb1-3(NeuAc2-6)GalNAcb1-4(NeuAc2-8NeuAc2-3)Galb1-4GlcCer
GSG1008
Kazuo Nakamura
Download ChemDraw structure file
Reactive with anti-cholinergic neuron specific antibody (Ref. 1036)
600MHz 1-d 1H (Ref. 1036)
Negative FAB-MS (Ref. 1036)

Mobility on TLC with C/M/12mM MgCl2 (5:4:1), C/M/12mM MgCl2/15M NH4OH(5:4:0.7:0.3), lower than GQ1b (Ref. 1036)
Bovine brain (Ref. 1036)



Fatty acids 16:0 (1.2%), 18:0 (91.3%), 20:0(4.4%), 22:0 (3% ) (Ref. 1036)
30
NeuGc2-3Galb1-4GlcNAcb1-3Galb1-3GalNAcb1-4(NeuGc2-3)Galb1-4GlcCer
GSG1009
Kazuo Nakamura
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1d 1H, 2d HOHAHA (Ref. 1037)
Negative FAB-MS (Ref. 1037)

Mobility on TLC with C/M/0.2%CaCl2 (60:40:9), between GD1b anad GT1b; withC/M/2.5N NH4OH (60:40:9), lower than GT1b.(Ref. 1037)
Rat spleen lymphosytes (Ref. 1037)



Fatty acids 18:0(4%), 20:0(9%), 21:0(2%), 22:0(14%), 23:0(5%), 24:1(44%), 24:0(22%) (Ref. 1037)

LCB d18:1 (Ref. 1037)
31
NeuAc2-?Galb1-?Galb1-?Gala1-?Galb1-?GlcCer
GSG1010
Kazuo Nakamura
Download ChemDraw structure file

500MHz 1-d 1H (Ref. 1038)


Mobility on TLC with C/M/0.2%CaCl2 (6:4:1) slightly higher than GD1a (Ref. 1038)
Mouse hematopoietic cell line BM216 (Ref. 1038)




32
GalNAcb1-4(NeuAc2-3)Galb1-3GlcNAcb1-3(GalNAcb1-4)Galb1-4GlcCer
GSG1011
Kazuo Nakamura
Download ChemDraw structure file
Reactive with serum IgM from an amyotrophic lateral aclerosis-like patient (Ref. 1039)
400MHz 1-d 1H (Ref. 1039)
Negative FAB-MS (Ref. 1039)

Mobility on TLC with C/M/12mM MgCl2(5:4:1), slightly higher than GD1a; with C/M/12mM MgCl2/2.5M ammonia(50:40:7:3), slightly higher than GD1b (Ref. 1039)
Bovine brain (Ref. 1039)



Ceramides C18:0-d18:1 or C18:0-d20:1 (Ref. 1039)
33
GalNAcb1-4(NeuAca2-3)Galb1-3GlcNAcb1-3(Galb1-3GalNAcb1-4)Galb1-4GlcCer
GSG1012
Kazuo Nakamura
Download ChemDraw structure file
Reactive with serum IgM from an amyotrophic lateral aclerosis-like patient (Ref. 1039)
400MHz 1-d 1H (Ref. 1039)
Negative FAB-MS (Ref. 1039)

Mobility on TLC with C/M/12mM MgCl2(5:4:1), between GD1a and GD1b; with C/M/12mM MgCl2/2.5M ammonia (50:40:7:3), higher than GQ1b (Ref. 1039)
Bovine brain (Ref. 1039)



Ceramides C18:0-d18:1 or C18:0-d20:1 (detected with FAB-MS) (Ref. 1039)
34
Galb1-6Galb1-6GlcCer
GSG1013
Kazuo Nakamura
Download ChemDraw structure file

500MHz 1H-NMR
[Spectrum 0001] (Ref. 0040)
NEGATIVE FAB-MS
[Spectrum 0002] (Ref. 0040)

TLC, lower than CTH with C/M/W(65:25:4)
[Chromatogram 0001] (Ref. 1040)
Eggs of Hemicentrotus pulcherrimus (sea urchin) (Ref. 1040)



Fatty acids 22:1(61.4%), 22h:1(27.3%) (Ref. 1040)

LCB n-t18:0 (92.9%) (Ref. 1040)
35
Fuca1-3GalNAcb1-4(Fuca1-3)GlcNAcb1-4GlcCer
GSG1014
Kazuo Nakamura
Download ChemDraw structure file

2d-HOHAHA, DQF-COSY, 1d 1H 600MHz, NOESY (Ref. 1055)
NEGATIVE FAB-MS
[Spectrum 0001] (Ref. 1041)

Eggs of Hemicentrotus pulcherrimus (sea urchin) (Ref. 1041)



Fatty acids 22:1(47.1%), 22h:1(25.1%), 23:1(10.3%) (Ref. 1041)

LCB n-t18:0(89.7%) (Ref. 1041)
36
Galb1-6(Fuca1-3)Galb1-6GalCer
GSG1015
Kazuo Nakamura
Download ChemDraw structure file


LSI-MS (Ref. 1042)


Metacestodes of Echinococcus multilocularis (cestode) (Ref. 1042)



Fatty acids C16 and C18h, LCB d18:0 are major (Ref. 1042)
37
Fuca1-3Galb1-6GalCer
GSG1016
Kazuo Nakamura
Download ChemDraw structure file


LSI-MS (Ref. 1042)


Metacestodes of Echinococcus multilocularis (cestode) (Ref. 1042)



Fatty acids C16 and C18h, LCB d18:0 are major (Ref. 1042)
38
Galb1-3(Fuca1-4)GlcNAcb1-3Galb1-3(Fuca1-4)GlcNAcb1-3Galb1-4GlcCer
GSG1017
Kazuo Nakamura
Download ChemDraw structure file
Reactive with mAb NCC-ST-421 (raised against human gastric adenocarcinoma) (Ref. 1043)
1d 1H 500MHz (Ref. 1043)
Positive FAB-MS (Ref. 1043)


Human colonic Adenocarcinoma cell line Colo 205 (Ref. 1043)



Ceramides C24h:0-d18:1, C24h:1-d18:1, C24h:1-t18:0 (Ref. 1043)
39
KDNa2-3Galb1-4GlcCer
GSG1018
Kazuo Nakamura
(KDN)GM3
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1D 400MHz 1H
[Spectrum 0001], HOHAHA
[Spectrum 0002](Ref. 1044)
(-)FAB-MS
[Spectrum 0003](Ref. 1044)
1

Mobility on TLC with C/M/0.2% CaCl2(55:45:10), slightly lower than (NeuAc)GM3
[Chromatogram 0001](Ref. 1044)
Sperm of rainbow trout (Ref. 1044)



Fatty acids 16:0(95%), C24:1(5%) (Ref. 1044)

LCB d18:1 (Ref. 1044)
40
Galb1-3Gala1-4Galb1-4GlcCer
GSG1019
Kazuo Nakamura
Download ChemDraw structure file
One of the mAb (ST-3) specific for this glycosphingolipid inhibited macrophage invasion by amastigotes and promastigote (Ref. 1045)
500MHz 1d 1H (Ref. 1045)
Negative FAB-MS (Ref. 1045)


Amastigote form of Leishmania amazonensis (protozoan) (Ref. 1045)



Ceramides C16:0-d18:1 (Ref. 1045)
41
Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-3GalNAcb1-4(NeuAc2-3)Galb1-4GlcCer
GSG1020
Kazuo Nakamura
Download ChemDraw structure file
Antigen to mAb 188C1 (raised against skin tissue of bullfrogs). This antibody recognize a common antigen in neural and intestinal tissues of chicken. (Ref. 1046)
1d 1H (400MHz) (Ref. 1046)
Negative FAB-MS (Ref. 1046)

Mobility on TLC with C/M/14mM MgCl2(5:4:1), between GD1a and GD1b (Ref. 1046)
Chick intestinal tissues (Ref. 1046), Small intestine of guinea pig(Ref. 1202)



Fatty acids 16h:0( 24.9%), C22h:0 (31.3%); t18:0 (57.4%) (Ref. 1046)

LCB t18:0 (57.4%), d18:1 (19.1%) (Ref. 1046)
42
GalNAca1-3(Fuca1-2)Galb1-3GlcNAcb1-3Galb1-3GlcNAcb1-3Galb1-4GlcCer
GSG1021
Kazuo Nakamura
Ab
Download ChemDraw structure file
Blood group A active, Ab (Ref. 1047)
1d 1H (Ref. 1047)
EI-MS (Ref. 1047), TLC/(-)SIMS
[Spectrum 0001] (Ref. 1499), peracetylated sample TLC/(+)SIMS
[Spectrum 0002]

TLC (Ref. 1047)
Epithelial cells of the small intestine of inbred rats (DA and LOU/M) (Ref. 1047)



Ceramide, C16:h0-t18:0 (Ref. 1047)
43
NeuAc2-3Galb1-3GalNAcb1-4(NeuAc2-8NeuGc2-3)Galb1-4GlcCer
GSG1022
Kazuo Nakamura
Download ChemDraw structure file

1d 1H (Ref. 1048)
Negative FAB-MS (Ref. 1048)

Mobility on TLS with C/M/12mM MgCl2(5:4:1), slightly higher than GT1b; with C/M/12mM MgCl2/2.5M ammonia (50:40:7:3), between GT1b and GQ1b (Ref. 1048)
Bovine brain (Ref. 1048)



Ceramide C18:0-d20:0 (Ref. 1048)
44
1-O-b-D-{6-O-[2'-(Trimethylammonio)-ethylphosphoryl]}GalCer
GSG1023
Kazuo Nakamura
Download ChemDraw structure file

1H 400MHz (Ref. 1049)
FAB-MS (Ref. 1049)

TLC (Ref. 1049)
Neanthes diversicolor (marine annelid) (Ref. 1049)




45
Epidermoside(Ref. 1050)
Glucosylb-N-(w-O-linoleoyl)-acylsphingosine
GSG1024
Kazuo Nakamura
Download ChemDraw structure file
Suggested to be a barrier preventing the loss of water from the body surface <<>>
1H-HMR (360MHz) (Ref. 1483), 1H-HMR (500MHz)
[Spectrum 0002] (Ref. 1050),
Note, GL-I3:(omega-O-linoleoyl)-triacontanoyl and - and -dotriacontamonoenoyl-eicosashpingenine
GL-II3:(omega-O-linoleoyl)-triacontanoyl-tri-hydroxyeicosasphingenine
1H-HMR (400MHz)(Ref. 1485)
(-)FAB-MS
[Spectrum 0001] (Ref. 1050)
Note, GL-I3:(omega-O-linoleoyl)-triacontanoyl and - and -dotriacontamonoenoyl-eicosashpingenine
GL-II3:(omega-O-linoleoyl)-triacontanoyl-tri-hydroxyeicosasphingenine

pig epidermis (Ref. 1483), human epidermis (Ref. 1050), guinea pig epidermis (Ref. 1485), cultured human keratinocytes (Ref. 1484)



Ceramides Pig and human epidermis 30h:0-(w18:2)-d20:1, 32h:0-(w18:2)-d20:1 (Ref. 1050/1483), Human epidermis 30h:0-(w18:2)-t20:1(Ref. 1050) , Guinea pigs epidermis 24h:0-(w18:2) (Ref. 1485)
Cultured keratinocytes, w hydroxy acid; 30:0, 30:1, 32:1, 34:1 (Ref. 1484)

LCB Cultured keratinocytes, d18:1 (Ref. 1484)
46
3,4-O-Cyclic fatty acetal-GalCer
GSG1025
Kazuo Nakamura
Download ChemDraw structure file


FAB-MS (Ref. 1051)


Human brain (Ref. 1051)



Fatty acids C16:0,C18:1,C18:0,C24:1 (Ref. 1051)

LCB d18:1 (Ref. 1051)
47
4,6-O-Cyclic fatty acetal-GalCer
GSG1026
Kazuo Nakamura
Download ChemDraw structure file


FAB-MS (Ref. 1051)


Human brain (Ref. 1051)



Fatty acids C16:0,C18:1,C18:0,C24:1 (Ref. 1051)

LCB d18:1 (Ref. 1051)
48
Gala1-2Galb1-4(2-AEP1-6)GlcCer
GSG1027
Kazuo Nakamura
Download ChemDraw structure file


FAB-MS (Ref. 1052)


Aplysia juliana (sea hare) (Ref. 1052)



Fatty acids 16:0(61.9%), 18:0(24.2%) (Ref. 1052)

LCB d18:1(19.4%), branched d19:1(54.4%) (Ref. 1052)
49
(F-9)
[3,4-O-(S-1-Carboxyethylidene)]Galb1-3GalNAca1-3[6'-O-(2-aminoethylphosphonyl)Gala1-2](2-aminoethylphosphoryl-6)Galb1-4GlcCer
GSG1028
Kazuo Nakamura
Download ChemDraw structure file

1D 1H-NMR (400MHz)
[Spectrum 0001](Ref. 1053)

Aplysia kurodai (sea hare) (Ref. 1053)



Fatty acids 16:0(92%), 18:0(8%) (Ref. 1053)

LCB d18:1(37%), anteiso-d19:1(55%) (Ref. 1053)
50
(FGL-I)
[3,4-O-(S-1-Carboxyethylidene)]Galb1-3GalNAca1-3(Fuca1-2)(2-aminoethylphosphoryl1-6)Galb1-4GlcCer
GSG1029
Kazuo Nakamura
Download ChemDraw structure file

1D 1H-NMR (400MHz)
[Spectrum 0001](Ref. 1053)
(-)FAB-MS
[Spectrum 0002] (Ref. 1053)

Aplysia kurodai (sea hare) (Ref. 1053)



Fatty acids 16:0(94%), 17:0(3%), 18:0(3%) (Ref. 1053)

LLCB d18:1(39%), anteiso d19:1(48%) (Ref. 1053)
51
2-Aminoethylphosphoryl-6GlcNAcb1-3Manb1-4GlcCer
GSG1030
Kazuo Nakamura
Download ChemDraw structure file

(+)FAB-MS
[Spectrum 0003] (Ref. 1054)

Pupae of Calliphora vicina (Insecta: Diptera)(Ref. 1490)larvae of the green-bottle fly, Lucilia caesar(Ref. 2060)



Fatty acids 22:0(49.3%), 24:0(25.0%) (Ref. 1054)

LCB br-d18:1(54.7%), d18:1(24.5%), br-d19:1(20.8%) (Ref. 1054)
52
GalNAcb1-4(2aminoethylphosphoryl-6)GlcNAcb1-3Manb1-4GlcCer
GSG1031
Kazuo Nakamura
Download ChemDraw structure file

1H NMR (SP0001) (Ref. 1054)
(+)FAB-MS
[Spectrum 0002] (Ref. 1054)

TLC : lane 3
[Chromatogram 0001] (Ref. 1054)
Pupae of Calliphora vicina (Insecta: Diptera)(Ref. 1490)larvae of the green-bottle fly, Lucilia caesar(Ref. 2060)



Fatty acids 22:0(56.0%), 24:0(20.9%) (Ref. 1054)

LCB br-d18:1(52.5%), d18:1(18.7%), br-19:1(28.8%) (Ref. 1054)
53
Galb1-3GalNAcb1-4(NeuNa2-3)Galb1-4GlcCer
GSG1032
Kazuo Nakamura
De-N-Acetylated GM1
Download ChemDraw structure file
Reactive with cholera toxin B-subunit (Ref. 1056)
1-d1H (Ref. 1056)
FAB-MS (Ref. 1056)


Bovine brain (Ref. 1056)




54
Manb1-4(Fuca1-3)GlcCer
GSG1033
Kazuo Nakamura
Download ChemDraw structure file

400MHz 1H-NMR : b-GLUCOSE : 4.21ppm(J1,2=7.9Hz), b-MANNOSE : 4.65ppm, a-FUCOSE : 5.26ppm(J1,2=3.6Hz), FUCOSE H-5 : 4.30ppm (Ref. 1057)
(-)FAB-MS : [M-H]-=1104,1090,1076, [M-Fuc-H)-=958,944,930, [M-Man-H]-=942, 928,914, [M-Fuc-Man-H]-=796,782,768, CERAMIDE=634,620,606 (Ref. 1057)


Parafontaria laminata armigera (millipede)(Ref. 1057)



Fatty acids normal 27.9% (16:0,22:0,23:0,24:0), 2-hydroxy 32.6% (22:0,23:0,24:0), 3-hydroxy 39.5% (22:0,23:0,24:0)

LCB branched d17:1 8.6%, d17:1 28.4%, d17:0 15.3% , branched d18:1 23.5%, d18:1 24.2% (Ref. 1057)
55
Cholinephosphoryl-6(Mana1-4)Gal1-6GalCer
GSG1034
Kazuo Nakamura
Download ChemDraw structure file

3400cm-1, 1620cm-1, 1540cm-1, 1220cm-1, 960cm-1 (Ref. 1058)
500MHz 1H (Ref. 1058)
(+)FAB-MS (Ref. 1058)


Pheretima hilgendorfi (earthworm) (Ref. 1058)



Fatty acids 24:0(21.8%), 23:0(11.2%), 22:0(51.7%) (Ref. 1058)

LCB br-d18:1(53.4%), d18:1(20.0%), br-d19:1 (26.4%) (Ref. 1058)
56
GalNAca1-4GalNAcb1-4(2aminoethylphosphoryl-6)GlcNAcb1-3Manb1-4GlcCer
GSG1035
Kazuo Nakamura
Download ChemDraw structure file

3400cm-1, 1620cm-1, 1540cm-1, 1220cm-1, 960cm-1(Ref. 1058)
500MHz 1H (Ref. 1058)
(+)FAB-MS (Ref. 1058)


Pupae of Calliphora vicina (Insecta: Diptera)(Ref. 1490)larvae of the green-bottle fly, Lucilia caesar(Ref. 2060)



Fatty acids 22:0(50.8%), 23:0(11.9%), 24:0(21.7%) (Ref. 1058)

LCB br-d18:1(55.4%), d18:1(19.3%), br-d18:1 (25.3% ) (Ref. 1058)
57
GalNAcb1-4(NeuAc2-3)Galb1-3GalNAcb1-4(NeuGc2-3)Galb1-4GlcCer
GSG1036
Kazuo Nakamura
GalNAc-GD1a(Neu5Ac/Neu5Gc)
Download ChemDraw structure file

500MHz 1H, 125Hz 13C-NMR, HSQC, ROESY (Ref. 1059)



Bovine brain (0.12% of total gangliosides) (Ref. 1059)




58
GalNAcb1-4(NeuGc2-3)Galb1-3GalNAcb1-4(NeuAc2-3)Galb1-4GlcCer
GSG1037
Kazuo Nakamura
GalNAc-GD1a(Neu5Gc/Neu5Ac)
Download ChemDraw structure file

500MHz 1H, 125Hz 13C-NMR, HSQC, ROESY (Ref. 1059)



Bovine brain (0.08% of total ganglioseides) (Ref. 1059)




59
Gala1-3(Fuca1-2)Galb1-3Galb1-4GlcCer
GSG1038
Kazuo Nakamura
Download ChemDraw structure file
Blood group B acitive. Anti-B antibody stains blastula cell (Ref. 1060)
400MHz 1H (Ref. 1060)
(-)FAB-MS (Ref. 1060)


Blastula cells of Xenopus laevis (Ref. 1060)



An upper band on TLC, hydroxy fatty acid 46.3% (22h:0, 24h:0); a lower band on TLC, hydroxy fatty acid 66.3% (22h:0, 24h:0, 24h:1) (Ref. 1060)
60
GalNAcb1-3Gala1-3(Fuca1-2)Galb1-3GalNAcb1-4Galb1-4GlcCer
GSG1039
Kazuo Nakamura
Download ChemDraw structure file
Blood group B active (Ref. 1061)
400MHz 1H
[Spectrum 0003] (Ref. 1061)

TLC (Ref. 1061)
Rat (Wister/Furth) testis (Ref. 1061)



Fatty acids 16:0 to 24:0 (hydroxy and non-hydroxy), 16:0, 24:0, 16h:0, 24h:0

LCB d18:0, t18:0 (Ref. 1061)
61
KDN2-3Galb1-3GalNAcb1-4(KDN2-3)Galb1-4GlcCer
GSG1042
Kazuo Nakamura
KDNGDla
Download ChemDraw structure file
Reacted with mAb. kdn3G (KDNa2-3Galb1-epitope). Expression of KDN-gangliosides are changed during spermatogenesis. KDN/NeuAcGD1a is found in testis throughout all satages during spermatogenesis (Ref. 1064)
500MHz 1H-NMR: terminal KDN: H-3ax 1.55ppm,H-3eq 2.45ppm, innner KDN: H-3eq 2.61ppm (Ref. 1064)
FAB-MS intact and methylated (Ref. 1064)


Rainbow trout testis (Ref. 1064)



Ceramides A: C16:0 (20%) /C24:0 (80%) and d18:1 (80%)/ t18:0 (20%) b: C16:0 (1% )/C24:0 (99% ) and d18:1 (97%)/ t18:0 (3% ) (Ref. 1064)
62
KDN2-3Galb1-3GalNAcb1-4(Neu5Ac2-3)Galb1-4GlcCer
GSG1043
Kazuo Nakamura
(KDN,Neu5Ac)GD1a
Download ChemDraw structure file
Reacted with mAb. kdn3G (KDNa2-3Galb1-epitope). Expression of KDN-gangliosides are changed during spermatogenesis. KDN/NeuAcGD1a is found in testis throughout all satages during spermatogenesis (Ref. 1064)
500MHz 1H-NMR:terminal KDN:H-3ax 1.55ppm,H-3eq 2.45ppm, innner NeuAc:H-3eq 2.61ppm (Ref. 1064)
FAB-MS intact and methylated (Ref. 1064)


Rainbow trout testis (Ref. 1064)



Ceramides C24:1(99%) - d18:1(80%)/t18:0(20%), C16:0(36%)/24:1(64%) - d18:1/t18:0 (Ref. 1064)
63
NeuAc2-3Galb1-3GalNAcb1-4(KDN2-3)Galb1-4GlcCer
GSG1044
Kazuo Nakamura
(Neu5Ac,KDN)GD1a
Download ChemDraw structure file
Reacted with mAb. kdn3G (KDNa2-3Galb1-epitope). Expression of KDN-gangliosides are changed during spermatogenesis.(Ref. 1064)
500MHz 1H-NMR:terminal NeuAc:H-3eq 2.72ppm, innner KDN: H-3ax 1.62ppm,H-3eq 2.59ppm (Ref. 1064)
FAB-MS intact and methylated (Ref. 1064)


Rainbow trout testis (Ref. 1064)



Ceramides 24:1(99%)- d18:1(80% )/t18:0(20%), C16:0(36% )/24:1(64%)- d18:1 /t18:0 (Ref. 1064)
64
KDN2-3Galb1-3(KDN2-6)GalNAcb1-4Galb1-4GlcCer
GSG1045
Kazuo Nakamura
KDN GD1a2
Download ChemDraw structure file
Reacted with mAb. kdn3G (KDNa2-3Galb1-epitope). Expression of KDN-gangliosides are changed during spermatogenesis. KDN GDla emerged at later stage of development, 2-3 months prior to spermiation. (Ref. 1064)
500MHz 1H-NMR: terminal KDN: H-3ax 1.19ppm,H-3eq 2.53ppm, inner KDN:H-3ax 1.30ppm,H-3eq 2.62ppm (Ref. 1064)
FAB-MS intact and methylated (Ref. 1064)


Rainbow trout testis (Ref. 1064)



Ceramide 16:0 (1%)/24:1 (99%) - d18:1 (97% )/t18:0 (3%), 16:0 (54% )/24:1 (46%) - d18:1 /t18:0 (Ref. 1064)
65
KDNa2-3Galb1-3(Neu5Ac2-6)GalNAcb1-4Galb1-4GlcCer
GSG1046
Kazuo Nakamura
(KDN,Neu5Ac)GD1a2
Download ChemDraw structure file
Reacted with mAb. kdn3G (KDNa2-3Galb1-epitope). Expression of KDN-gangliosides are changed during spermatogenesis. KDN GDla emerged at later stage of development, 2-3 months prior to spermiation. (Ref. 1064)
500MHz 1H-NMR:terminal KDN:H-3ax 1.18ppm,H-3eq 2.51ppm, innner NeuAc:H-3ax 1.33ppm, H-3eq 2.75ppm (Ref. 1064)
FAB-MS. intact and methylated (Ref. 1064)


Rainbow trout testis (Ref. 1064)



Ceramide 16:0(2%)/24:1(98%)-d18:1(97%)/t18:0(3%),16:0(71%)/24:1(29%)-d18:1 /t18:1 (Ref. 1064)
66
3-O-Methyl-Gala1-3[6'-O-(2-aminoethylphosphonyl)Gala1-2](2-aminoethylphosphonyl-6)Galb1-4(2-aminoethylphosphonyl-6)GlcCer
GSG1047
Kazuo Nakamura
Download ChemDraw structure file

400MHz 1H (HF treated sample). COSY.
[Spectrum 0002] (Ref. 1065)
(-)FAB-MS [[Sp0001] (Ref. 1065)

Eggs of Aplysia kurodai (sea hare) (Ref. 1065)



Fatty acids 16:0(43.9%), 17:0(7.6%), 18:0(45.0%) (Ref. 1065)

LCB d18:1(21.7%), 16-Methyl d19:1(45.5%), d18:1 (21.7%), 16-Methyl d19:1(45.5% ) (Ref. 1065)
67
Mana1-2Gala1-6GlcNa1-4GlcCer
GSG1048
Kazuo Nakamura
Download ChemDraw structure file

1H, 13C (Ref. 1066)
LD-MS (Ref. 1066)


Sphingomonas paucimobilis (synonym: Pseudomonas paucimobilis, bacterium) (Ref. 1066)



Fatty acids 14h:0
LCB d18:0, d18:1 (Ref. 1066)
68
Galb1-3(2-aminoethylphosphonyl-6)Mana1-3Mana1-4(2-aminoethylphosphonyl-6)GlcNa1-6Ino-phospho-Cer
GSG1049
Kazuo Nakamura
Download ChemDraw structure file





Leptomonas samueli (protozoan) (Ref. 1068)




69
2-Aminoethylphosphony-6Mana1-3Mana1-4(2-aminoethylphosphonyl-6)GlcNa1-6Ins-phospho-Cer
GSG1050
Kazuo Nakamura
Download ChemDraw structure file

600MHz 1H, COSY, ROESY, COSY-45, 13C-NMR (Ref. 1068)
FAB-MS (Ref. 1068)


Leptomonas samueli (protozoan) (Ref. 1068)



Fatty acids 18:0(21.2%), 24:0(26.0%) (Ref. 1068)

LCB br-C19:0(7.7%), t20:0, t21:0 (Ref. 1068)
70
Fuca1-4(3-phosphoethanolaminyl)Inoa1-phospho-Cer
GSG1051
Kazuo Nakamura
Download ChemDraw structure file

1H-NMR 31P-NMR HOHAHA, COSY, NOE, ROESY, 2-d long-range 1H{31P}scalarcorelation (Ref. 1069)
LAIMS, CID MS/MS (Ref. 1069) FAB-MS, FAB MS/MS (Ref. 1067)


Tritrichomonas foetus (protozoan) (Ref. 1067/1069)



Ceramides C16:0-d18:0, C16:0-d18:1 (Ref. 1067)
71
3-phospho-Ino-phospho-Cer
GSG1052
Kazuo Nakamura
Download ChemDraw structure file


CID-MS (Ref. 1067), LAIMS (Ref. 1069)


Tritrichomonas foetus (protozoan) (Ref. 1067/1069), Trichomonas vaginalis (protozoan) (Ref. 1069)



Ceramides C16:0-d18:0, C16:0-d18:1
72
3-phosphoethanolaminyl-Inoa1-phospho-Cer
GSG1053
Kazuo Nakamura
Download ChemDraw structure file


CID MS/MS (Ref. 1069)


Trichomonas vaginalis (protozoan) (Ref. 1069)



Ceramides C16:0-d18:0, C16:0-d18:1(Ref. 1069)
73
GlcUa1-3Glca1-4Xylb1-4Xylb1-4(Rhaa1-3)Mana1-2Mana1-3(2-AEPl-6)Mana1-3Mana1-4(2-AEPl-6)GlcNa1-6Ino(1or2)-phospho-Cer
GSG1054
Kazuo Nakamura
Download ChemDraw structure file

1H-NMR(500MHz) 13C-NMR : COSY, TOCSY, ROESY (Ref. 1070)
FAB-MS (Ref. 1070)


Promastigotes of Leptomonas samueli (protozoan) (Ref. 1070)




74
Xylb1-3Xylb1-4Xylb1-4(Rhaa1-3)Mana1-2Mana1-3(2-AEPl-6)Mana1-3Mana1-4(2-AEPl-6)GlcNa1-6Ino(1or2)-phospho-Cer
GSG1055
Kazuo Nakamura
Download ChemDraw structure file

500MHz 1H-NMR, 13C-NMR : TOCSY, COSY, ROESY (Ref. 1070)
FAB-MS (Ref. 1070)


Promastigotes of Leptomonas samueli (protozoan) (Ref. 1070)




75
Xylb1-4Xylb1-4(Rhaa1-3)Mana1-2Mana1-3(2-AEPl-6)Mana1-3Mana1-4(2-AEPl-6)GlcNa1-6Ins(1or2)-phospho-Cer
GSG1056
Kazuo Nakamura
Download ChemDraw structure file

500MHz 1H-NMR, 13C-NMR : TOCSY, COSY, ROESY (Ref. 1070)
FAB-MS (Ref. 1070)


Promastigotes of Leptomonas samueli (protozoan) (Ref. 1070)




76
OPHIDIACEREBROSIDE
Glucosylceramide/(2S,3R,4E,8E,10E)-1-(b-D-glucopyranosyloxy)-3-hydroxy-2[((r)-2-hydroxydocosanoyl)amino]-9-methyl-4,8,10-octadecatriene
GSG1057
Kazuo Nakamura
Download ChemDraw structure file
Cytotoxic for murine leukemia cell L1210 (Ref. 1071)




Ophidiaster ophidiamus (starfish) (Ref. 1071)



(2S,3R,4E,8E,10E)-1-(b-D-)-3-hydroxy-2[((r)-2-hydroxydocosanoyl)amino]-9-methyl-4,8,10-octadecatriene
77
Galb1-3(NeuAc2-6)GalNAcb1-4Galb1-4GlcCer
GSG1059
Kazuo Nakamura
GM1a
Download ChemDraw structure file
Reactive with anti-cholinergic neuron specific antibody (anti-Chol-1) (Ref. 1074)

FAB-MS(-) (Ref. 1074)

Mobility on TLC with (C:M:12mM MgCl2=5:4:1), between GM1 and GD1a (Ref. 1074)
Bovine brain (Ref. 1074)



Ceramides C18:0-d20:1, C18:0-d18:1
78
Galb1-3(NeuAc2-6)GalNAcb1-4(NeuAc2-3)Galb1-4GlcCer
GSG1060
Kazuo Nakamura
GD1aa
Download ChemDraw structure file
Reactive with anti-cholinergic neuron specific antibody (anti-Chol-1) (Ref. 1074)

FAB-MS(-) (Ref. 1074)

Mobility on TLC with C:M:12mM MgCl2=5:4:1, higher than GD1b (Ref. 1074)
Bovine brain (Ref. 1074)



Ceramide C18:0-d18:1 (Ref. 1074)
79
Galb1-3(NeuAc2-6)GalNAcb1-4(NeuGc2-8NeuAc2-3)Galb1-4GlcCer
GSG1061
Kazuo Nakamura
GT1ba
Download ChemDraw structure file
Reactive with anti-cholinergic neuron specific antibody (anti-Chol-1) (Ref. 1074)

FAB-MS(-) (Ref. 1074)

mpbolity on TLC with (C:M:12mM MgCl2=5:4:1), between GT1b and GQ1b (Ref. 1074)
Bovine brain (Ref. 1074)



Ceramides C18:0-d20:1, C18:0-d18:1 (Ref. 1074)
80
NeuAc2-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1062
Kazuo Nakamura
X0 ganglioside, sLex-8
Download ChemDraw structure file
Reactive with mAb CSLEX1 (which recognizes sialyl Lewis x structure). Not reactive with mAb CDW65 (VIM-2 specific) nor CD15 (anti-sialyl Lewis x). Strong riactivity with mAb AM3 (which recognizes sialyl Lewis x sequence). (Ref. 1075)

FAB-MS(+) (Ref. 1075)


Human granulocyte (Ref. 1075)



Ceramides C16:0-d18:1 (Ref. 1075)
81
NeuAc2-3Galb1-4GlcNAcb1-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1063
Kazuo Nakamura
Download ChemDraw structure file
Reactive with mAb CDW65 (i.e. having VIM-2 motif), but not reactive with mAb CSLEX1 (which recognize the sialyl Lewis x structure) (Ref. 1075)

FAB-MS(+) of permethylated samples. spectrum is not shown. Text only. [MH]+=2980,[Mna]+=3002,[NeuAcGalG1cNAc]+=1448, close spots on TLC gave ion peaks [MH]+=2870 and [Mna]+=2892 (difference of fatty acid) (Ref. 1075)


Human granulocyte (Ref. 1075)



Ceramides 24:0-d18:1, 16:0-d18:1 (Ref. 1075)
82
NeuAc2-6GlcCer
GSG1064
Kazuo Nakamura
Download ChemDraw structure file

1H-NMR Glc,H-1,J1.2=84Hz(d=1.14ppm) blinkage (Ref. 1076)
FAB-MS(-) [M-H]-=1033, 1047, 1061, 1075, 1089 corresponding to C18:1, C19:1, C20:1, C21:1, C22:1, respectively. Long chain base is t18:0 (Ref. 1076)


Sperm of Hemicentrotus pulcherrimus (sea urchin) (Ref. 1076),sea urchin (anthocidaris crassispina) spermatozoa(Ref. 1136)



Fatty acids 20:1(30mol%), 21:1(20mol%), 22:1(30mol%) (Ref. 1076)

LCB t18:0 (Ref. 1076)
83
NeuAc2-8NeuAc2-6GlcCer
GSG1065
Kazuo Nakamura
Download ChemDraw structure file

1H-NMR Glc H-1,J1.2=7.3Hz (d=4.12ppm) blinkage (Ref. 1076)
FAB-MS(-) [M-H]-=1325, 1339, 1353, 1367, 1381(corresponding ot C18:1, C19:1, C20:1, C21:1, C22:1, respectively) Long chain base is t18:0 (Ref. 1076)


Sperm of Hemicentrotus pulcherrimus (sea urchin) (Ref. 1076)



Fatty acids 20:1, 21:1, 22:1 (Ref. 1076)

LCB t18:0 (Ref. 1076)
84
NeuAc2-8NeuAc2-8NeuAc2-6GlcCer
GSG1066
Kazuo Nakamura
Download ChemDraw structure file


FAB-MS(+) of permethylated samples. NeuAc=376, (NeuAc)2=737, (NeuAc)3=1099,
2H-acetylated samples gave peaks corresponding to lactonyzed (Neu5Ac)3(Hex) (Ref. 1076)


Sperm of Hemicentrotus pulcherrimus (sea urchin) (Ref. 1076)




85
HSO3-8NeuAc2-6GlcCer
GSG1067
Kazuo Nakamura
Download ChemDraw structure file

1H-NMR Glc,H-1, d=4.10ppm, J1.2=8.4Hz(blinkage),NeuAc,H-3eq, d=2.48ppm,H-3axd=1.45ppm(alinkage) (Ref. 1076)
[M-H]-=1113, 1127, 1141, 1155, 1169 (corresponding to C18:1, C19:1, C20:1, C21:1, C22:1, respectively. long chain base is t18:0) (Ref. 1076)


Sperm of Hemicentrotus pulcherrimus (sea urchin) (Ref. 1076)



Fatty acids C20:1 C21:1, C22:1 (Ref. 1076)

LCB t18:0 (Ref. 1076)
86
NeuAc2-8NeuAc2-8NeuAc2-8NeuAc2-6GlcCer
GSG1068
Kazuo Nakamura
Download ChemDraw structure file

1H-NMR Glc, H-1, d=4.10ppm, J1.2=8.4Hz ; NeuAc, H-3eq, 2.48ppm, H-3ax, 1.45ppm (Ref. 1076)
FAB-MS(-) [M-H]-=1113, 1127, 1141, 1155, 1169(corresponding to C18:1, C19:1, C20:1, C21:1, C22:1, respectively. Long chain base : t18:0) (Ref. 1076)


Sperm of Hemicentrotus pulcherrimus (sea urchin) (Ref. 1076)




87
HSO3-8NeuAc2-8NeuAa2-6GlcCer
GSG1069
Kazuo Nakamura
Download ChemDraw structure file

1H-NMR
FAB-MS(-) [M-H]-=1387, 1401, 1415, 1429, 1443 (corresponding to C18:1, C19:1, C20:1, C21:1, C22:1, respectively. long chain base is t18:0. Ion peaks corresponding to lactonized molecules were detedted (Ref. 1076)


Sperm of Hemicentrotus pulcherrimus (sea urchin) (Ref. 1076)



Fatty acids 20:1, 21:1, 22:1 (Ref. 1076)

LCBt18:0 (Ref. 1076)
88
Gala1-2Ins-phospho-Cer
GSG1071
Kazuo Nakamura
Download ChemDraw structure file

OH- 3400,1040cm-1; amide I 1650cm-1; amide II 1550cm-1, phospnate; 1220cm-1 (Ref. 1078)
Gal, H-1, 5.05ppm(J1.2=3.30Hz) (Ref. 1078)
FAB-MS(-) [M-H]-=1070, 1056, P-Cer derived ions M/Z = 746,732 (Ref. 1078)


Ascaris suum (porcine roundworm) (Ref. 1078)



Fatty acids 16:0(1.4%), 18:0(1.7%), 24:0(25.1%), 22h:0(5.6%), 23h(0.3%), 24h:0 (63.2%) (Ref. 1078)

LCB, br-d17:0(30.7%), d18:0(69.3% ) (Ref. 1078)
89
Spirometoside
Galb1-4(Fuca1-3)Glcb1-3(Galb1-6)GalCer
GSG1072
Kazuo Nakamura
Download ChemDraw structure file

FAB-MS(-),[M-H]-=1472,1498 (C26:0-d18:0,C28:1,C28:0-D18:0)
[Spectrum 0001]and 1488,1514(C26:-t18:0,C28:1-t18:0)(Ref. 1079)

Plerocercoids of Spirometra erinacei (cestode) (Ref. 1079)



Fatty acids Upper band on TLC: C28:1(30.2%), C26:0 (21.9%)/d18:0(45.1%),t18:0(54.9%). Lower band on TLC: C28:0(21.7%), C26:0(10.3%), C18:1(13.8%), C16:0(11.0%)/t18:0(90.3%) (Ref. 1079)

90
Ac-O-9-NeuGc2-3Galb1-4GlcCer
GSG1073
Kazuo Nakamura
9-O-Ac GM3(GC)
Download ChemDraw structure file

Methylane proton of NeuGc C-9 shifted to lower field (H-9a,3.95ppm, H-9b,4.22ppm) (Ref. 1080)
FAB-MS(-) [M-H-]=1321,[HexHexCer-H]-=972 (Ref. 1080)


Equine erythrocytes (Ref. 1080)



Fatty acid C24:0(32.2%) (Ref. 1080)

LCB d18:1(98.7%) (Ref. 1080)
91
Ac-O-6'-NeuGca1-3Galb1-4GlcCer
GSG1074
Kazuo Nakamura
6'-O-Ac GM3(GC)
Download ChemDraw structure file

FAB-MS(-) [Ac-HexHexCer-H]-=1014(Ref. 1080)


Equine erythrocytes (Ref. 1080)



Fatty acid 24:0(26.8%) (Ref. 1080)
d18:1(97.5%) (Ref. 1080)
92
2-O-Acyl-b-D-glucopyranosylceramide
GSG1075
Kazuo Nakamura
Download ChemDraw structure file

Carbonyl ester1738cm-1, -CH stretching, 2922; 2852cm-1(Ref. 1004)



Alaskan pollack brain (Ref. 1004)



Fatty acic and sphingoid comopsition (Ref. 1004)
Fatty acic and sphingoid comopsition (Ref. 1004)
93
3-O-Acyl-b-D-glucopyranosylceramide
GSG1076
Kazuo Nakamura
Download ChemDraw structure file

carbonyl ester,1738cm-1; -CH stretching 2922, 2852cm-1 (Ref. 1004)




Alaskan pollack brain (Ref. 1004) porcine and human epidermis (Ref. 1016)



Fatty acic and sphingoid comopsition (Ref. 1004)
Fatty acic and sphingoid comopsition (Ref. 1004)
94
6-O-Acyl-b-D-glucopyranosylceramide
GSG1077
Kazuo Nakamura
Download ChemDraw structure file

Carbonyl ester,1738cm-1; -CH stretching 2922, 2852cm-1 (Ref. 1004)




Alaskan pollack brain (Ref. 1004)Spleen of Gaucher disease patient (Ref. 1015)



Fatty acic and sphingoid comopsition (Ref. 1004)
Fatty acic and sphingoid comopsition (Ref. 1004)
95
2-O-acyl-b-D-galactopyranosylceramide
GSG1078
Kazuo Nakamura
Download ChemDraw structure file

1730cm-1 carbonyl ester (Ref. 1004)



TLC (Ref. 1004)
Alaskan pollack brain (Ref. 1004) human and bovine brain (Ref. 1013) whale brain (Ref. 1014)



Fatty acic and sphingoid comopsition (Ref. 1004)
Fatty acic and sphingoid comopsition (Ref. 1004)
96
3-O-acyl-b-D-galactopyranosylceramide
GSG1079
Kazuo Nakamura
Download ChemDraw structure file

[a]DIN CHCl3 FrII.=-5.0, FrIII.=+3.0, FrIV.=+0.6 (Ref. 0002)
carbonyl ester, 1730cm-1; amide1640cm-1 (Ref. 1002/1004)



Bovine brain (Ref. 1001/1002/1003) 1.1% of sphingolipid fraction of bovine brain (Ref. 1002) human brain (Ref. 1011/1013) Alaskan pollack brain (Ref. 1004) porcine stomach (Ref. 1012) whale brain (Ref. 1014)



Fatty acic and sphingoid comopsition (Ref. 1002/1003/1004/1011)
Fatty acic and sphingoid comopsition (Ref. 1002/1003/1004/1011)
97
4-O-acyl-b-D-galactopyranosylceramide
GSG1080
Kazuo Nakamura
Download ChemDraw structure file

carbonyl ester, 1738cm-1; -CH Stretching 2922,2852cm-1(Ref. 1004)



Alaskan pollack brain (Ref. 1003/1004), porcine stomach(Ref. 1012) human and bovine brain (Ref. 1013) whale brain (Ref. 1014)



Fatty acic and sphingoid comopsition (Ref. 1004)
Fatty acic and sphingoid comopsition (Ref. 1004)
98
6-O-acyl-b-D-galactopyranosylceramide, Acyl-O-6-Galb1-1Cer
GSG1081
Kazuo Nakamura
Download ChemDraw structure file

[a]DIN CHCl3 FrII.=-5.0, FrIII.=+3.0, FrIV.=+0.6 (002)
1730cm-1 carbonyl ester,1640,1530cm-1 amide (Ref. 1001/1002/1004)




Bovine brain (Ref. 1001/1002/1008/1013)1.1% of sphingolipid fraction of bovine brain (Ref. 1002)Alaskan pollack and Pasific cod brain (Ref. 1003/1004)distributin in Alaskan pollack brain (Ref. 1003)Alaskan pollack brain (molecular species) (Ref. 1004)human brain (Ref. 1009/1011/1013)porcine brain (Ref. 1010/1017) porcine stomach (Ref. 1012)whale brain (Ref. 1014)Brain (Ref. 1010), pig stomach mucosa(Ref. 1012)



Combiantion of hydroxy and non-hydorxy (Ref. 1001/1002), fatty acid and sphingoid (Ref. 1002/1004/1010)
99
Spirometoside
Galb1-4(Fuca1-3)Glcb1-3GalCer
GSG1084
Kazuo Nakamura
Download ChemDraw structure file

1H 1D-NMR; intact(A) and lyso(B)
[Spectrum 0002], TOCSY
[Spectrum 0003], ROESY
[Spectrum 0004](Ref. 1027)
Intact (-)FAB-MS
[Spectrum 0001](Ref. 1027)

Plerocercoids of Spirometra erinacei (cestode) (Ref. 1027)



Fatty acids 18:0(30.6%), 18:1(24.2%), 18h:0(13.9%) (Ref. 1027)

LCB d18:0(44.4%), t18:0(55.6%) (Ref. 1027)
100
NeuAc2-3Galb1-3(NeuAc2-6)GalNAcb1-4(NeuAc2-3)Galb1-4GlcCer
GSG1085
Kazuo Nakamura
GT1aa
Download ChemDraw structure file
Cholinergic-specific antigen Chol-1a-a (Reacted with anti-cholinergic neuron specific antibody) (Ref. 1028)
Monoclonal antibody: GGR-41 (reacted also with GQ1ba) (Ref. 1124)
INTACT FAB-MS
[Spectrum 0001] (Ref. 1026/1028)

Dogfish (shark) (Squalus acanthias) brain (Ref. 1026) bovine brain (Ref. 1028) Rat liver (Ref. 1123)
Rat: intense immunoreactivity was found in the neuropil of the spinal cord dorsal horn, spinal trigeminal nucleus, solitary tract nucleus, superior colliculus, interpeduncular nucleus, hypothalamus and septal area(Ref. 1124)
The suitably protected sialyl alpha-(2-->6) ganglioside was glycosylated with the phenylthioglycoside of sialic acid in the presence of N-iodosuccinimide (NIS)-trimethylsilyl trifluoromethanesulfonate (TMSOTf), followed by further glycosylation with the methyl thioglycoside promoted by dimethyl(methylthio)sulfonium triflate (DMTST), to give the heptasaccharide. The oligosaccharide obtained was converted into the title ganglioside by the introduction of ceramide and then complete deprotection. (Ref. 1128)


Fatty acids 16:0(15.0%), 16:1(9.3%), 18:0(8.6%), 18:1(9.0%), 22:1(38.4%), 24:0(13%), 24:1(6.7%) (Ref. 1026)

LCB d18:0(43%) , d18:1(57%) (Ref. 1026)
101
Galb1-3GalNAcb1-4(HSO3-3)Galb1-4GlcCer
GSG1086
Kazuo Nakamura
Download ChemDraw structure file










102
NeuAca2-3Galb1-3GalNAcb1-4GalCer
GSG1087
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocytes(Ref. 1091)




103
GalNAcb1-4(NeuAca2-3)Galb1-3GalNAcb1-4Galb1-4GlcCer
GSG1088
Kazuo Nakamura
GalNAc-GM1b
Download ChemDraw structure file





Human brain (Ref. 1100), (Ref. 1092)




104
NeuAca2-3Galb1-4GlcCer
GSG1089
Kazuo Nakamura
GM3
Download ChemDraw structure file


MALDI-TOFMS
[Spectrum 0001] (T.Taketomi) Method (Ref. 3072)






105
GalNAcb1-4(NeuAca2-3)Galb1-4GlcCer
GSG1090
Kazuo Nakamura
GM2
Download ChemDraw structure file


MALDI-TOFMS
[Spectrum 0001] (T.Taketomi) Method (Ref. 3072)






106
Galb1-3GalNAcb1-4(NeuAca2-3)Galb1-4GlcCer
GSG1091
Kazuo Nakamura
GM1
Download ChemDraw structure file
Binding to: tetanus toxin (Ref. 1149), cholera toxin(Ref. 1150), botulinum toxin (Ref. 1151), interaction with hormones (FSH, LH, HCG) <<>>

MALDI-TOFMS
[Spectrum 0001] (T.Taketomi) (Ref. 3072)


peripheral nerve myelin(Ref. 1144), myelin(Ref. 1145), human leukemic polymorphonuclear leukocytes(Ref. 1146), synaps(Ref. 1147/1394) (Ref. 1094)




107
Galb1-3GalNAcb1-4(2aminoethylphosphoryl-6)GlcNAcb1-3Manb1-4GlcCer
GSG1092
Kazuo Nakamura
Download ChemDraw structure file





Pupae of Calliphora vicina (Insecta: Diptera)(Ref. 1490)




108
Galx1-3Galb1-3GalNAcb1-4(NeuAca2-3)Galb1-4GlcCer
GSG1093
Kazuo Nakamura
Gal-GM1
Download ChemDraw structure file





fat tissue (Ref. 1096)




109
Galx1-3(Fuca1-2)Galb1-3GalNAcb1-4(NeuAca2-3)Galb1-4GlcCer
GSG1094
Kazuo Nakamura
Download ChemDraw structure file





rat liver and in rat hepatoma induced by N-2-acetylaminofluorene(Ref. 1097)




110
Galb1-3Galx-3Galb1-3GalNAcb1-4(NeuAca2-3)Galb1-4GlcCer
GSG1095
Kazuo Nakamura
Download ChemDraw structure file





fat tissue (Ref. 1096)




111
Galx1-3Galb1-3Galx1-3GalNAcb1-4(NeuAca2-3)Galb1-4GlcCer
GSG1096
Kazuo Nakamura
Download ChemDraw structure file





fat tissue (Ref. 1096)




112
NeuAca2-3Galb1-3GalNAcb1-4(NeuAca2-3)Galb1-4GlcCer
GSG1097
Kazuo Nakamura
GD1a
Download ChemDraw structure file


MALDI-TOFMS
[Spectrum 0001] (T.Taketomi) Method (Ref. 3072)






113
NeuAca2-8NeuAca2-3Galb1-3GalNAcb1-4(NeuAca2-3)Galb1-4GlcCer
GSG1098
Kazuo Nakamura
GT1a
Download ChemDraw structure file





Human brain(Ref. 1099)




114
GalNAcb1-4(NeuAca2-3)Galb1-3GalNAcb1-4(NeuAca2-3)Galb1-4GlcCer
GSG1100
Kazuo Nakamura
GalNAc-GD1a
Download ChemDraw structure file


MALDI-TOFMS
[Spectrum 0001] (T.Taketomi) Method (Ref. 3072)


Human plasma, red cells, muscle, brain(2 micro moles/kg wet wt), peripheral nerve (femoral nerve)(23micro moles/kg wet wt)(Ref. 1183), human brain(Ref. 1101)




115
NeuAca2-8NeuAca2-3Galb1-4GlcCer
GSG1101
Kazuo Nakamura
GD3
Download ChemDraw structure file


MALDI-TOFMS
[Spectrum 0001] (T.Taketomi) Method (Ref. 3072)






116
GalNAcb1-4(NeuAca2-8NeuAca2-3)Galb1-4GlcCer
GSG1102
Kazuo Nakamura
GD2
Download ChemDraw structure file


MALDI-TOFMS
[Spectrum 0001] (T.Taketomi) Method (Ref. 3072)






117
Galb1-3GalNAcb1-4(NeuAca2-8NeuAca2-3)Galb1-4GlcCer
GSG1103
Kazuo Nakamura
GD1b
Download ChemDraw structure file


MALDI-TOFMS
[Spectrum 0001] (T.Taketomi) Method (Ref. 3072)


Human brain (Ref. 1098/1130), Bovine adrenal medula(Ref. 1131)




118
Fuca1-2GalNAcb1-4(NeuAca2-8NeuAca2-3)Galb1-4GlcCer
GSG1104
Kazuo Nakamura
Fuc-GD1b
Download ChemDraw structure file





Pig cerebellum<1182>(Ref. 1103)



Fatty acids 18:0(80.4%), 20:0(16.0%)

LCB d18:1(60%), d20:1(40%)
119
NeuAca2-3Galb1-3GalNAcb1-4(NeuAca2-8NeuAca2-3)Galb1-4GlcCer
GSG1105
Kazuo Nakamura
GT1b
Download ChemDraw structure file









120
NeuAca2-8NeuAca2-3Galb1-3GalNAcb1-4(NeuAca2-8NeuAca2-3)Galb1-4GlcCer
GSG1106
Kazuo Nakamura
GQ1b
Download ChemDraw structure file





Fish brain(Ref. 1104)




121
NeuAca2-8NeuAca2-8NeuAca2-3Galb1-4GlcCer
GSG1107
Kazuo Nakamura
GT3
Download ChemDraw structure file





Fish brain(Ref. 1105)




122
GalNAcb1-4(NeuAca2-8NeuAca2-8NeuAca2-3)Galb1-4GlcCer
GSG1108
Kazuo Nakamura
GT2
Download ChemDraw structure file





Pig adipose tissue(Ref. 1106), fish brain(Ref. 1133)




123
Galb1-3GalNAcb1-4(NeuAca2-8NeuAca2-8NeuAca2-3)Galb1-4GlcCer
GSG1109
Kazuo Nakamura
GT1c
Download ChemDraw structure file





Cod fish brain (Ref. 1104)




124
NeuAca2-8NeuAca2-3Galb1-3GalNAcb1-4(NeuAca2-8NeuAca2-8NeuAca2-3)Galb1-4GlcCer
GSG1110
Kazuo Nakamura
GP1c
Download ChemDraw structure file





Cod fish brai(Ref. 1104)




125
NeuAca2-6(NeuAca2-3)Galb1-3GalNAcb1-3Gala1-4Galb1-4GlcCer
GSG1111
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocytes (Ref. 1107)




126
NeuAca2-6Galb1-3GalNAcb1-3Gala1-3Galb1-4GlcCer
GSG1112
Kazuo Nakamura
Download ChemDraw structure file





rat small intestine(Ref. 1201)




127
NeuAca2-3Galb1-3GlcNAcb1-3Galb1-4GlcCer
GSG1113
Kazuo Nakamura
Download ChemDraw structure file





Human carcinomas(Ref. 1109)




128
NeuAca2-3Galb1-3(Fuca1-4)GalNAcb1-4Galb1-4GlcCer
GSG1114
Kazuo Nakamura
Sialyl-Lea
Download ChemDraw structure file





Gastrointestinal cancer(Ref. 1110)




129
Galb1-3(NeuAca2-6)(Fuca1-4)GlcNAcb1-3Galb1-4GlcCer
GSG1115
Kazuo Nakamura
Download ChemDraw structure file





Human adenocarcinoma(Ref. 1111)




130
NeuAca2-8NeuAca2-3Galb1-3GlcNAcb1-3Galb1-4GlcCer
GSG1116
Kazuo Nakamura
Download ChemDraw structure file









131
NeuAca2-3Galb1-3(NeuAca2-6)GlcNAcb1-3Galb1-4GlcCer
GSG1117
Kazuo Nakamura
Download ChemDraw structure file





Human adenocarcinoma(Ref. 1111)




132
sialosylparagloboside
NeuAca2-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1118
Kazuo Nakamura
Download ChemDraw structure file









133
NeuAca2-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcCer
GSG1119
Kazuo Nakamura
sLex-6
Download ChemDraw structure file





Human kidney(Ref. 1114/1211), adenocarcinoma (Ref. 1212), leukocytes (Ref. 1213)



Fatty acids 16:0(24%)
134
NeuAca2-8NeuAca2-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1120
Kazuo Nakamura
Download ChemDraw structure file





Human kidney(Ref. 1184), Hog kidney (Ref. 1115), Human erythrocytes (Ref. 1107)




135
NeuAca2-8NeuAca2-8NeuAca2-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1121
Kazuo Nakamura
Download ChemDraw structure file





Hog kidney cortex(Ref. 1115)




136
NeuAca2-3Galb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1122
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocyte membranes(Ref. 1090)




137
NeuAca2-3GalNAcx1-3Galb1-4GlcNAcb1-3(Fuca1-2)Galb1-4GlcCer
GSG1123
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocytes (Ref. 1116)




138
NeuAca2-6Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1124
Kazuo Nakamura
Download ChemDraw structure file









139
Sialosyllactosaminylparagloboside, G6 ganglioside
NeuAca2-3Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1125
Kazuo Nakamura
Download ChemDraw structure file





Human spleen(Ref. 1117/1203), placenta(Ref. 1221), granulocytes(Ref. 1222); Bovine erythrocytes (Ref. 1223/1224); Chicken skeltal muscle(Ref. 1211)




140
NeuAca2-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcCer
GSG1126
Kazuo Nakamura
sialyl dimeric Lex
Download ChemDraw structure file





Human adenocarcinoma(Ref. 1118)




141
NeuAca2-6Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1127
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocyte membranes(Ref. 1090)




142
NeuAca2-6Galb1-4GlcNAcb1-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcCer
GSG1128
Kazuo Nakamura
Download ChemDraw structure file





Human adenocarocinoma (Ref. 1119)




143
NeuAc2-3Galb1-4GlcNAcb1-3(Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1129
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocyte membranes(Ref. 1120)




144
NeuAca2-3Galb1-4GlcNAcb1-3(Fucx1-xGalb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1130
Kazuo Nakamura
Download ChemDraw structure file





erythrocyte (Ref. 1121)




145
NeuAca2-3Galb1-4GlcNAcb1-3(NeuAca2-3Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1131
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocytes(Ref. 1107)




146
NeuAca2-3Galb1-4GlcNAcb1-3{Galx1-3(Fuca1-2)Galb1-4GlcNAcb1-6}Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1132
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocyte membranes(Ref. 1120)




147
9-O-Ac-KDN2-3Galb1-3GalNAcb1-4(KDN2-3)Galb1-4GlcCer
GSG1134
Kazuo Nakamura
Download ChemDraw structure file





Trout Ovarian Fluid




148
Ac-O-9NeuAca2-8NeuAca2-8NeuAca2-3Galb1-4GlcCer
GSG1135
Kazuo Nakamura
Ac-O-9GT3
Download ChemDraw structure file





Chicken and rat brain (Ref. 1424)




149
galgactocerebroside
Galb1-1Cer
GSG1136
Kazuo Nakamura
Download ChemDraw structure file




Rat(Ref. 1411/1412), human brain<<>>, distribution in human brain(Ref. 1413), alterlation with age (Ref. 1419), bovine axon(Ref. 1140), peripheral nerve (Ref. 1403/1414/1415), human kidney(Ref. 1416), neuron(Ref. 1418), (Ref. 1417). Pheretima hilgendorfi (earthworm) (Ref. 2061), Tylorrhynchus heterochetus (lugworm) (Ref. 2063)



Fatty acids Pheretima hilgendorfi (earthworm) 16:0(0.4%), 18:0(2.0%), 19:0(0.4%), 20:0(3.3%), 21:0(2.5%), 22:0(48.2%), 23:0(11.7%), 24:0(31.5%); br-d18:1(36.6%) (Ref. 2061)
Tylorrhynchus heterochetus (lugworm),16:0(82.3%), 17:0(8.5%), 18:0(9.2%) (Ref. 2063)

LCB Pheretima hilgendorfi (earthworm),br-d18:1(36.6%), d18:1(44.4%), br-d19:1(19.0%) (Ref. 2061)
Tylorrhynchus heterochetus (lugworm), d18:1(57.3%), d18:2(42.7%) (Ref. 2063)
150
Galb1-1Cer(sphingosine 3-O-Acyl)
GSG1138
Kazuo Nakamura
Download ChemDraw structure file





Brain (Ref. 1011/1002)




151
Galb1-1Cer(sphingosine 3-O-alkyl)
GSG1139
Kazuo Nakamura
Download ChemDraw structure file





Bovine brain (Ref. 1420)




152
Psychosine
Galb1-1Sphingosine
GSG1140
Kazuo Nakamura
Download ChemDraw structure file










153
glucocerebroside
Glcb1-1Cer
GSG1141
Kazuo Nakamura
Download ChemDraw structure file




Human, bovine, equine spleen (Ref. 1396/1400), spleen of Gaucher's disease patient (Ref. 1421), human brain (Ref. 1422), rat and bovine brain (Ref. 1423)




154
Galb1-3GalNAca1-4GalNAcb1-4(2aminoethylphosphoryl-6)GlcNAcb1-3Manb1-4GlcCer
GSG1142
Kazuo Nakamura
Download ChemDraw structure file





Pupae of Calliphora vicina (Insecta: Diptera)(Ref. 1490)larvae of the green-bottle fly, Lucilia caesar(Ref. 2060)




155
glucopsychosine
Glcb1-1Sphingosine
GSG1143
Kazuo Nakamura
Download ChemDraw structure file





Spleen of Gaucher's disease patient (Ref. 1387/1388), microsome from rat brain (Ref. 1389)




156
L-Fuca1-1Cer
GSG1144
Kazuo Nakamura
Download ChemDraw structure file





Human colon tumors(Ref. 1390)




157
Xylb1-1Cer
GSG1145
Kazuo Nakamura
Download ChemDraw structure file





salt gland of the herring gull(Ref. 1391)




158
Fuca1-3GalNAcb1-4(Fuca1-3)GlcNAcb1-4GlcCer
GSG1146
Kazuo Nakamura
Download ChemDraw structure file





<<>>




159
cytolipin H, lactosylceramide
Galb1-4Glcb1-1Cer
GSG1147
Kazuo Nakamura
LacCer
Download ChemDraw structure file




Structure (Ref. 1395), spleen and kidney (Ref. 1396/1137/1253), erythrocytes (Ref. 1397/1398); (Ref. 1399), human hepatoma tissue (Ref. 1401), human gastric carcinoma (Ref. 1402), human skeletal muscle (Ref. 1403), astroglia of rat brain (Ref. 1404), Bovine spleen(Ref. 1237), erythrocytes(Ref. 1238), kidney(Ref. 1239); Human adenocarcinoma(Ref. 1238), kidney(Ref. 1240), neutrophils(Ref. 1241)



160
Galabiosylceramide
Gala1-4Galb1-1Cer
GSG1148
Kazuo Nakamura
Download ChemDraw structure file
Level varies in mouse due to sex hormones(22)




kidney of a patient with Fabry's disease (Ref. 1251/1406), pancreas of a patient with Fabry's disease (Ref. 1407), hamster fibroblasts (Ref. 1408), human (normal) kidney (Ref. 0004/1240/1253), normal human leucocytes (Ref. 1409), mouse kidneys (BALB/c, C57/BL, A strain) (Ref. 1254), human hepatoma tissue (Ref. 1401), Porcine pancreas (Ref. 1255). (Ref. 1250/1252)




161
Manb1-4Galb1-1Cer
GSG1149
Kazuo Nakamura
Download ChemDraw structure file





starfish (Asterina pectinifera) (Ref. 1393)




162
GlcNAcb1-3Galb1-3GalNAca1-4GalNAcb1-4(2aminoethylphosphoryl-6)GlcNAcb1-3Manb1-4GlcCer
GSG1150
Kazuo Nakamura
Download ChemDraw structure file





Pupae of Calliphora vicina (Insecta: Diptera)(Ref. 1490)larvae of the green-bottle fly, Lucilia caesar(Ref. 2060)




163
GlcUb1-3Galb1-3GalNAca1-4GalNAcb1-4(2aminoethylphosphoryl-6)GlcNAcb1-3Manb1-4GlcCer
GSG1151
Kazuo Nakamura
Download ChemDraw structure file





larvae of the green-bottle fly, Lucilia caesar(Ref. 2057)




164
Gala1-6GlcCer
GSG1153
Kazuo Nakamura
Download ChemDraw structure file





Starfish eggs(Ref. 1488)




165
globoside I/cytolipin K
GalNAcb1-3Gala1-4Galb1-4Glcb1-1Cer
GSG1154
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocytes(Ref. 1423/1422/5080), kidney(Ref. 1396), meconium(Ref. 1260), teratocarcinoma cells(Ref. 1400); Human and porcine plasma(Ref. 1257/1411/1412),Tissues of Tay Sachs' disease variant(Ref. 1421); Rat intestine(Ref. 1140) Canine kidney(Ref. 5082)




166
Cytolipin R
GalNAcb1-3Gala1-3Galb1-4Glcb1-1Cer
GSG1155
Kazuo Nakamura
Download ChemDraw structure file





Rat lymphosarcoma (Ref. 1425), rat kidney (Ref. 1453)




167
asialo-GM1 (AM1)
Galb1-3GalNAcb1-4Galb1-4Glcb1-1Cer
GSG1156
Kazuo Nakamura
Download ChemDraw structure file


MALDI-TOFMS
[Spectrum 0001] (T.Taketomi) Method (Ref. 3072)


Epithelial cells of mouse small intestine (Ref. 1427)




168
paragloboside
Galb1-4GalNAcb1-3Galb1-4GlcCer
GSG1157
Kazuo Nakamura
nLc4Cer
Download ChemDraw structure file




Human erythrocytes (Ref. 1428), neutrophils(Ref. 1161); Bovine spleen, erythrocytes (Ref. 1429)




169
GalNAca1-3GalNAcb1-3Gala1-4GalCer
GSG1158
Kazuo Nakamura
Download ChemDraw structure file
Forsman acitive




Hamster fibroblasts(Ref. 1408)




170
L-Fuca1-2Gala1-3Galb1-4GlcCer
GSG1159
Kazuo Nakamura
Download ChemDraw structure file
Blood group H activity




Hog-stomach mucosa(Ref. 1430)




171
GlcNAcb1-2Manb1-3Manb1-4GlcCer
GSG1160
Kazuo Nakamura
Download ChemDraw structure file





fresh-water bivalve, Hyriopsis schlegelii (Ref. 1431)




172
Forssman antigen
GalNAca1-3GalNAcb1-3Gala1-4Galb1-4GlcCer
GSG1161
Kazuo Nakamura
Download ChemDraw structure file
Forssman antigen




(DB144)(Ref. 1423), Sheep blood cells (Ref. 1397); caprine (goat) erythrocyte (Ref. 1433); Human stomach tumor tissues (Ref. 1173/1434); Horse (Ref. 1435); Guinea pig kidney (Ref. 1436); transplanted canine kidney (Ref. 5082)




173
Gala1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1162
Kazuo Nakamura
Download ChemDraw structure file





Erythrocytes and reticulocytes of rabbit (Ref. 1438); Human erythrocyte (Ref. 5126); Bovine erythrocyte (Ref. 1160)




174
galgactosyl-paragloboside
Galb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1163
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocyte membrane (Ref. 5126)




175
H1 glycolipid
Fuca1-2Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1164
Kazuo Nakamura
Download ChemDraw structure file
H1 antigen




Human erythrocytes (Ref. 1439/5216); Bovine erythrocyte membrane (Ref. 1160)




176
Fuca1-2Galb1-3GalNAcb1-4Galb1-4GlcCer
GSG1165
Kazuo Nakamura
Download ChemDraw structure file
Blood group H acitive




rat ascites hepatoma cell, AH 7974F (Ref. 1440)
fucosyltransferase of rat ascites hepatoma cell, AH 7974F (Ref. 1440)



177
Lewis a
Galb1-3(Fuca1-4)GlcNAcb1-3Galb1-4GlcCer
GSG1166
Kazuo Nakamura
Lea
Download ChemDraw structure file
Le a




Human intestine <<>>, adenocarcinoma, erythrocytes <<>>, plasma <<>>
Lea antigen



178
Gala1-4Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1167
Kazuo Nakamura
Download ChemDraw structure file
blood group P1 antigen




Human erythrocyte(Ref. 1441)




179
X-hapten, SSEA-1, Lex
Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcCer
GSG1168
Yasushi Kawakami
Lex-5
Download ChemDraw structure file





Human adenocarcinoma (Ref. 1326/1327), granulocytes(Ref. 1308), kidney(Ref. 1304); Dog intestine(Ref. 1328); Hog gastric mucosa(Ref. 1313)




180
GlcNAcb1-2Manb1-3(Xylb1-2)Manb1-4GlcCer
GSG1169
Kazuo Nakamura
Download ChemDraw structure file





spermatozoa of Hyriopsis schlegelii(Fresh-water bivalves) (Ref. 5134)




181
GalNAcb1-3(Fuca1-2)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1170
Kazuo Nakamura
Download ChemDraw structure file
Blood group active, Aa

TLC/(-)SIMS
[Spectrum 0001] (Ref. 1499)


Human erythrocytes (Ref. 1442/1443); Dog small intestine (Ref. 1444)




182
Gala1-3(Fuca1-2)Galb1-3GlcNAcb1-3Galb1-4GlcCer
GSG1171
Kazuo Nakamura
Download ChemDraw structure file
Blood group B acitive




Pancreas of a patient with Fabry's disease (Ref. 1407)




183
Gala1-3(Fuca1-2)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1172
Kazuo Nakamura
Download ChemDraw structure file
Blood group B1 acitive




Human erythrocyte membrane (Ref. 1160/1439/1446)




184
GalNAca1-3(Fuca1-2)Galb1-3Galb1-4Galb1-4GlcCer
GSG1173
Kazuo Nakamura
Download ChemDraw structure file
Blood group A active (weak)




hog stomach mucosa (Ref. 1447)




185
Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1174
Kazuo Nakamura
Download ChemDraw structure file





Bovine erythrocytes (Ref. 1160)




186
Fuca1-2Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1175
Kazuo Nakamura
Download ChemDraw structure file
Blood group H2




Human erythrocytes (Ref. 1160/1439/5216)




187
GalNAca1-3(Fuca1-2)Galb1-4Galb1-3(Galb1-6)Galb1-4GlcCer
GSG1176
Kazuo Nakamura
Download ChemDraw structure file





Hog gastric mucosa (Ref. 1448)




188
Gala1-3Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1177
Kazuo Nakamura
Download ChemDraw structure file





Bovine erythrocytes(Ref. 1160)




189
GalNAca1-3(Fuca1-2)Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcCer
GSG1178
Kazuo Nakamura
Download ChemDraw structure file





Hog gastric mucosa (Ref. 1449)




190
GalNAca1-3(Fuca1-2)Galb1-4GlcNAc1-3Galb1-4GlcNAc1-3Galb1-4Galb1-4GlcCer
GSG1179
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocytes (Ref. 1442)




191
Fuca1-2Gal1-4(Fuc-)GlcNAc1-3Gal1-4GlcNAc1-3Gal1-4GlcCer
GSG1180
Kazuo Nakamura
Download ChemDraw structure file





Human tumor tissue (Ref. 1450)




192
GalNAca1-3(Fuca1-2)Galb1-4Galb1-3(GalNAca1-3Galb1-6)Galb1-4GlcCer
GSG1181
Kazuo Nakamura
Download ChemDraw structure file





Hog gastric mucosa (Ref. 1451)




193
GalNAca1-3(Fuca1-2)Galb1-3(GalNAca1-3Galb1-6)Galb1-4Galb1-4GlcCer
GSG1182
Kazuo Nakamura
Download ChemDraw structure file





Hog gastric mucosa (Ref. 1451)




194
GalNAca1-3(Fuca1-2)Galb1-4Galb1-3(GalNAcb1-4Galb1-6)Galb1-4GlcCer
GSG1183
Kazuo Nakamura
Download ChemDraw structure file





Hog gastric mucosa (Ref. 1451)




195
Galb1-4(Fuca1-3)GlcNAcb1-4Galb1-3(GlcNAcb1-4Galb1-6)Galb1-4GlcCer
GSG1184
Yasushi Kawakami
Download ChemDraw structure file





Hog gastric mucosa (Ref. 1448)




196
NeuGca2-3Galb1-4GlcCer
GSG1185
Kazuo Nakamura
GM3
Download ChemDraw structure file









197
NeuAca2-3GalCer
GSG1186
Kazuo Nakamura
GM4
Download ChemDraw structure file





(Ref. 1093)Human myelin(Ref. 1132); Human cerebral white matter,8.6%, gray matter, 1.5% and spinal cord, 12.8%; Cat cerebral white matter, 0.8% and spinal cord, 1.1%), not detected in Rabbit; Human cerebrum myelin, 26.6%, spinal cord myelin 25.3%; Cat cerebrum myelin, 1.0%, spinal cor myelin 1.7%(Ref. 1134); Human brain (white matter, 8.6%; gray matter, 1.5%); White matter of Chimpanzee(8.8%), Monkey(9.0%), Chick(10.8%), Bovine, Sheep(0.6%), Pig(0.7%), Rat(less than 0.1%)(Ref. 1133)



Major normal acid, C24:1, C16:0; major hydroxy acid, 24h:0, 24h:1, 23h:0 (Ref. 1132)
198
8-sulfo-NeuGca2-6GlcCer
GSG1188
Kazuo Nakamura
Download ChemDraw structure file

1235cm-1, 810cm-1<1135>




sea urchin (Echinocardium cordatum)<1135>



Fatty acids Normal acid, 15:0(32.5%); hydroxy acid, 24h:0(19.0%), 22h:0(18.0%), 22h:1(15.4%), (Ref. 1135)

LCB t18:0(56.0%), t16:0(16.7%) (Ref. 1135)
199
Methyl-O-8NeuGca2-3Galb1-4Glc
GSG1189
Kazuo Nakamura
Download ChemDraw structure file





starfish Aphelasterias japonica(Ref. 1491)




200
Methyl-O-8NeuGca2-5(methyl-O-8)NeuGca2-3Galb1-4Glc
GSG1190
Kazuo Nakamura
Download ChemDraw structure file





starfish Aphelasterias japonica(Ref. 1491)




201
Arab1-6Galb1-4(Galb1-8)NeuGc2-3Galb1-4GlcCer
GSG1191
Kazuo Nakamura
Download ChemDraw structure file





Star fish (Asterina pectinifera)<1168>




202
NeuGca2-8NeuGca2-3Galb1-4GlcCer
GSG1192
Kazuo Nakamura
GD3
Download ChemDraw structure file









203
NeuAca2-3Galb1-3GalNAcb1-4(NeuAca2-8NeuAca2-8NeuAca2-3)Galb1-4GlcCer
GSG1193
Kazuo Nakamura
GQ1c
Download ChemDraw structure file





Cod fish brain(Ref. 1188)




204
Gala1-3Gala1-4Galb1-4GlcCer
GSG1194
Kazuo Nakamura
Download ChemDraw structure file





Rat small intestine (Ref. 1300); PC12h pheochromocytoma cells(Ref. 1452)




205
Gala1-3Gala1-3Gala1-4Galb1-4GlcCer
GSG1195
Kazuo Nakamura
Download ChemDraw structure file





Rat intestine (Ref. 1300); PC12h pheochromocytoma cells(Ref. 1301)




206
Gala1-3Gala1-3Gala1-3Gala1-4Galb1-4GlcCer
GSG1196
Kazuo Nakamura
Download ChemDraw structure file





Pheochromcytoma cells PC12h(Ref. 1259)




207
SSEA-3 antigen
Galb1-3GalNAcb1-3Gala1-4Galb1-4GlcCer
GSG1197
Kazuo Nakamura
Download ChemDraw structure file





Human kidney (Ref. 1453), teratocarcinoma cells (Ref. 1454/1455); Mouse kidney (Ref. 1231)




208
GalNAcb1-3Gala1-3Gala1-4Galb1-4GlcCer
GSG1198
Kazuo Nakamura
Download ChemDraw structure file





Rat intestine (Ref. 1233); PC12h pheochromocytoma cells (Ref. 1301)




209
GalNAcb1-3Gala1-3Gala1-3Gala1-4Galb1-4GlcCer
GSG1199
Kazuo Nakamura
Download ChemDraw structure file





Rat intestine (Ref. 1233)




210
GalNAcb1-3Gala1-3Gala1-3Gala1-3Gala1-4Galb1-4GlcCer
GSG1200
Kazuo Nakamura
Download ChemDraw structure file





Rat intestine (Ref. 1233)




211
Amino CTH
GlcNAcb1-3Galb1-4GlcCer
GSG1201
Kazuo Nakamura
Download ChemDraw structure file





Human spleen <<>>, erythrocutes (Ref. 1456), neutrophils (Ref. 1241)




212
Galb1-3GlcNAcb1-3Galb1-4GlcCer
GSG1202
Kazuo Nakamura
LM1, iso-LM1
Download ChemDraw structure file





Human spleen <<>>, embryonal carcinoma cells (Ref. 1457), meconium (Ref. 1378)




213
P antigen
GalNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1203
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocytes (Ref. 1271/1458)




214
Galb1-4GlcNAcb1-3(Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1204
Kazuo Nakamura
Download ChemDraw structure file
monoclonal antibody NUH2
oncodevelopmentally regulated antigen




Human colonic adenocarcinoma (Ref. 1459)




215
N-Methylaminoethylphosphonyl-6GlcCer
GSG1205
Kazuo Nakamura
Download ChemDraw structure file





antarctic krill,euphausia superba(Ref. 2038)




216
Gala1-3Galb1-4GlcNAcb1-3(Gala1-3Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3(Gala1-3Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1206
Kazuo Nakamura
Download ChemDraw structure file
Blood group I/i-active




Rabbit erythrocyte membranes (Ref. 1460)




217
GlcNAcb1-4(GalNAcb1-3)Galb1-4GlcCer
GSG1207
Kazuo Nakamura
Download ChemDraw structure file
Presence in undifferentiated murine leukemia cells and dependence on differentiation




Murine leukemia cells (Ref. 1268)




218
GalNAcb1-4(Gala1-3Galb1-4GlcNAcb1-3)Galb1-4GlcCer
GSG1208
Kazuo Nakamura
Download ChemDraw structure file
Presence in undifferentiated murine leukemia cells and dependence on differentiation




Murine leukemia cells (Ref. 1268)




219
Glcb1-1N-(O-linoleoyl)w-hydroxylignoceroyl sphingpsine
GSG1209
Kazuo Nakamura
Download ChemDraw structure file





Epidermis from footpad and dorsal skin of guinea pigs (Ref. 1461)




220
NeuGc2-3GalCer
GSG1210
Kazuo Nakamura
Download ChemDraw structure file





Mouse erythrocytes (Ref. 1462)




221
deacetyl GM3
NeuNH2-3Galb1-4GlcCer
GSG1211
Kazuo Nakamura
Download ChemDraw structure file
strong promoter for epidermal growth factor receptor kinase and as a stimulator for cell growth (Ref. 1463)




A431 cells and B16 melanoma cells (Ref. 1463)




222
NeuGc2-8NeuAc2-3Galb1-4GlcCer
GSG1212
Kazuo Nakamura
Download ChemDraw structure file





Rabbit thymus (Ref. 1172>; Bovine liver, kidney, spleen, thyroid




223
NeuAc2-8NeuGc2-3Galb1-4GlcCer
GSG1213
Kazuo Nakamura
Download ChemDraw structure file





Cat and sheep erythrocytes (Ref. 1464)




224
Ac-O-9NeuAc2-8NeuAc2-3Galb1-4GlcCer
GSG1214
Kazuo Nakamura
Download ChemDraw structure file





Human melanoma (Ref. 1465)




225
Ac-O-9NeuAc2-8NeuAc2-8NeuAc2-3Galb1-4GlcCer
GSG1216
Kazuo Nakamura
9-O-Ac GT3
Download ChemDraw structure file





embrio chicken brain (Ref. 1424)




226
GalNAcb1-4(NeuGc2-3)Galb1-4GlcCer
GSG1217
Kazuo Nakamura
Download ChemDraw structure file
Hanganutziu-Deicher active
Monoclonal antibody (Ref. 1466)








227
Galb1-3GalNAcb1-4(NeuGc2-3)Galb1-4GlcCer
GSG1218
Kazuo Nakamura
Download ChemDraw structure file





spermatozoa of the sea urchin Anthocidaris crassispina (Ref. 1136)




228
Ac-O-9NeuAc2-3Galb1-3GalNAcb1-4(NeuAc2-3)Galb1-4GlcCer
GSG1219
Kazuo Nakamura
Download ChemDraw structure file





Rat erythrocytes (Ref. 1467)




229
Gala1-3Galb1-3GalNAcb1-4(NeuAca2-8NeuAca2-3)Galb1-4GlcCer
GSG1220
Kazuo Nakamura
Download ChemDraw structure file
Monoclonal antibody AA4 (which inhibits binding of IgE to high affinity receptors on rat basophilic leukemia cells) (Ref. 1468).




Rat leukemia cells (Ref. 1468), Rat basophilic leukemia cells (RBL-2H3) (Ref. 1209)




230
Gala1-3Gala1-3Galb1-3GalNAcb1-4(NeuAc2-8NeuAc2-3)Galb1-4GlcCer
GSG1221
Kazuo Nakamura
Download ChemDraw structure file
Monoclonal antibody AA4 (which inhibits binding of IgE to high affinity receptors on rat basophilic leukemia cells) (Ref. 1468).




Rat leukemia cells (Ref. 1468)




231
Gala1-3(Fuca1-2)Galb1-3GalNAcb1-4(NeuAc2-8NeuAc2-3)Galb1-4GlcCer
GSG1222
Kazuo Nakamura
Download ChemDraw structure file





PC 12 pheochromocytoma cells (Ref. 1199)




232
NeuAc2-3Galb1-3GalNAcb1-4(Ac-O-9NeuAc2-8NeuAc2-3)Galb1-4GlcCer
GSG1223
Kazuo Nakamura
Download ChemDraw structure file





Mouse brain(Ref. 1469)




233
Fuca1-2Galb1-3GalNAcb1-4(NeuGc2-3)Galb1-4GlcCer
GSG1224
Kazuo Nakamura
Download ChemDraw structure file









234
N-methylaminoethylphosphonyl-6Gal1-6Gal1-6GalCer
GSG1225
Kazuo Nakamura
Download ChemDraw structure file










235
GalNAc-GM1
GalNAcb1-4Galb1-3GalNAcb1-4(NeuAc2-3)Galb1-4GlcCer
GSG1226
Kazuo Nakamura
Download ChemDraw structure file





Human brain (Ref. 1100)




236
GalNAca1-3GalNAcb1-3Galb1-3GalNAcb1-4(NeuAc2-3)Galb1-4GlcCer
GSG1227
Kazuo Nakamura
Download ChemDraw structure file





liver of the English sole (Parophrys vetulus) (Ref. 1470)




237
NeuAc2-3Galb1-3GalNAcb1-4(NeuGc2-3)Galb1-4GlcCer
GSG1228
Kazuo Nakamura
GD1a (NeuAc/NeuGc)
Download ChemDraw structure file










238
NeuGc2-3Galb1-3GalNAcb1-4(NeuGc2-3)Galb1-4GlcCer
GSG1229
Kazuo Nakamura
GD1a (NeuGc/NeuGc)
Download ChemDraw structure file









239
NeuGc2-3Galb1-3GalNAcb1-4Galb1-4GlcCer
GSG1230
Kazuo Nakamura
Download ChemDraw structure file





Mouse spleen (Ref. 1471)




240
GalNAcb1-4(NeuGc2-3)Galb1-3GalNAcb1-4Galb1-4GlcCer
GSG1231
Kazuo Nakamura
Download ChemDraw structure file





Mouse spleen (Ref. 1193)




241
Galb1-3GalNAcb1-4(NeuGc2-3)Galb1-3GalNAcb1-4Galb1-4GlcCer
GSG1232
Kazuo Nakamura
Download ChemDraw structure file





Mouse spleen (Ref. 1471)




242
GD1a, GD1e
NeuAc2-3Galb1-3(NeuAc2-6)GalNAcb1-4Galb1-4GlcCer
GSG1234
Kazuo Nakamura
Download ChemDraw structure file





Rat ascites hepatoma cells (Ref. 1472/1478); Differentiation-resistant clone of mouse myeloid leukemia cells, M1-R1 (Ref. 1474)




243
NeuAc2-3Galb1-3(NeuAc2-8NeuAc2-6)GalNAcb1-4Galb1-4GlcCer
GSG1235
Kazuo Nakamura
Download ChemDraw structure file









244
NeuAc2-8NeuAc2-3Galb1-3(NeuAc2-6)GalNAcb1-4Galb1-4GlcCer
GSG1236
Kazuo Nakamura
Download ChemDraw structure file









245
NeuAc2-8NeuAc2-3Galb1-3(NeuAc2-8NeuAc2-6)GalNAcb1-4Galb1-4GlcCer
GSG1237
Kazuo Nakamura
Download ChemDraw structure file









246
NeuAc2-6Galb1-4GlcNAcb1-3(Galb1-4GlcNAcb1-6)Galb1-4GlcCer
GSG1238
Kazuo Nakamura
Download ChemDraw structure file





Bovine buttermilk(Ref. 1476)




247
SSEA-4 antigen
NeuAc2-3Galb1-3GalNAcb1-3Gala1-4Galb1-4GlcCer
GSG1239
Kazuo Nakamura
Download ChemDraw structure file
SSEA-4 antigen




Human teratocaricinoma (Ref. 1455/1454); Rat intestine (Ref. 1300)




248
NeuGc2-3Galb1-3GalNAcb1-3Gala1-4Galb1-4GlcCer
GSG1240
Kazuo Nakamura
Download ChemDraw structure file





Roe of striped mullet, Mugil cephalus(Ref. 1477/1478)




249
NeuAc2-8NeuAc2-3Galb1-3GalNAcb1-3Gala1-4Galb1-4GlcCer
GSG1241
Kazuo Nakamura
Download ChemDraw structure file










250
NeuGc2-8NeuGc2-3Galb1-3GalNAcb1-3Gala1-4Galb1-4GlcCer
GSG1242
Kazuo Nakamura
Download ChemDraw structure file





Roe of striped mullet, Mugil cephalus(Ref. 1477)




251
GalNAcb1-4(NeuAc2-3)Galb1-3GlcNAcb1-3Galb1-4GlcCer
GSG1244
Kazuo Nakamura
Download ChemDraw structure file





Human meconium (Ref. 1479)




252
NeuAc2-3Galb1-3Galb1-3GlcNAcb1-3Galb1-4GlcCer
GSG1245
Kazuo Nakamura
Download ChemDraw structure file










253
disialyl Lea
NeuAc2-3Galb1-3(NeuAc2-6)(Fuca1-4)GlcNAcb1-3Galb1-4GlcCer
GSG1246
Kazuo Nakamura
Download ChemDraw structure file





human colonic adenocarcinoma (Ref. 1111)




254
NeuGc2-8NeuGc2-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1247
Kazuo Nakamura
Download ChemDraw structure file





Human gastrointesinal adenocarcinoma and human gastric cancer cell MKN74 (Ref. 1480)




255
NeuAc2-8NeuGc2-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1248
Kazuo Nakamura
Download ChemDraw structure file





Erythrocytes of cat and sheep (Ref. 1464)




256
GalNAcb1-4(NeuAc2-3)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1249
Kazuo Nakamura
Download ChemDraw structure file





Roe of striped mullet, Mugil cephalus(Ref. 1477)




257
NeuGca2-3Galb1-3GalNAcb1-4(NeuAca2-3)Galb1-4GlcCer
GSG1250
Kazuo Nakamura
Download ChemDraw structure file





Bovine thyroid and adrenal gland




258
NeuAc2-3Galb1-4GlcNAcb1-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcCer
GSG1251
Kazuo Nakamura
Download ChemDraw structure file





Chronic myelogenous leukemia cells(Ref. 1481)




259
NeuAc2-3Galb1-4GlcNAcb1-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1252
Kazuo Nakamura
Download ChemDraw structure file










260
NeuAc2-3Galb1-4GlcNAcb1-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1253
Kazuo Nakamura
Download ChemDraw structure file





Human myeloid cells (Ref. 1482)




261
NeuAc2-3Galb1-3GalNAca1-3(Fuca1-2)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1254
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocytes (Ref. 1116)




262
NeuAc2-3Galb1-4GlcNAca1-3(Fuca1-2Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1255
Kazuo Nakamura
Download ChemDraw structure file





human erythrocyte membranes (Ref. 1120)




263
NeuAc2-3Galb1-4GlcNAca1-3(NeuAca2-3Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1256
Kazuo Nakamura
Download ChemDraw structure file





human erythrocytes (Ref. 1107)




264
NeuAc2-3Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3or6(NeuAca2-3Galb1-4GlcNAcb1-6or3)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1257
Kazuo Nakamura
Download ChemDraw structure file





Human colonic adenocarcinoma (Ref. 1459)




265
NeuAc2-3Galb1-4GlcNAcb1-3(NeuAc2-3Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3or6(NeuAca2-3Galb1-4GlcNAcb1-6or3)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1258
Kazuo Nakamura
Download ChemDraw structure file





Human colonic adenocarcinoma (Ref. 1459)




266
NeuAc2-3Galb1-4GlcNAcb1-3(Gala1-3Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1259
Kazuo Nakamura
Download ChemDraw structure file










267
NeuAc2-3Galb1-4GlcNAcb1-3(GalNAcb1-4)Galb1-4GlcCer
GSG1260
Kazuo Nakamura
Download ChemDraw structure file





Roe of striped mullet, Mugil cephalus(Ref. 1477)




268
GalNAcb1-4(NeuAc2-3)Galb1-4GlcNAcb1-3(GalNAcb1-4)Galb1-4GlcCer
GSG1261
Kazuo Nakamura
Download ChemDraw structure file





Roe of striped mullet, Mugil cephalus(Ref. 1477)




269
NeuAc2-3Galb1-3GalNAcb1-4GlcCer
GSG1262
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocytes (Ref. 1090)




270
4,6-O-Linked plasmalopsychosine
GSG1263
Kazuo Nakamura
Download ChemDraw structure file
Enhances p140trk (Trk A) phosphorylation and mitogen-activated protein kinase (MAPK) activity and as a consequence induces neurite outgrowth in PC12 cells. (Ref. 1129)

(+)FAB-MS (NBA and NBA/sodium acetate matrix) , (-)FAB-MS (triethanolamine/15-crown 5 matrix)
[Spectrum 0001], (+)FAB-MS after acid treatment, (+)FAB-MS after acetylation (Ref. 1122)

TLC: Compund B in Fig. , Lane 5
[Chromatogram 0001] (Ref. 1122)
Human brain (white matter). Detected from white matter, cerebellum and brainstem but not from gray matter. (Ref. 1122)




271
(Compound A)
3,4-O-Linked plasmalopsychosine
GSG1264
Kazuo Nakamura
Download ChemDraw structure file
Enhances p140trk (Trk A) phosphorylation and mitogen-activated protein kinase (MAPK) activity and as a consequence induces neurite outgrowth in PC12 cells. (Ref. 1129)

(+)FAB-MS (NBA matrix)
[Spectrum 0001], (+)FAB-MS after acid treatment, (+)FAB-MS after acetylation (Ref. 1122)

Human brain (white matter). Detected from white matter, cerebellum and brainstem but not from gray matter. (Ref. 1122)



Fatty aldehyde:
272
(SGL-II)
3-O-Methyl-galactosylb1-3N-acetylgalactosaminyla1-3[6'-O-(2-aminoethylphosphonyl)galactosyla1-2](2-aminoethylphosphonyl-6)galactosylb1-4glucosylceramide
GSG1265
Kazuo Nakamura
Download ChemDraw structure file
Activate cyclic adenosine 3',5'-monophosphte-dependent protein kinase from rat brain. (Ref. 1126)
1D 1H-NMR (400MHz)
[Spectrum 0001] (Ref. 1125)
(+)FAB-MS
[Spectrum 0002] (Ref. 1125)


Skin of Aplysia kurodai (sea hare) (Ref. 1125)



Fatty acids 16:0(89.8%), 17:0(4.7%), 18:0(2.3%) (Ref. 1125)

LCB d18:1(50.5%), anteiso-d19:1(38.3%) (Ref. 1125)
273
Fuca1-2Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4Glcb1-1Cer
GSG1267
Yasushi Kawakami
Ley-6
Download ChemDraw structure file





Human colonic carcinoma (Ref. 1331), Dog intestine (Ref. 1328)




274
GlcNAcb1-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4Glcb1-1Cer
GSG1268
Kazuo Nakamura
GlcNAc-Lex-5
Download ChemDraw structure file





human cataractous lense (Ref. 1486)




275
Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4Glcb1-1Cer
GSG1269
Yasushi Kawakami
Lex-7
Download ChemDraw structure file





Human erythrocytes (Ref. 1362), granulocytes (Ref. 1222)




276
Fuca1-2Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4Glcb1-1Cer
GSG1270
Yasushi Kawakami
Ley-8
Download ChemDraw structure file





Human colonic caricinoma (Ref. 1363)




277
Galbl-4(Fucal-3)GlcNAcb1-6(Galb1-3)GalNAcbbl-3Galal-4Galbl-4GlcCer
GSG1272
Kazuo Nakamura
globo-Lex-9
Download ChemDraw structure file





mouse kidney (Ref. 1231)




278
Fuca1-2Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcCer
GSG1273
Yasushi Kawakami
trimeric LeY-9
Download ChemDraw structure file





Human colonic carcinoma (Ref. 1363)




279
Fuca1-2Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-3(Fuca1-4)GlcNAcb1-3Galb1-4GlcCer
GSG1274
Yasushi Kawakami
Ley-A-9
Download ChemDraw structure file





Human meconium (Ref. 1379)




280
Galbl-4(Fucal-3)GlcNAcbl-3Galbl-4GlcNAcb1-3Galbl-4GlcNAcbl-3Galbl-4Glcbl-l'Cer
GSG1275
Kazuo Nakamura
Lex-9
Download ChemDraw structure file





human granulocytes (Ref. 1308), human erythrocytes (Ref. 1362)




281
Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcCer
GSG1277
Yasushi Kawakami
Download ChemDraw structure file





Human colonic and liver carcinoma (Ref. 1364)




282
NeuAca2-3Galbl-4(Fucal-3)GlcNAcbl-3Galbl-4(Fucal-3)GlcNAcbl-3Galbl-4GlcNAcbl-3Galb31-4GlcCer
GSG1281
Kazuo Nakamura
X3 ganglioside
Download ChemDraw structure file





human granulocytes (Ref. 1075)




283
NeuAca2-3Galb1-4(Fucal-3)GlcNAcbl-3Galbl-4GlcNAcbl-3Galbl-4(Fucal-3)GlcNAcbl-3Galbl-4GlcCer
GSG1282
Kazuo Nakamura
X3 ganglioside
Download ChemDraw structure file





human granulocytes (Ref. 1075)




284
NeuAca2-3Galbl-4(Fucal-3)GlcNAcb1-3Galbl-4(Fucal-3)GlcNAcbl-3Galb1-4(Fucal-3)GlcNAcbl-3Galbl-4GlcCer
GSG1283
Kazuo Nakamura
X4 ganglioside
Download ChemDraw structure file





human granulocytes (Ref. 1075)




285
NeuAca2-3Galbl-4(Fucal-3)GlcNAcbl-3(Galbl-4(Fucal-3)GlcNAcbl-3)nGalbl-4Glcbl-l'Cer
GSG1284
Kazuo Nakamura
Band 6
Download ChemDraw structure file





Human blood platelets (Ref. 1487)




286
Galb1-3(Fucal-4)GlcNAcb1-3Galb1-4(Fucal-3)GlcNAcb1-3Galb1-4GlcCer
GSG1285
Kazuo Nakamura
Lea-X
Download ChemDraw structure file





Human squamous lung cancer (Ref. 1343)




287
NeuAca2-3Galb1-3(Fuca1-4)GlcNAcb1-3[Galb1-4(Fuca1-3)GlcNAcb1-6]Galb1-4Glcb1-1Cer
GSG1287
Kazuo Nakamura
sLea-Lex
Download ChemDraw structure file





Human rectal adenocarcinoma (Ref. 1031)




288
NeuAcGalGalCer
GSG1288
Kazuo Nakamura
Download ChemDraw structure file





Human brain of Niemann-Pick disease and gargoylism (Ref. 1190)




289
HSO3-8NeuAca2-8NeuAca2-3Galb1-4Glcb1-1Cer
GSG1289
Kazuo Nakamura
Download ChemDraw structure file





Bovine gastric mucosa (Ref. 1191)



Fatty acids 22:1(21.4%), 24:1(16.3%), 16:0(13.9%), 18:0(13.6%) 18h:0(3.9%), 22h:0(9.9%) (Ref. 1191)

LCB d18:1(85.6%), d18:0(5.2%), t18:1(7.8%) (Ref. 1191)
290
NeuAc-Gal-3Gal-3Gal-Cer
GSG1290
Kazuo Nakamura
Download ChemDraw structure file





Human brain (Ref. 1207)




291
NeuAca2-3Galb1-4(Fuca1-3)GlcNAcb1-3Gala1-3Galb1-4Glcb1-1Cer
GSG1291
Kazuo Nakamura
Download ChemDraw structure file





Salmon gill(Ref. 1494)




292
NeuAca2-3Galb1-4(Fuca1-3)GlcNAcb1-3Gala1-3(GalNAcb1-4)Galb1-4Glcb1-1Cer
GSG1292
Kazuo Nakamura
Download ChemDraw structure file





Salmon gill(Ref. 1494)




293
NeuAca2-3GalNAcb1-3Gala1-4Galb1-4Glcb1-1Cer
GSG1293
Kazuo Nakamura
Download ChemDraw structure file




TLC CMW 55:45:10 Ca2+ between GM3 and GM1
Human teratocarcinoma cell line, HT-E(833K) (Ref. 1192)




294
NeuAca2-3Galb1-3GalNAcb1-3Gala1-3Galb1-4Glcb1-1Cer
GSG1294
Kazuo Nakamura
Download ChemDraw structure file





Rat (Sprague-Dawley and a hooded strain (black-white)) small intestine (Ref. 1201)



d18:1-(16-24:0)
d18:1-(16-24:0)
295
NeuAca2-3Galb1-3GalNAcb1-4Galb1-4Glcb1-1Cer
GSG1295
Kazuo Nakamura
cis GM1, GM1b
Download ChemDraw structure file

1D-H(400MHz)(Ref. 1194)
(-)FABMS, comparison with GM1a(Ref. 1194)

TLC with CMW 50:45:10 Ca2+ slightly slower then GM1a (241)
ICR mouse spleen (Ref. 1193), human brain (whole)(Ref. 1194), rat ascite hepatoma cell lines (AH7974F) (Ref. 1195) tumor(Ref. 1089), human erythrocyte(Ref. 1090), rat ascites hepatoma cells (Ref. 1153), tumor(Ref. 1089), human erythrocyte(Ref. 1090), rat ascites hepatoma cells (Ref. 1153)



Fatty acids ICR mouse spleen, 24:1(33%), 16:0(15%) (Ref. 1193).
Human brain, 18:0(81.4%) (Ref. 1194).
24:1(26.4%), 24:0(19.7%) (Ref. 1089)

LCB Human brain, d18:1(7.6%), d20:1(40.0%) (Ref. 1194).
d18:0(57.6%),d18:0(27.6%) (Ref. 1089)
296
Fuca1-2Galb1-3GalNAcb1-4(NeuAca2-3)Galb1-4Glcb1-1Cer
GSG1296
Kazuo Nakamura
Fuc-GM1
Download ChemDraw structure file

400MHz 1D-H
Direct prove MS (Ref. 1097), GC/MS of PMAA (Ref. 1198), (-)FABMS(Ref. 1199), MALDI-TOFMS
[Spectrum 0001] (T.Taketomi) Method (Ref. 3072)


N-2-Acetylaminofluorene-fed Fischer rat liver(Ref. 1196), rat hepatoma HTC and H35 cells, rat liver and hepatocyte (Ref. 1197), Bovine thyroid (Ref. 1198), PC-12 phenochromocytoma cells (Ref. 1199) Bovine liver (Ref. 1095), brain (Ref. 1156); Boar testis (Ref. 1157), pig adipose tissue (Ref. 1158)



Fatty acids Normal acids less than 10% , 16:0(45%), 2-hydroxy acids more than 90% , 16h:0(42%)
24:0(23.4%), 24:1(20.7%) (Ref. 1199)
297
Fuc1-3Gal1-3GalNAc1-4(NeuAc??-3)Gal1-4Glc1-1Cer
GSG1297
Kazuo Nakamura
Download ChemDraw structure file





Pig adipose tissue (Ref. 1204)



Fatty acids 22:0(25%), 24:0(21%)
298
Galactosylfucosyl-GM1
Gala1-3(Fuca1-2)Galb1-3GalNAcb1-4(NeuAca2-3)Galb1-4Glcb1-1Cer
GSG1298
Kazuo Nakamura
Download ChemDraw structure file
Developmental change in rat stomach (251)




N-2-Acetylaminofluorene-fed Fischer rat liver and rat hepatoma (Ref. 1196); Rat stomach (Sprague-Dawley)(Ref. 1200)



Fatty acids Normal 22:0(15.3%), Hydroxy 24h:0(22.9%), 22h:0(12.8%) (Ref. 1200)

LCB d18:1(23.7%), d20:0(55.2%) (Ref. 1200)
299
Fuca1-3GalNAcb1-3Galb1-3GalNAcb1-4(NeuAca2-3)Galb1-4Glcb1-1Cer
GSG1299
Kazuo Nakamura
Download ChemDraw structure file





Salmon kidney and gill (Ref. 1494)




300
Galb1-3GalNAcb1-4GlcNAcb1-3Manb1-4GlcCer
GSG1300
Kazuo Nakamura
Download ChemDraw structure file









301
Galb?Gala?Galb1-3GalNAcb1-4(NeuAca2-3)Galb1-4Glcb1-1Cer
GSG1301
Kazuo Nakamura
Download ChemDraw structure file





Frog muscle




302
Gala1-3Galb1-3Gala1-3Galb1-3GalNAcb1-4(NeuAca2-3)Galb1-4Glcb1-1Cer
GSG1302
Kazuo Nakamura
Download ChemDraw structure file





Fat body of frog (Rana catesbeiana) (Ref. 1482)



Fatty acids C24:0(20%), C16:0(16%) (Ref. 1482)
303
Fuca1-2Galb1-3GalNAcb1-4(NeuAca2-8NeuAca2-3)Galb1-4Glcb1-1Cer
GSG1303
Kazuo Nakamura
Download ChemDraw structure file

400MHz 1d-H(Ref. 1199)
(-)FABMS(Ref. 1199)


PC12 pheochromocytoma cells (Ref. 1199),Pig cerebellum (263), Miniature pig (type Gottingen) nervous tissues (Ref. 1208)



Fatty acids 24:0(21.8%), 22:0(19.4%) (Ref. 1199)
18:0(80.4%), 20:0(16%), d18:1(60%), d20:1(40%) (Ref. 1103)

LCB d18:1(60%), d20:1(40%) (Ref. 1103)
304
Methyl-O-3Galb1-3GalNAca1-3(2aminoethylphosphonyl-6Gala1-2)Galb1-4GlcCer
GSG1304
Kazuo Nakamura
Download ChemDraw structure file





sea hare, Aplysia kurodai(Ref. 2050)




305
NeuAca2-?GlcNAcb1-3Galb1-4Glcb1-1Cer
GSG1306
Kazuo Nakamura
Download ChemDraw structure file





Human lymphocytes, neutrophils (Ref. 1210)




306
NeuAca2-3GalNAcb1-3Galb1-4GlcNAcb1-3Galb1-4Glcb1-1Cer
GSG1308
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocytes (Ref. 1214)




307
Galb1-3(NeuAca2-6)GlcNAcb1-3Galb1-4Glcb1-1Cer
GSG1309
Kazuo Nakamura
Download ChemDraw structure file





Human meconium (Ref. 1215), colorectal carcinoma (Ref. 1216), lung (Ref. 1217)




308
NeuAca2-3Galb1-3(Fuca1-4)GlcNAcb1-3Galb1-4Glcb1-1Cer
GSG1310
Kazuo Nakamura
Download ChemDraw structure file





Human gastrrointestinal tumor (Ref. 1218), liver metastases of pancreatic adenocarcinoma (Ref. 1219/1220), lung (Ref. 1217)




309
NeuAca2-3Galb1-4GlcNAcb1-3(Fuca1-2Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4Glcb1-1Cer
GSG1312
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocytes(Ref. 1225/1226)




310
NeuAca2-3Galb1-4GlcNAcb1-3(Gala1-3(Fuca1-2)Galb1-4GlcNAcb6)Galb1-4GlcNAcb1-3Galb1-4Glcb1-1Cer
GSG1313
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocytes(Ref. 1226)




311
NeuAca2-3Galb1-4GlcNAcb1-3(GlcNAca1-3(Fuca1-2)Galb1-4GlcNAcb6)Galb1-4GlcNAcb1-3Galb1-4Glcb1-1Cer
GSG1314
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocytes(Ref. 1226)




312
NeuAca2-8NeuAca2-3Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4Glcb1-1Cer
GSG1315
Kazuo Nakamura
Download ChemDraw structure file





Adult bovine nasal cartilage(Ref. 1227)




313
NeuAca2-3Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4Glcb1-1Cer
GSG1316
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocytes(Ref. 1228); Rabbit skeltal muscle(Ref. 1229)




314
HSO3-?NeuGca2-6Glcb1-8NeuGca2-6Glcb1-1Cer
GSG1317
Kazuo Nakamura
Download ChemDraw structure file





Echinocardium cordatum gonads(Ref. 1205)




315
NeuGca2-6Glcb1-8NeuGca2-6Glcb1-1Cer
GSG1318
Kazuo Nakamura
Download ChemDraw structure file





Echinocardium cordatum gonads(Ref. 1205)




316
Ara?1-3Gal?1-3Gal?1-4NeuAca2-?Galb1-4Glcb1-1Cer
GSG1319
Kazuo Nakamura
Download ChemDraw structure file





Hepatopancreas of starfish Patiria pectinifera(Ref. 1026)




317
Ara?1-6Gal?1-3Gal?1-4NeuAca2-?Galb1-4Glcb1-1Cer
GSG1320
Kazuo Nakamura
Download ChemDraw structure file





Hepatopancreas of starfish Patiria pectinifera(Ref. 1026)




318
Ara?1-6Gal?1-3(m8)NeuGca2-3Galb1-4Glcb1-1Cer
GSG1321
Kazuo Nakamura
Download ChemDraw structure file





Starfish Asterina pectinifera (whole tissue)(Ref. 1247/1248/1249)




319
Ara?1-6Gal?1-3NeuGca2-3Galb1-4Glcb1-1Cer
GSG1322
Kazuo Nakamura
Download ChemDraw structure file





Starfish Asterina pectinifera (whole tissue) (Ref. 1247/1248/1249)




320
Ara?1-6Gal?1-3(Gal?1-6)NeuGca2-3Galb1-4Glcb1-1Cer
GSG1323
Kazuo Nakamura
Download ChemDraw structure file





Starfish Asterina pectinifera (whole tissue)(Ref. 1248)




321
HSO3-3Gal?1-4Galb1-4GlcCer
GSG1327
Kazuo Nakamura
Download ChemDraw structure file





Porcine gastric mucosa(Ref. 1246)




322
Gala1-4Galb1-4GlcCer
GSG1328
Kazuo Nakamura
Download ChemDraw structure file
Pk blood group activity(Ref. 1496)




Tissues of Fabry's disease(Ref. 1250/1256), most external tissues (Ref. 1257/1258). Normal human Kidney tissue, Fabry's disease patient kidney tissue. (Ref. 5081) Human erythrocyte and hamster fibloblast. (Ref. 5080)




323
GlcNAcb1-3Gala1-4Galb1-4GlcCer
GSG1330
Kazuo Nakamura
Download ChemDraw structure file





Human meconium(Ref. 1260)




324
Isoglobotriglycosylceramide
Gala1-3Galb1-4GlcCer
GSG1331
Kazuo Nakamura
Download ChemDraw structure file





Rat intestine(Ref. 1201), spleen(Ref. 1261), Rat spleen microsome (Ref. 5087)




325
asialo-GM2, GA2, Tay-Sachs globoside
GalNAcb1-4Galb1-4GlcCer
GSG1332
Kazuo Nakamura
Download ChemDraw structure file





Guinea pig erythrocytes (Ref. 1262/1263); Tissue of Tay Sachs' disease (Ref. 1137/1264/1265/1266/1267)




326
GalNAc?1-4(HSO3-3)Gal?1-4GlcCer
GSG1333
Kazuo Nakamura
Download ChemDraw structure file





Rat kidney<<>>




327
Glcb1-4GlcCer
GSG1334
Kazuo Nakamura
Download ChemDraw structure file









328
GlcNAcb1-3(GalNAcb1-4)Galb1-4GlcCer
GSG1335
Kazuo Nakamura
Download ChemDraw structure file





Murine leukemia cells M1(Ref. 1268)




329
SO3-6GlcNAcb1-3Galb1-4GlcCer
GSG1336
Kazuo Nakamura
III6SO3-Lc3Cer
Download ChemDraw structure file





Hog gastric mucosa(Ref. 1269)




330
Para-Forssman x3b
GalNAcb1-3GalNAcb1-3Gala1-4Galb1-4GlcCer
GSG1338
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocytes(Ref. 1270/1271)




331
Branched Forssman
GalNAca1-3GalNAcb1-3(Galb1-3GalNAcb1-4)Gala1-4Galb1-4GlcCer
GSG1339
Kazuo Nakamura
Download ChemDraw structure file





Dog gastric mucosa(Ref. 1272)




332
HSO3-3Galb1-3GalNAcb1-4Galb1-4GlcCer
GSG1342
Kazuo Nakamura
Download ChemDraw structure file





Mouse small intestine(Ref. 1273/1202); Rat kidney(Ref. 1274)




333
Glcb1-6GlcCer
GSG1343
Kazuo Nakamura
Download ChemDraw structure file









334
Gala1-3Galb1-4GlcNAcb1-3(GalNAcb1-4)Galb1-4GlcCer
GSG1345
Kazuo Nakamura
II3GalNAcb, IV3Gala-nLc4Cer
Download ChemDraw structure file





Murine leukimia cells M1(Ref. 1275)




335
HSO3-3GlcUb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1346
Kazuo Nakamura
Download ChemDraw structure file





Human cauda equina tissure(Ref. 1276), Human peripheral nerve(Ref. 1277)




336
Galb1-4(HSO3-6)GlcNAcb1-3Galb1-4GlcCer
GSG1347
Kazuo Nakamura
Download ChemDraw structure file





Hog gastric mucosa (Ref. 1278)




337
Galb1-4GlcNAcb1-3Galb1-3GlcNAcb1-3Galb1-4GlcCer
GSG1348
Kazuo Nakamura
VI3(Galb1-4GlcNAcb)-Lc4Cer
Download ChemDraw structure file





Human meconium (Ref. 1378/1379)




338
SO3-3GlcUb1-3Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1349
Kazuo Nakamura
Download ChemDraw structure file





Human cauda equina tissue(Ref. 1276)




339
Gala1-3Galb1-4GlcNAcb1-3(Gala1-3Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1350
Kazuo Nakamura
Download ChemDraw structure file





Rabbit erythrocyte (Ref. 1380)




340
Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1351
Kazuo Nakamura
Download ChemDraw structure file





Human granulocytes (Ref. 1381)




341
Fuca1-1Cer
GSG1352
Kazuo Nakamura
Download ChemDraw structure file





Human colon carcinoma (Ref. 1382)




342
Fuca1-2Galb1-4GlcCer
GSG1353
Kazuo Nakamura
Download ChemDraw structure file





Rat intestine (Ref. 1383), murine B cell hybridomas (Ref. 1384)




343
GalNAca1-3(Fuca1-2)Galb1-4GlcCer
GSG1354
Yasushi Kawakami
Download ChemDraw structure file





Rat small intestine (Ref. 1310)




344
9-O-Acetyl-NeuAca2-8NeuAca2-3Galb1-3GalNAcb1-4Galb1-4GlcCer
GSG1355
Yasushi Kawakami
9-O-Acetyl GD1b
Download ChemDraw structure file
Recogonized by serum antibodies in Guillain-Barre syndrome(Ref. 1492)




bovine brain (Ref. 1492)




345
Gala1-3(Fuca1-2)Galb1-4GlcCer
GSG1356
Yasushi Kawakami
Download ChemDraw structure file





Rat large intestine (Ref. 1319)




346
Fuca1-2Gala1-3Gala1-4Galb1-4GlcCer
GSG1357
Yasushi Kawakami
Download ChemDraw structure file





Rat intestine (Ref. 1300);PC 12h pheochromocytoma cells(Ref. 1301)




347 No image
GalNAca1-3(Fuca1-2)Gal?1-3Gal?1-4GlcCer
GSG1358
Yasushi Kawakami





Hog gastric mucosa (Ref. 1313)




348
Fuca1-cGalNAcb1-3Gala1-4Galb1-4GlcCer
GSG1359
Yasushi Kawakami
Download ChemDraw structure file





Human teratocarcinoma (Ref. 1192)




349
Fuca1-2Galb1-3GalNAcb1-3Gala1-4Galb1-4GlcCer
GSG1360
Yasushi Kawakami
Download ChemDraw structure file





Human mammary gland (Ref. 1315), erythrocytes (Ref. 1316), meconium (Ref. 1260), teratocarcinoma cells (Ref. 1303)




350
GalNAca1-3(Fuca1-2)Galb1-3GalNAcb1-3Gala1-4Galb1-4GlcCer
GSG1361
Yasushi Kawakami
Download ChemDraw structure file





Human kidney (Ref. 1317), erythrocytes (Ref. 1318)




351
GalNAca1-3GalNAcb1-3(Fuca1-2Galb1-3GalNAcb1-4)Gala1-4Galb1-4GlcCer
GSG1362
Yasushi Kawakami
Download ChemDraw structure file
Forsmann active, blood group A and H active




Dog gastric mucosa (Ref. 1319)




352
Galb1-3(Galb1-4(Fuca1-3)GlcNAcb1-6)GalNAcb1-3Gala1-4Galb1-4GlcCer
GSG1363
Yasushi Kawakami
Download ChemDraw structure file





Mouse kidney (Ref. 1305)




353
Gala1-3(Fuca1-2)Galb1-3GalNAcb1-3Gala1-3Galb1-4GlcCer
GSG1364
Yasushi Kawakami
Download ChemDraw structure file





Rat gastric mucosa (Ref. 1320)




354
Gala1-3(Fuca1-2)Galb1-3GalNAcb1-4Galb1-4GlcCer
GSG1365
Yasushi Kawakami
Download ChemDraw structure file





Rat gastric mucosa (Ref. 1320), bone marrow, spleen, thymus, ascites hepatoma cells (AH7974F) (Ref. 1322)




355
GalNAca1-3(Fuca1-2)Galb1-4GlcNAcb1-3GalCer
GSG1368
Yasushi Kawakami
Download ChemDraw structure file
Blood group A active




Human erythrocytes (Ref. 1334), pancreas (Ref. 1335), lung (Ref. 1336); Dog intestine (Ref. 1337)




356
Galb1-3GalNAca1-3(Fuca1-2)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1369
Yasushi Kawakami
Download ChemDraw structure file
Blood group A active




Human erythrocytes (Ref. 1116)




357
Gala1-3(Fuca1-2)Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcCer
GSG1370
Yasushi Kawakami
Download ChemDraw structure file





Rabbit intestine (Ref. 1339). Human gastric carcinoma (Ref. 1479). Rat large intestine (Ref. 1341)




358
Galb1-3(Fuca1-4)GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1371
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes (Ref. 1324)




359
Gala1-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcCer
GSG1372
Yasushi Kawakami
Gala1-3Lex
Download ChemDraw structure file





pig kidney(Ref. 1493)




360
Fuca1-2Galb1-3GalNAca1-3(Fuca1-2)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1373
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes (Ref. 1344)




361
GalNAca1-3(Fuca1-2)Galb1-3GalNAca1-3(Fuca1-2)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1374
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes (Ref. 1334)




362
Fuca1-2Galb1-3GlcNAcb1-3Galb1-4GlcCer
GSG1375
Yasushi Kawakami
Download ChemDraw structure file





Human small intestine(Ref. 1346),pancreas(Ref. 1347),meconium(Ref. 1307);Rat intenstine(Ref. 1300)




363
Fuca1-2Galb1-3(Fuca1-4)GlcNAcb1-3Galb1-4GlcCer
GSG1376
Yasushi Kawakami
Download ChemDraw structure file





Human intestine(Ref. 1328/1335/1346/1352), erythrocytes(Ref. 1353)




364
GalNAca1-3(Fuca1-2)Galb1-3GlcNAcb1-3Galb1-4GlcCer
GSG1377
Yasushi Kawakami
Download ChemDraw structure file





Rat intestine(Ref. 1310); Human pancreas(Ref. 1335), erythrocytes(Ref. 1354), plasma(Ref. 1355)




365
Fuca1-2Galb1-4GlcNAcb1-3Galb1-3GlcNAcb1-3Galb1-4GlcCer
GSG1378
Yasushi Kawakami
Download ChemDraw structure file





Human meconium(Ref. 1307)




366
Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-3GlcNAcb1-4Galb1-4GlcCer
GSG1379
Yasushi Kawakami
Download ChemDraw structure file





Human meconium(Ref. 1307)




367
GalNAca1-3(Fuca1-2)Galb1-3(Fuca1-4)GlcNAcb1-3Galb1-4GlcCer
GSG1380
Yasushi Kawakami
Download ChemDraw structure file





Human intestine(Ref. 1328/1335/1346),erythrocytes(Ref. 1354)




368
Gala1-3(Fuca1-2)Galb1-3(Fuca1-4)GlcNAcb1-3Galb1-4GlcCer
GSG1381
Yasushi Kawakami
Download ChemDraw structure file





Human intestine(Ref. 1335/1356)




369
Fuca1-2Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-3GlcNAcb1-3Galb1-4GlcCer
GSG1382
Yasushi Kawakami
Download ChemDraw structure file





Human meconium(Ref. 1307)




370
Gala1-3(Fuca1-2)Galb1-3GalNAcb1-3Galb1-4GlcCer
GSG1384
Yasushi Kawakami
Download ChemDraw structure file





Rat granuloma and macrophage(Ref. 1306)




371
GalNAca1-3(Fuca1-2)Galb1-4Galb1-3(GalNAca1-3Galb1-6)Galb1-4Galb1-4GlcCer
GSG1385
Yasushi Kawakami
Download ChemDraw structure file





Hog gastric mucosa(Ref. 1360)




372
Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcCer
GSG1388
Yasushi Kawakami
Download ChemDraw structure file





Human colonic and liver carcinoma(Ref. 1364),granulocytes(Ref. 1308)




373
Gala1-3(Fuca1-2)Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1389
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes(Ref. 1325)




374
GalNAca1-3(Fuca1-2)Galb1-4JB3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1390
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes(Ref. 1333)




375
Fuca1-2Galb1-4GlcNAcb1-3(Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1392
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes(Ref. 1309)




376
Fuca1-2Galb1-4GlcNAcb1-3(Fuca1-2Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1393
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes(Ref. 1333/1361/1365)




377
GalNAca1-3(Fuca1-2)Galb1-3GalNAca1-3(Fuca1-2)Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1394
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes(Ref. 1334)




378
Gala1-3(Fuca1-2)Galb1-4GlcNAcb1-3(Gala1-3(Fuca1-2)Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3GalCer
GSG1395
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes(Ref. 1366)




379
GalNAca1-3(Fuca1-2)Galb1-4GlcNAcb1-3(GalNAca1-3(Fuca1-2)Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1396
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes(Ref. 1333/1334/1367)




380
Fuca1-2Galb1-3GlcNAcb1-3(Fuca1-2Galb1-3GlcNAcb1-6)Galb1-3GlcNAcb1-3Galb1-4GlcCer
GSG1397
Yasushi Kawakami
Download ChemDraw structure file





Rat intestine(Ref. 1368)




381
Fuca1-2Galb1-3GlcNAcb1-3(Fuca1-2Galb1-4GlcNAcb1-6)Galb1-3GlcNAcb1-3Galb1-4GlcCer
GSG1398
Yasushi Kawakami
Download ChemDraw structure file





Rat intestine(Ref. 1368)




382
GalNAca1-3(Fuca1-2)Galb1-3GlcNAcb1-3(GalNAca1-3(Fuca1-2)Galb1-3GlcNAcb1-6)Galb1-3GlcNAcb1-3Galb1-4GlcCer
GSG1399
Yasushi Kawakami
Download ChemDraw structure file





Rat intestine(Ref. 1369)




383
GalNAca1-3(Fuca1-2)Galb1-3GlcNAcb1-3(GlcNAcca1-3(Fuca1-2)Galb1-4GlcNAcb1-6)Galb1-3GlcNAcb1-3Galb1-4GlcCer
GSG1400
Yasushi Kawakami
Download ChemDraw structure file





Rat intestine(Ref. 1369)




384
HSO3-3Gal?1-4Gal?1-4GlcCer
GSG1401
Yasushi Kawakami
Download ChemDraw structure file





Hog stomach mucosa (Ref. 1246)




385
Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1402
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes(Ref. 1362),granulocytes(Ref. 1308)




386
GalNAca1-3(Fuca1-2)Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1403
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes(Ref. 1334)




387
Fuca1-2Galb1-4GlcNAcb1-3Galb1-4GalNAcb3(Fuca1-2Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1405
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes(Ref. 1367)




388
Gala1-3(Fuca1-2)Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3(Gala1-3(Fuca1-2)Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1406
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes(Ref. 1366)




389
GalNAca1-3(Fuca1-2)Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3(GalNAca1-3(Fuca1-2)Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1407
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes(Ref. 1334/1367)




390
Gala1-3(Fuca1-2)Galb1-4GlcNAcb1-3Galb1-4Galb1-4(Gala1-3(Fuca1-2)Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1408
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes(Ref. 1366)




391
Fuca1-2Galb1-4GlcNAcb1-3(Fuca1-2Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1409
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes(Ref. 1370/1371)




392
Kc3(Fuca1-2)Gal?1-4GlcNAc?1-3(Fc2Gal?1-4GlcNAcb1-6)Gal?1-4GlcNAc?1-3Gal?1-4GlcNAc?1-3Gal?1-4GlcNAc?1-3Gal?1-4GlcNAc?1-3Gal?1-4GlcNAc?1-3Gal?1-4GlcNAc?1-3Gal?1-4GlcNAc?1-3Gal?1-4GlcCer
GSG1410
Yasushi Kawakami
Download ChemDraw structure file





Human erythrocytes(Ref. 1372)




393
GalNAca1-3(Fuca1-2)Galb1-4Galb1-3(GlcNAcca1-3Galb1-6)Galb1-4GlcCer
GSG1411
Yasushi Kawakami
Download ChemDraw structure file





Hog gastric mucosa(Ref. 1360)




394
GalNAca1-3(Fuca1-2)Galb1-4Galb1-3(GlcNAcca1-4Galb1-6)Galb1-4GlcCer
GSG1412
Yasushi Kawakami
Download ChemDraw structure file





Hog gastric mucosa(Ref. 1360)




395
GlcNAcca1-3(Fuca1-2)Gal?1-4(GlcNAcca1-3(Fuca1-2)Gal?1-4GlcNAc?1-6)GlcNAc?1-3(GlcNAc?1-4GlcNAc?1-4)Gal?1-4GlcNAc?1-4(GlcNAc?1-4Gal?1-4GlcNAc?1-6)GlcNAc?1-3HC4GlcCer
GSG1413
Yasushi Kawakami
Download ChemDraw structure file





Hog gastric mucosa(Ref. 1373)




396
GlcNAcca1-3(Fuca1-2)Gal?1-4GlcNAc?1-3(GlcNAc?1-4GlcNAc?1-6)Gal?1-4GlcNAc?1-4GlcNAc?1-3(GlcNAc?1-6)Gal?1-4GlcCer
GSG1414
Yasushi Kawakami
Download ChemDraw structure file





Hog gastric mucosa(Ref. 1360)




397
GalNAca1-3(Fuca1-2)Galb1-3GlcNAcb1-3Galb1-4Galb1-4GlcCer
GSG1415
Yasushi Kawakami
Download ChemDraw structure file





Hog gastric mucosa(Ref. 1374)




398
GalNAca1-3(Fuca1-2)Galb1-4GlcNAcb1-3Galb1-4Galb1-4GlcCer
GSG1416
Yasushi Kawakami
Download ChemDraw structure file





Hog gastric mucosa(Ref. 1374)




399
GalNAca1-3(Fuca1-2)Galb1-3/4GlcNAcb1-3(Fuca1-2Galb1-3/4GlcNAcb1-6)Galb1-4GlcNAcb1-3(Galb1-4GlcNAcb1-3/6(Galb1-4GlcNAcb1-3/6)Galb1-4GlcNAcb1-6)Galb1-4Galb1-4GlcCer
GSG1417
Yasushi Kawakami
Download ChemDraw structure file





Hog gastric mucosa(Ref. 1375)




400
GalNAca1-3(Fuca1-2)Galb1-3/4GlcNAcb1-3(Fuca1-2Galb1-3/4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4Galb1-4GlcCer
GSG1418
Yasushi Kawakami
Download ChemDraw structure file





Hog gastric mucosa(Ref. 1376)




401
GalNAca1-3(Fuca1-2)Galb1-3/4GlcNAcb1-3(Fuca1-2Galb1-3/4GlcNAcb1-6)Galb1-4GlcNAcb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1419
Yasushi Kawakami
Download ChemDraw structure file





Hog gastric mucosa(Ref. 1376)




402
GalNAca1-3(Fuca1-2)Galb1-3/4GlcNAcb1-3(Fuca1-2Galb1-3/4GlcNAcb1-6)Galb1-4GlcNAcb1-3(Galb1-4GlcNAcb1-6)Galb1-4Galb1-4GlcCer
GSG1420
Yasushi Kawakami
Download ChemDraw structure file





Hog gastric mucosa(Ref. 1376)




403
GalNAca1-3(Fuca1-2)Galb1-3/4GlcNAcb1-3(Fuca1-2Galb1-3/4GlcNAcb1-6)Galb1-4GlcNAcb1-4GlcNAcb1-3(Galb1-4GlcNAcb1-6) Galb1-4GlcCer
GSG1421
Yasushi Kawakami
Download ChemDraw structure file





Hog gastric mucosa(Ref. 1376)




404
GalNAca1-3(Fuca1-2)Galb1-4Galb1-3(Galb1-6)Galb1-4GlcCer
GSG1422
Yasushi Kawakami
Download ChemDraw structure file





Hog gastric mucosa(Ref. 1377)




405
Fuca1-2Galb1-3/4GlcNAcb1-6(GalNAca1-3(Fuca1-2)Galb1-3/4GlcNAcb1-3)Galb1-4GlcNAcb1-4GlcNAcb1-3/6(GalNAca1-3(Fuca1-2)Galb1-3/4GlcNAcb1-3)(Galb1-4GlcNAcb1-6)(Galb1-4GlcNAcb1-3/6)Galb1-4GlcCer
GSG1424
Yasushi Kawakami
Download ChemDraw structure file





Hog gastric mucosa(Ref. 1378)




406
NeuGca2-3Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4Glcb1-1Cer
GSG1428
Kazuo Nakamura
Download ChemDraw structure file





(Ref. 1223)bovine erythrocyte(Ref. 1224)Marek's disease lymphoma-derived chicken cell line, MSB1(Ref. 1230)




407
Galb1-3(GlcNAcb1-6)GalNAcb1-3Gala1-4Galb1-4GlcCer
GSG1429
Kazuo Nakamura
Download ChemDraw structure file





mouse kidney(Ref. 1231/1232)




408
Galb1-3(Galb1-4GlcNAcb1-6)GalNAcb1-3Gala1-4Galb1-4GlcCer
GSG1430
Kazuo Nakamura
Download ChemDraw structure file





mouse kidney(Ref. 1231)




409
GalNAcb1-3Gala1-3Gala1-3Gala1-3Gala1-3Gala1-4Galb1-4GlcCer
GSG1432
Kazuo Nakamura
Download ChemDraw structure file










410
GalNAcb1-3Gala1-3Gala1-3Gala1-3Gala1-3Gala1-3Gala1-4Galb1-4GlcCer
GSG1433
Kazuo Nakamura
Download ChemDraw structure file





Rat intestine(Ref. 1233)




411
GalNAcb1-3Gala1-3Gala1-3Galb1-4GlcCer
GSG1434
Kazuo Nakamura
Download ChemDraw structure file





Rat intestine(Ref. 1233)




412
Galb1-4GlcNAcb1-3Galb1-4(Fuca1-3)GlcNAcb1-3Galb1-4GlcCer
GSG1435
Kazuo Nakamura
Download ChemDraw structure file
Monoclonal antibody ACFH-18




Human gastrointesinal adenocarcinoma and human gastric cancer cell MKN74 (Ref. 1480)




413
GalNAca1-3Galb1-4GlcNAcb1-3(Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1436
Kazuo Nakamura
Download ChemDraw structure file









414
Fuca1-3GalNAcb1-3Gala1-3Galb1-4GlcNAcb1-3(GalNAcb1-4)Galb1-4GlcCer
GSG1437
Kazuo Nakamura
Download ChemDraw structure file





liver of the English sole (Parophrys vetulus) (Ref. 1481)




415
GalNAca1-3(Fuca1-2)Galb1-4GlcNAcb1-3Galb1-4GlcNAcb1-3Galb1-4Galb1-4GlcCer
GSG1438
Kazuo Nakamura
Download ChemDraw structure file





Human erythrocytes (Ref. 1442)




416
Galb1-4GlcNAcb1-3Galb1-3GalNAcb1-4(NeuGca2-3)Galb1-4GlcCer
GSG1439
Kazuo Nakamura
Download ChemDraw structure file





Rat spleen (Ref. 1234)




417
Gala1-3Galb1-4GlcNAcb1-3Galb1-3GalNAcb1-4(NeuGca2-3)Galb1-4GlcCer
GSG1440
Kazuo Nakamura
Download ChemDraw structure file





Rat spleen(Ref. 1234)




418
NeuAca2-8NeuAca2-3Galb1-3GalNAcb1-4Galb1-4GlcCer
GSG1441
Kazuo Nakamura
(GD1c)
Download ChemDraw structure file





Spontaneous murine thymoma (Ref. 1235)




419
NeuGca2-8NeuGca2-3Galb1-3GalNAcb1-4Galb1-4GlcCer
GSG1442
Kazuo Nakamura
Download ChemDraw structure file





WHT/Ht Mouse thymoma and thymocytes (Ref. 1236)




420
NeuGca2-8NeuAca2-3Galb1-3GalNAcb1-4Galb1-4GlcCer
GSG1443
Kazuo Nakamura
Download ChemDraw structure file





WHT/Ht mouse thymoma and thymocytes(Ref. 1236)




421
NeuAca2-8NeuGca2-3Galb1-3GalNAcb1-4Galb1-4GlcCer
GSG1444
Kazuo Nakamura
Download ChemDraw structure file





WHT/Ht Mouse thymoma and thymocytes (Ref. 1236)




422
NeuAca2-3Galb1-4GlcNAcb1-3(NeuAca2-3Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3(NeuAca2-3Galb1-4GlcNAcb1-6)Galb1-4GlcNAcb1-3Galb1-4GlcCer
GSG1446
Kazuo Nakamura
Download ChemDraw structure file





Human colonic adenocarcinoma (Ref. 1459)




423
Glucosylb-N-(w-O-acyl)-acylsphingosine
GSG1447
Kazuo Nakamura
Download ChemDraw structure file
Epidermosides are markers for keratinocytes (Ref. 1484)
1H NMR (500MHz) (Ref. 1484)
(-)FAB-MS (Ref. 1484)


Cultured human keratinocytes (Ref. 1484)



Fatty acids 14:1(21.9%), 16:0(4.0%), 16:1(22.1%), 18:0(1.7%), 18:1(31.9%), 18:2(18.4%)
w-hydroxy fatty acid 30h:0, 30h:1, 32h:1, 34h:1 (Ref. 1484)
d18:1 (Ref. 1484)
424
GalNAcb1-4(NeuAca2-3)Galb1-4GlcNAcb1-6(GalNaca1-3GalNAcb1-3Gala1-3)Galb1-4GlcCer
GSG1448
Kazuo Nakamura
Download ChemDraw structure file
Forssman active(Ref. 1495)
2D-HOHAHA, 2D-ROESY(Ref. 1495)
Positive MALDI TOF-MS (native and methylated samples)
Negative SIMS (ceramides)(Ref. 1495)


Equine kidney(Ref. 1495)



Fatty Acids C20h:0,C23h:0,C24h:0,C25h:0(Ref. 1495)
LCB hydroxysphinganine(Ref. 1495)
hybrid of isoglobo-, ganglio- and neolacto-series(Ref. 1495)
425 No image
NeuAc2-8NeuAc2-3Galb1-3(NeuAc2-6)GalNAcb1-4(NeuAc2-3)Galb1-4GlcCer
GSG1449
Kazuo Nakamura
GQ1aa


MALDI-TOF(+)(permethylated sample) (Ref. 1497)

TLC (Ref. 1497)
skate (cartilaginous fish), Bathyraja smirnovi (Ref. 1497)




426 No image
NeuAc2-3Galb1-3(NeuAc2-6)GalNAcb1-4(NeuAc2-8NeuAc2-8NeuAc2-3)Galb1-4GlcCer
GSG1450
Kazuo Nakamura
GP1ca
Neuritogenic activity (Ref. 1497)

MALDI-TOF(+)(permethylated sample) (Ref. 1497)

TLC (Ref. 1497)
skate (cartilaginous fish), Bathyraja smirnovi (Ref. 1497)




427 No image
NeuAca2-8NeuAc2-3Galb1-3(NeuAc2-6)GalNAcb1-4(NeuAc2-8NeuAc2-8NeuAc2-3)Galb1-4GlcCer
GSG1451
Kazuo Nakamura
GH1ca


MALDI-TOF(+)(permethylated sample) (Ref. 1497)

TLC (Ref. 1497)
skate (cartilaginous fish), Bathyraja smirnovi (Ref. 1497)




428
Manb1-4Glcb1-1Cer
GSG2001
Mutsumi Sugita
Download ChemDraw structure file

C-M(2:1)




Corbicula sandai(Ref. 2022), Lucilia caesar(Ref. 2023), Hyriopsis schlegelii (Ref. 2024), Meretrix lusoria(Ref. 2025), Euphausia superba (antarctic krill) (Ref. 2064), Macrobrachium nipponense (fresh-water shrimp) (Ref. 2064), Ascaris suum (porcine roundworm) (Ref. 2066)



Fatty acids L.caesar, 16:0(11.5%), br-16:0(1.7%), 18:0(16.2%), br-18:0(2.6%), 19:0(2.5%), 20:0(49.8%), 22:0(15.7%) (Ref. 2023)
Ascaris suum (porcine roundworm) 16:0(4.3%), 18:0(3.3%), 22:0(8.6%), 21h:0(3.1%), 22h:0(9.7%), 23h:0(4.8%), 24h:0(66.2%) (Ref. 2066)

LCB L.caesar, d14:1(84.2%), d16:1(15.8%) (Ref. 2023)
Ascaris suum (porcine roundworm), br-d17:1(37.1%), br-d17:0(62.9%) (Ref. 2066)
429
Mana1-4Manb1-4Glcb1-1Cer
GSG2002
Mutsumi Sugita
Download ChemDraw structure file

C-M(2:1)




Corbicula sandai(fresh-water bivalves)(Ref. 2022/5094)




430
GlcNAcb1-2Mana1-3Manb1-4Glcb1-1Cer
GSG2003
Mutsumi Sugita
Download ChemDraw structure file

C-M(1:1)




Hyriopsis schlegelii(Ref. 2026) Meretrix lusoria(Ref. 2025)



Fatty acids H.schlegelii, 16:0(22.7%), 17:0(8.3%), 18:0(51.8%), 19:0(6.4%), 20:0(8.5%), 21:0(2.3%)

LCB H.schlegelii, d18:1(97%), iso-d18:1(3%)
431
b-2-ACETAMIDE-2-DEOXY-GLUCOSYL(1-2)a-MANNOSYL(1-3)[b-XYLOSYL(1-2)]b-MANNOSYL(1-4)b-GLUCOSYL(1-1)CERAMIDE
GSG2004
Mutsumi Sugita
Download ChemDraw structure file

C-M(1:1)




Hyriopsis schlegelii(Ref. 2027) Meretrix lusoria(Ref. 2025)



Ceramides H.schlegelii, 16:0(20.5%), 17:0(5.3%), 18:0(52.5%), 19:0(6.7%), 20:0(9.8%), 21:0(2.3%). 22:0(2.8%); LCB d18:1(97%), iso-d18:1(3%)
432
b-4-O-METHYLGALACTOSYL(1-3)b-2-ACETAMIDE-2-DEOXY-GALACTOSYL(1-3)a-FUCOSYL(1-4)b-2-ACETAMIDE-2-DEOXY-GLUCOSYL(1-2)a-MANNOSYL(1-3)[a-XYLOSYL(1-2)][2'-AMINOETHYLPHOSPHORYL(-6)]b-MANNOSYL(1-4)b-GLUCOSYL(1-1)CERAMIDE
GSG2005
Mutsumi Sugita
Download ChemDraw structure file

C-M-W(6:4:1)




Corbicula sandai(Ref. 2028)




433
a-MANNOSYL(1-3)[b-XYLOSYL(1-2)]b-MANNOSYL(1-4)b-GLUCOSYL(1-1)CERAMIDE
GSG2006
Mutsumi Sugita
Download ChemDraw structure file

C-M(1:1)




Hyriopsis schlegelii(Ref. 2029)



Fatty acids 14:0(0.4%), 15:0(0.5%), 16:0(12.2%), 17:0(1.7%), 18:0(20.1%), 19:0(7.5%), 20:0(22.8%), 21:0(3.3%), 22:0(12.5%), 23:0(10.5%), 24:0(8.6%) (Ref. 2029)
d17:1(2.5%), d18:1(68.7%), iso-d18:1(5.2%), d19:1(8.0%), iso-d19:1(3.0%), anteiso-d19:1(12.6%) (Ref. 2029)
434
a-3-O-METHYLFUCOSYL(1-2)b-3-O-METHYLXYLOSYL(1-4)[a-3-O-METHYL-2-ACETAMIDE-2-DEOXY-GALACTOSYL(1-3)]a-FUCOSYL(1-4)b-2-ACETAMIDE-2-DEOXY-GLUCOSYL(1-2)a-MANNOSYL(1-3)[b-XYLOSYL(1-2)]b-MANNOSYL(1-4)b-GLUCOSYL(1-1)CERAMIDE
GSG2007
Mutsumi Sugita
Download ChemDraw structure file

C-M(1:1)
Proton (Ref. 2030)



Hyriopsis schlegelii(Ref. 2030) Meretrix lusoria(Ref. 2025)



Fatty acids 14:0(1.0%), 15:0(3.5%), 16:0(23.2%), 17:0(5.3%), 18:0(53.7%), 19:0(6.4%), 20:0(6.5%), 21:0(1.1%)
d18:1(96.8%), iso-d18:1(3.2%)
435
b-4-O-METHYLGLUCURONYL(1-4)[a-3-O-METHYL-2-ACETAMIDE-2-DEOXY-GALACTOSYL(1-3)]a-FUCOSYL(1-4)b-2-ACETAMIDE-2-DEOXY-GLUCOSYL(1-2)a-MANNOSYL(1-3)[ bXYLOYL(1-2)]b-MANNOSYL(1-4)b-GLUCOSYL(1-1)CERAMIDE
GSG2008
Mutsumi Sugita
Download ChemDraw structure file
Immunohistochemical studies indicated the existence on the cell surface of Hyriopsis spermatozoa.Specific distribution may provide clues to understanding of the molecular basis of the recognition between the spermatozoa and eggs in fertiligation.(Ref. 0032)
C-M-W(6:4:1), water
Proton(Ref. 2031)



Hyriopsis schlegelii(Ref. 2031) Meretrix lusoria(Ref. 2025)



Fatty acids 14:0(0.6%), 15:0(0.4%), 16:0(18.0%), 17:0(5.1%), 18:0(41.3%), 19:0(3.5%), 20:0(6.0%), 21:0(2.6%), 22:0(13.1%), 23:0(3.6%), 24:0(4.7%)
d18:1(97.2%), iso-d18:1(2.8%)
436
b-4-METHYLGALACTOSYL(1-3)b-2-ACETAMIDE-2-DEOXY-GALACTOSYL(1-3)aFUCOSYL(1-4)b-2-ACETAMIDE-2-DEOXY-GLUCOSYL(1-2)a-MANNOSYL(1-3)[a-XYLOSYL(1-2)bMANNOSYL(1-4)b-GLUCOSYL(1-1)CERAMIDE
GSG2009
Mutsumi Sugita
Download ChemDraw structure file

C-M-W(6:4:1), water
Proton



Corbicula sandai(Ref. 2033)




437
b-MANNOSYL(1-2)b-MANNOSYL(1-1)CERAMIDE
GSG2010
Mutsumi Sugita
Download ChemDraw structure file

C-M(2:1)




Hyriopsis schlegelii(Ref. 2024)




438
a-MANNOSYL(1-3)b-MANNOSYL(1-2)b-MANNOSYL(1-1)CERAMIDE
GSG2011
Mutsumi Sugita
Download ChemDraw structure file

C-M(2:1)




Hyriopsis schlegelii(Ref. 2024)




439
a-MANNOSYL(1-3)b-MANNOSYL(1-4)b-GLUCOSYL(1-1)CERAMIDE
GSG2012
Mutsumi Sugita
Download ChemDraw structure file

C-M(2:1)




Hyriopsis schlegelii(Ref. 2029/2024) Meretrix lusoria(Ref. 2025)




440
a-MANNOSYL(1-3)[b-GALACTOSYL(1-2)]b-MANNOSYL(1-4)b-GLUCOSYL(1-1)CERAMIDE
GSG2013
Mutsumi Sugita
Download ChemDraw structure file

C-M(1:1), C-M-W(6:4:1)




Hyriopsis schlegelii (ova) (Ref. 2035)




441
a-GALACTOSYL(1-3)b-MANNOSYL(1-4)b-GLUCOSYL(1-1)CERAMIDE
GSG2014
Mutsumi Sugita
Download ChemDraw structure file

C-M(2:1)




Meretrix lusoria(Ref. 2025)




442
ARABINOSYL(1-6)b-GALACTOSYL[b-GALACTOSYL(1-8)]N-GLYCOLYLNEURAMINYL(2-3)b-GALACTOSYL(1-4)b-GLUCOSYL(1-1)CERAMIDE
GSG2015
Mutsumi Sugita
Download ChemDraw structure file

C-M-W(30:60:8), Folch supernatant
1640,1540cm-1(AMIDE LINKAGE), 1000-1100cm-1(ALCOHOLIC OH) (Ref. 2036)




Asterina pectinifera(Ref. 2036)



Fatty acids 14:0(2.0%), 16:0(6.0%), 17:0(1.2%), 18:0(2.8%), 19:0(0.6%), 20:0(1.2%), 21:0(2.8%), 22:0(47.8%), 23:0(24.5%), 24:0(11.1%)
iso-t16:0(7.2%), t16:0(15.3%), iso-t17:0(28.8%), anteiso-t17:0(13.4%), t17:0(5.3%), iso-t18:0(16.1%), anteiso-t18:0(5.8%), t18:0(8.1%)
443
b-ARABINOSYL(1-6)b-GALACTOSYL(1-4)8-O-METHYL-N-GLYCOLYLNEURAMINYL(2-3)b-GALACTOSYL(1-4)b-GLUCOSYL(1-1)CERAMIDE
GSG2016
Mutsumi Sugita
Download ChemDraw structure file

C-M-W(30:60:8), Folch supernatant




Asterina pectinifera(Ref. 2037), Star fish (Asterina pectinifera)<1168>




444
b-ARABINOSYL(1-6)b-GALACTOSYL(1-4)N-GLYCOLYLNEURAMINYL(2-3)b-GALACTOSYL (1-4)b-GLUCOSYL(1-1)CERAMIDE
GSG2017
Mutsumi Sugita
Download ChemDraw structure file

C-M-W(30:60:8), Folch supernatant




Asterina pectinifera(Ref. 2037), Star fish (Asterina pectinifera)<1168>




445
GlcNAcb1-3Manb1-4Glcb1-1ceramide
GSG2018
Mutsumi Sugita
Download ChemDraw structure file

C-M(1:1)
1540,1645cm-1(AMIDE LINKAGE), 3300cm-1(FREE OH) (Ref. 2023)




Lucilia caesar(Ref. 2023), Macrobrachium nipponense (fresh-water shrimp) (Ref. 2065), Euphausia superba (antarctic krill) (Ref. 2065), Ascaris suum (porcine roundworm) (Ref. 2066)



Fatty acids Lucilia caesar, 16:0(14.2%), br-16:0(1.1%), 18:0(18.6%), br-18:0(2.4%), 19:0(4.9%), 20:0(41.2%), 22:0(17.6%) (Ref. 2023)
Macrobrachium nipponense (fresh-water shrimp) 16:0(5.1%), 18:0(3.8%), 22:0(11.0%), 21h:0(1.9%), 22h:0(6.0%), 23h:0(3.8%), 24h:0(68.4%) (Ref. 2065)
Ascaris suum(porcine roundworm) 16:0(5.1%), 18:0(3.8%), 22:0(11.0%), 21h:0(1.9%), 22h:0(6.0%), 23h:0(3.8%), 24h:0(68.4%) (Ref. 2066)

LCB Lucilia caesar, d14:1(83.4%), d16:1(16.6%) (Ref. 2023)
Macrobrachium nipponense (fresh-water shrimp) br-d17:1(32.8%), br-d17:0(67.2%) (Ref. 2065)
446
b-2-ACETAMIDE-2-DEOXY-GALACTOSYL(1-4)b-2-ACETAMIDE-2-DEOXY-GLUCOSYL(1-3) b-MANNOSYL(1-4)b-GLUCOSYL(1-1)CERAMIDE
GSG2019
Mutsumi Sugita
Download ChemDraw structure file

C-M(1:1)
1540,1645cm-1(AMIDE LINKAGE), 3300cm-1(FREE OH) (Ref. 2023)




Lucilia caesar (Ref. 2023), Ascaris suum (porcine roundworm) (Ref. 2066)



Fatty acids Lucilia caesar 16:0(9.2%), br-16:0(1.6%), 18:0(13.1%), br-18:0(3.1%), 19:0(3.8%), 20:0(50.7%), 22:0(18.5%) (Ref. 2023)
Ascaris suum 16:0(2.2%), 18:0(1.7%), 22h:0(10.6%), C23h:0(5.8%), C24h:0(79.7%) (Ref. 2066)

LCB Lucilia caesar d14:1(82.3%), d16:1(17.7%) (Ref. 2023)
Ascaris suum br-d17:1(33.6%), br-d17:0(66.4%) (Ref. 2066)
447
a-2-ACETAMIDE-2-DEOXY-GALACTOSYL(1-4)b-2-ACETAMIDE-2-DEOXY-GALACTOSYL(1-4)b-2-ACETAMIDE-2-DEOXY-GLUCOSYL(1-3)b-MANNOSYL(1-4)b-GLUCOSYL(1-1) CERAMIDE
GSG2020
Mutsumi Sugita
Download ChemDraw structure file

C-M(1:1)




Lucilia caesar (Ref. 2038)



Fatty acids 16:0(4.0%), 18:0(15.0%), 19:0(7.0%), 20:0(55.0%), 21:0(3.0%), 22:0(16.0%) (Ref. 2038)

LCB d14:1(82.5%), d16:1(17.5%) (Ref. 2038)
448
GlcUb1-3Galb1-3GalNAca1-4GalNAcb1-4GlcNAcb1-3Manb1-4Glcb1-1ceramide
GSG2021
Mutsumi Sugita
Download ChemDraw structure file





Lucilia caesar (green-bottle fly) (Ref. 2057)



Fatty acids 16:0(6.3%), 18:0(12.4%), 20:0(53.1%), 22:0(23.0%), 24:0(5.2%) (Ref. 2057)

LCB d14:1(81.8%), d16:1(18.2%) (Ref. 2057)
449
GlcUb1-3Galb1-3GalNAca1-4GalNAcb1-4(ethanolamine-P-6)GlcNAcb1-3Manb1-4Glcb1-1ceramide
GSG2022
Mutsumi Sugita
Download ChemDraw structure file





Lucilia caesar (green-bottle fly) (Ref. 2057)



Fatty acids 16:0(6.9%), 18:0(13.3%), 20:0(51.3%), 22:0(22.4%), 24:0(6.1%) (Ref. 2057)

LCB d14:1(80.6%), d16:1(19.4%) (Ref. 2057)
450
GalNAcb1-3GlcNAcb1-3Galb1-3GalNAca1-4GalNAcb1-4GlcNAcb1-3Manb1-4Glcb1-1ceramide
GSG2023
Mutsumi Sugita
Download ChemDraw structure file





Lucilia caesar (green-bottle fly) (Ref. 2058)



Fatty acids 16:0(2.6%), 18:0(18.9%), 19:0(5.1%), 20:0(53.9%), 21:0(3.3%), 22:0(16.2%) (Ref. 2058)

LCB d14:1(70.6%), d16:1(29.4%) (Ref. 2058)
451
Galb1-3GalNAcb1-3GlcNAcb1-3Galb1-3GalNAca1-4GalNAcb1-4GlcNAcb1-3Manb1-4Glcb1-1Cer
GSG2024
Mutsumi Sugita
Download ChemDraw structure file





Lucilia caesar (green-bottle fly) (Ref. 2058)



Fatty acids 16:0(2.1%), 18:0(20.3%), 19:0(4.7%), 20:0(54.6%), 21:0(3.7%), 22:0(14.6%) (Ref. 2058)

LCB d14:1(70.4%), d16:1(29.6%) (Ref. 2058)
452
6'-O-(N-methyl-2-aminoethylphosphonyl)Glcb1-1ceramide
GSG2025
Mutsumi Sugita
Download ChemDraw structure file





Euphausia superba (antarctic krill) (Ref. 2059)



Fatty acids 22:0(3.0%), 22:1(17.4%), 22h:1(37.7%), 24:0(2.0%), 24:1(10.5%), 24h:1(23.8%), unidentified(5.6%) (Ref. 2059)

LCB d14:1(17.4%), br-d18:3(24.3%), d18:3(48.2%), unidentified(10.1%) (Ref. 2059)
453
2'-aminoethylphosphoryl-6GlcNAcb1-3Manb1-4Glcb1-1Ceramide
GSG2026
Mutsumi Sugita
Download ChemDraw structure file





Lucilia caesar (green-bottle fly) (Ref. 2060)



Fatty acids 20:0 (Ref. 2060)

LCB d14:1 (Ref. 2060)
454
GalNAcb1-4(2'-aminoethylphosphoryl-6)GlcNAcb1-3Manb1-4Glcb1-1ceramide
GSG2027
Mutsumi Sugita
Download ChemDraw structure file





Lucilia caesar (green-bottle fly) (Ref. 2060)



Fatty acids 20:0 (Ref. 2060)

LCB d14:1 (Ref. 2060)
455
GalNAca1-4GalNAcb1-4(2'-aminoethylphosphoryl-6GlcNAcb1-3Manb1-4Glcb1-1ceramide
GSG2028
Mutsumi Sugita
Download ChemDraw structure file





Lucilia caesar (green-bottle fly) (Ref. 2060)



Fatty acids 20:0 (Ref. 2060)

LCB d14:1 (Ref. 2060)
456
Galb1-3GalNAca1-4GalNAcb1-4(2'-aminoethylphosphoryl-6)GlcNAcb1-3Manb1-4Glcb1-1ceramide
GSG2029
Mutsumi Sugita
Download ChemDraw structure file





Lucilia caesar (green-bottle fly) (Ref. 2060)



Fatty acids 20:0 (Ref. 2060)

LCB d14:1 (Ref. 2060)
457
GlcNAcb1-3Galb1-3GalNAcla1-4GalNAclb1-4(2'-aminoethylphosphoryl-6)GlcNAclb1-3Manlb1-4Glclb1-1ceramide
GSG2030
Mutsumi Sugita
Download ChemDraw structure file





Lucilia caesar (green-bottle fly) (Ref. 2060)



Fatty acids 20:0 (Ref. 2060)

LCB d14:1 (Ref. 2060)
458
Galb1-6Galb1-1ceramide
GSG2032
Mutsumi Sugita
Download ChemDraw structure file





Pheretima hilgendorfi (earthworm) (Ref. 2061)



Fatty acids C16:0(0.2%), C18:0(1.5%), C19:0(0.2%), C20:0(3.6%), C21:0(1.0%), C22:0(47.8%), C23:0(10.5%), C24:0(35.2%) (Ref. 2061)

LCB br-d18:1(18.8%), d18:1(77.0%), br-d19:1(4.2%) (Ref. 2061)
459
Galb1-6Galb1-6Galb1-1ceramide
GSG2033
Mutsumi Sugita
Download ChemDraw structure file





Pheretima hilgendorfi(earthworm) (Ref. 2061)



Fatty acids C16:0(0.2%), C18:0(1.0%), C19:0(0.7%), C20:0(4.3%), C21:0(1.5%), C22:0(46.9%), C23:0(11.4%), C24:0(34.0%) (Ref. 2061)

LCB br-d18:1(12.6%), d18:1(82.7%), br-d19:1(4.7%) (Ref. 2061)
460
choline-P-6Galb1-6Galb1-1ceramide
GSG2034
Mutsumi Sugita
Download ChemDraw structure file





Pheretima hilgendorfi (earthworm) (Ref. 2062)



Fatty acids 16:0(1.5%), 18:0(5.8%), 20:0(4.9%), 21:0(3.7%), 22:0(56.0%), 23:0(7.1%), 24:0(20.9%) (Ref. 2062)

LCB, br-d18:1(52.5%) , d18:1(18.7%), br-d19:1(28.8%) (Ref. 2062)
461
Choline-P-6Galb1-1ceramide
GSG2036
Mutsumi Sugita
Download ChemDraw structure file

(+)FAB-MS
[Spectrum 0003] (Ref. 1054)

Tylorrhynchus heterochetus (lugworm) (Ref. 2063), Hirudo nipponia (leech) (Ref. 2069)



Fatty acids Tylorrhynchus heterochetus (lugworm) 16:0(82.6%), 17:0(8.5%), 18:0(8.9%) (Ref. 2063)
Hirudo nipponia (leech) 16:0(13.2%), 17:0(5.4%), 18:0(19.1%), 22:0(24.0%), C24:0(31.2%), unknown(7.1%) (Ref. 2069)

LCB Tylorrhynchus heterochetus (lugworm), d18:1(57.8%), d18:2(42.4%) (Ref. 2063)
Hirudo nipponia (leech), br-d18:1(9.6%), d18:1(48.5%), br-d19:1(18.4%), d22:3(23.5%) (Ref. 2069)
462
Gala1-3GalNAcb1-4GlcNAcb1-3Manb1-4Glcb1-1ceramide
GSG2041
Mutsumi Sugita
Download ChemDraw structure file





Ascaris suum (porcine roundworm) (Ref. 2066)



Fatty acids 16:0(3.2%), 18:0(2.1%), C22h:0(12.7%), C23h:0(4.6%), C24h:0(77.4%) (Ref. 2066)

LCB br-d17:1(31.3%), br-d17:0(68.7%) (Ref. 2066)
463
Mana1-4Galb1-6Galb1-1ceramide
GSG2045
Mutsumi Sugita
Download ChemDraw structure file





Pheretima hilgendorfi (earthworm) (Ref. 2067)



Fatty acids 16:0(1.7%), 18:0(4.6%), 20:0(8.3%), 21:0(4.1%), 22:0(49.4%), 23:0(11.3%), 24:0(20.6%); (Ref. 2067)

LCB, br-d18:1(59.6%) , d18:1(14.6%), br-d19:1(25.8%) (Ref. 2067)
464
Gala1-6(Mana1-4)Galb1-6Galb1-1ceramide
GSG2046
Mutsumi Sugita
Download ChemDraw structure file





Pheretima hilgendorfi (earthworm) (Ref. 2067)



Fatty acids 22:0(30.7%), 23:0(27.2%), 24:0(42.1%) (Ref. 2067)

LCB br-d18:1(47.4%), d18:1(23.9%), br-d19:1(28.7%) (Ref. 2067)
465
Choline-P-6Galb1-6Galb1-6Galb1-1ceramide
GSG2047
Mutsumi Sugita
Download ChemDraw structure file

3400, 1620, 1540, 1220, 960cm-1 (Ref. 2068)
500MHz 1H (Ref. 2068)
(+)FAB-MS (Ref. 2068)


Pheretima hilgendorfi (earthworm) (Ref. 2068)



Fatty acids 16:0(1.4%), 18:0(4.4%), 20:0(5.1%), 21:0(4.7%), 22:0(50.8%), 23:0(11.9%), 24:0(21.7%) (Ref. 2068)
LCB, d18:1(19.3%), br-d19:1(25.3%) (Ref. 2068)
466
Choline-P-6Galb1-6Galb1-1ceramide
GSG2048
Mutsumi Sugita
Download ChemDraw structure file

1H NMR (SP0001) (Ref. 1054)
(+)FAB-MS
[Spectrum 0002] (Ref. 1054)

TLC : lane 3
[Chromatogram 0001] (Ref. 1054)
Hirudo nipponia (leech) (Ref. 2069), Pheretima hilgendorfi (earthworm) (Ref. 1054)



Fatty acids 16:0(11.3%), 18:0(11.2%), 22:0(27.3%), 24:0(41.4%), unknown(8.8%) (Ref. 2069)

LCB, d18:1(6.0%), t18:0(24.7%), br-d19:1(13.5%), d19:1(6.8%), br-t19:0(29.5%), d22:3(19.5%) (Ref. 2069)
467
Gala1-6Gala1-6Gala1-6Galb1-1ceramide
GSG2050
Mutsumi Sugita
Download ChemDraw structure file





Hirudo nipponia (leech) (Ref. 2069)



Fatty acids 16:0(8.5%), 18:0(11.2%), 22:0(44.2%), 24:0(27.8%), unknown(8.3%) (Ref. 2069)

LCB br-d18:1(3.4%), d18:1(13.5%), d18:0(5.0%), t18:0(7.1%), br-d19:1(18.5%), d19:1(22.9%), d22:3(29.6%) (Ref. 2069)
468
Gala1-6Gala1-6Galb1-1ceramide
GSG2051
Mutsumi Sugita
Download ChemDraw structure file





Hirudo nipponia (leech) (Ref. 2069)



Fatty acids 16:0(12.1%), 18:0(7.3%), 22:0(34.3%), 24:0(37.5%), unknown(8.7%) (Ref. 2069)

LCB, br-d18:1(4.0%), d18:1(23.8%), d18:0(8.6%) , br-d19:1(43.2%), d19:1(7.8%), d22:3(12.6%) (Ref. 2069)
469
Gala1-6Galb1-1ceramide
GSG2052
Mutsumi Sugita
Download ChemDraw structure file





Hirudo nipponia (leech) (Ref. 2069)



Fatty acids 16:0(15.3%), 18:0(6.2%), 22:0(28.2%), 24:0(42.2%), unknown(8.1%) (Ref. 2069)

LCB br-d18:1(5.2%), d18:1(23.0%), d18:0(6.8%), br-d19:1(51.5%), d19:1(8.5%), d22:3(5.0%) (Ref. 2069)
470
Glca1-4Galb1-6Galb1-1ceramide
GSG2053
Mutsumi Sugita
Download ChemDraw structure file





Pheretima sp.(earthworm) (Ref. 2070)



Fatty acids 20:0(2.4%), 22:0(49.7%), 23:0(5.2%), 24:0(42.7%) (Ref. 2070)

LCB br-d18:1(7.1%), d18:1(92.9%) (Ref. 2070)
471
Glca1-4Galb1-6Galb1-6Galb1-1ceramide
GSG2054
Mutsumi Sugita
Download ChemDraw structure file





Pheretima sp.(earthworm) (Ref. 2070)



Fatty acids 22:0(62.8%), 23:0(4.9%), 24:0(32.3%) (Ref. 2070)

LCB br-d18:1(3.0%), d18:1(97.0%) (Ref. 2070)
472
Glca1-4Galb1-6(Glca1-4)Galb1-6Galb1-1ceramide
GSG2055
Mutsumi Sugita
Download ChemDraw structure file





Pheretima sp.(earthworm) (Ref. 2070)



Fatty acids 18:0(5.4%), 20:0(8.2%), 21:0(4.6%), 22:0(41.4%), 23:0(13.7%), 24:0(26.7%) (Ref. 2070)

LCB br-d18:1(7.3%), d18:1(92.7%) (Ref. 2070)
473
InoMe(1-)-P-ceramide
GSG2056
Mutsumi Sugita
Download ChemDraw structure file





Tylorrhynchus heterochetus (lugworm) (Ref. 2071)



Fatty acids 16h:0(10.0%), 17h:0(9.0%), 18h:0(43.1%), 19h:0(7.6%), 20h:0(7.3%), 21h:0(4.3%), h-C22h:0(6.8%), 23h:0(3.5%), 24h:0(8.4%) (Ref. 2071)

LCB t18:0(100%) (Ref. 2071)
474
Fuc-InoMe(1-)-P-ceramide
GSG2057
Mutsumi Sugita
Download ChemDraw structure file





Tylorrhynchus heterochetus (lugworm) (Ref. 2071)



Fatty acids 16h:0(22.9%), 17h:0(11.5%), 18h:0(45.9%), 19h:0(6.8%), 20h:0(3.7%), 21h:0(1.8%), 22h:0(2.8%), 23h:0(1.4%), 24h:0(3.2%) (Ref. 2071)

LCB t18:0(100%) (Ref. 2071)
475
Ino(1-)-P-ceramide
GSG2058
Mutsumi Sugita
Download ChemDraw structure file





Tylorrhynchus heterochetus (lugworm) (Ref. 2071)



Fatty acids 16:0(50.9%), 17:0(7.5%), 18:0(28.6%), 20:0(5.8%), 22:0(7.2%) (Ref. 2071)

LCB d18:1(81.2%), d18:0(18.8%) (Ref. 2071)
476
Manb1-1ceramide
GSG2059
Mutsumi Sugita
Download ChemDraw structure file





Hyriopsis schlegelii(Ref. 2077)




477
GlcNAcb1-3Galb1-3GalNAca1-4GalNAcb1-4GlcNAcb1-3Manb1-4Glcb1-1ceramide
GSG2060
Mutsumi Sugita
Download ChemDraw structure file





Lucilia caesar (green-bottle fly)(Ref. 2037)




478
Galb1-3GalNAca1-4GalNAcb1-4GlcNAcb1-3Manb1-4Glcb1-1ceramide
GSG2061
Mutsumi Sugita
Download ChemDraw structure file





Lucilia caesar (green-bottle fly)(Ref. 2037)




479
Galb1-4Galb1-1ceramide
GSG2062
Mutsumi Sugita
Download ChemDraw structure file





Hyriopsis schlegelii hepatopancreas(Ref. 2024)




480
Mana1-2Ino(GlcNAca1-4GlcNAca1-6)(1-P-)1-1ceramide
GSG2063
Mutsumi Sugita
Download ChemDraw structure file





Corn seed(Ref. 2078/2079)




481
Man1-2Ino-(1-P)-1ceramide
GSG2064
Mutsumi Sugita
Download ChemDraw structure file





Yeast(Ref. 2080),fungi(Ref. 2081)




482
(Gal, Ara, Man)-GlcNH2-GlcU-Ino-(1-P)-1Ceramide
GSG2065
Mutsumi Sugita
Download ChemDraw structure file





Peanuts(Ref. 2082)




483
Ino-P-Ino-(1-P)-1Ceramide
GSG2066
Mutsumi Sugita
Download ChemDraw structure file





Yeast(Ref. 2083), Fungi(Ref. 2081/2084)




484
Ino-P-Man-Ino-(1-P)-1Cer
GSG2067
Mutsumi Sugita
Download ChemDraw structure file





Yeasr,Fungi(Ref. 2083)




485
(Man, Gal)-Ino-(1-P)-1Ceramide
GSG2068
Mutsumi Sugita
Download ChemDraw structure file





Aspergillus niger(Ref. 2085/2086)




486
(Man, Gal, Glc)-Ino-(1-P)-Ceramide
GSG2069
Mutsumi Sugita
Download ChemDraw structure file





Aspergillus niger(Ref. 2085/2086)




487
(Man2, Gal3)-Ino-(1-P)-1Ceramide
GSG2070
Mutsumi Sugita
Download ChemDraw structure file





Aspergillus niger(Ref. 2085/2086)




488
GlcNAca1-4GlcUa1-2Ino(1-P)-1Cer
GSG2071
Mutsumi Sugita
Download ChemDraw structure file









489
Galb1-4GlcNAca1-4GlcUa1-2Ino(1-P)-1Cer
GSG2072
Mutsumi Sugita
Download ChemDraw structure file





Tabacco(Ref. 2092)




490
Gal1-6Gal1-4GlcNAca1-4GlcUa1-2Ino(1-P)-1Cer
GSG2073
Mutsumi Sugita
Download ChemDraw structure file





Tabacco(Ref. 2093)




491
Ara1-6Gal1-4GlcNAca1-4GlcAa1-2Ins(1-P)-1Cer
GSG2074
Mutsumi Sugita
Download ChemDraw structure file





Tabacco(Ref. 2093)




492
Gal/Ara1-3Gal(Gal/Ara1-6)1-4GlcNAca1-4GlcUa1-2Ino(1-P)-1Cer
GSG2075
Mutsumi Sugita
Download ChemDraw structure file





Tabacco(Ref. 2093)




493
Mana1-3Mana1-2/6Ino(1-P)-1Cer(OH)
GSG2076
Mutsumi Sugita
Download ChemDraw structure file





H. capsulataum(Ref. 2094)




494
Mana1-3(Galb1-6)Mana1-2/6Ino(1-P)-1Cer(OH)
GSG2077
Mutsumi Sugita
Download ChemDraw structure file





H. capsulataum(Ref. 2094)




495
Mana1-3(Galb1-4)Mana1-2/6Ino(1-P)-1Cer(OH)
GSG2078
Mutsumi Sugita
Download ChemDraw structure file





H. capsulataum(Ref. 2094)




496
H2N-CH2-CH2-PO4-6Gal-Cer
GSG2079
Mutsumi Sugita
Download ChemDraw structure file





T, cornutus(Ref. 2095/2096/2097), Monodona labio(marine gastropod)(Ref. 2097)




497
CH3-HN-CH2-CH2-PO4-6Gal-Cer
GSG2080
Mutsumi Sugita
Download ChemDraw structure file





T, cornutus(Ref. 2095/2096/2098)




498
N-acetylneraminyla2-3galactosylb1-4glucosylceramide
GSG3001
Hideharu Ishida
GM3
C55H100N2O21 1125.383 Download ChemDraw structure file
This ganglioside have the immunosuppressive properties of the natural molecules and are useful in probing which elements of ganglioside structure are critical to their biological activity.(Ref. 3002)
Binding specificites of the sialoadhesin family of I-type lectins was examined by employing this ganglioside. (Ref. 3046)
+1.8deg(Ref. 3001)
1D 1H-NMR (Ref. 3001)



Chemical Synthesis
Coupling of a-(trimethylsilyl)ethyl O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside, prepared from 2-(trimethylsilyl)ethyl b-lactoside by selective 3'-O-benzylation, O-bezoylation, and subsequent removal of the benzyl group, with methyl(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-a-D-galacto-2-nonulopyranosid)onate using dimethyl(methylthio)sulfonium triflate as a glycosyl promoterm gave 2-(trimethylsilyl)ethyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside, which was converted, via O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation,
into the a-N-acetylneuraminyl-(2-3')-lactose trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with afforded the b-glycoside, which was converted, via selective of the azide group, coupling with tetradecanoic acid, O-deacylation, and de-esterification, into the title compounds. (Ref. 3001)


Fatty acid C14:0

LCB d18:1
499
N-acetylneraminyla2-3galactosylb1-4glucosylceramide
GSG3002
Hideharu Ishida
GM3
C59H108N2O21 1181.490 Download ChemDraw structure file
This ganglioside have the immunosuppressive properties of the natural molecules and are useful in probing which elements of ganglioside structure are critical to their biological activity.(Ref. 3002)
Binding specificites of the sialoadhesin family of I-type lectins was examined by employing this ganglioside. (Ref. 3046)
+1.8deg(Ref. 3001)
1D 1H-NMR (Ref. 3001)



Chemical Synthesis
Coupling of a-(trimethylsilyl)ethyl O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside, prepared from 2-(trimethylsilyl)ethyl b-lactoside by selective 3'-O-benzylation, O-bezoylation, and subsequent removal of the benzyl group, with methyl(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-a-D-galacto-2-nonulopyranosid)onate using dimethyl(methylthio)sulfonium triflate as a glycosyl promoterm gave 2-(trimethylsilyl)ethyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside, which was converted, via O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation,
into the a-N-acetylneuraminyl-(2-3')-lactose trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with afforded the b-glycoside, which was converted, via selective of the azide group, coupling with octadecanoic acid, O-deacylation, and de-esterification, into the title compounds. (Ref. 3001)


Fatty acid C18:0

LCB d18:1
500
N-acetylneraminyla2-3galactosylb1-4glucosylceramide
GSG3003
Hideharu Ishida
GM3
C65H120N2O21 1265.649 Download ChemDraw structure file
This ganglioside have the immunosuppressive properties of the natural molecules and are useful in probing which elements of ganglioside structure are critical to their biological activity.(Ref. 3002)
Binding specificites of the sialoadhesin family of I-type lectins was examined by employing this ganglioside. (Ref. 3046)
+0.8deg(Ref. 3001)
1D 1H-NMR (Ref. 3001)



Chemical Synthesis
Coupling of a-(trimethylsilyl)ethyl O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside, prepared from 2-(trimethylsilyl)ethyl b-lactoside by selective 3'-O-benzylation, O-bezoylation, and subsequent removal of the benzyl group, with methyl(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-a-D-galacto-2-nonulopyranosid)onate using dimethyl(methylthio)sulfonium triflate as a glycosyl promoterm gave 2-(trimethylsilyl)ethyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside, which was converted,
via O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the a-N-acetylneuraminyl-(2-3')-lactose trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with afforded the b-glycoside, which was converted, via selective of the azide group, coupling with tetracosanoic acid, O-deacylation, and de-esterification, into the title compounds. (Ref. 3001)


Fatty acid C24:0

LCB d18:1
501
N-acetylneraminyla2-3galactosylceramide
GSG3004
Hideharu Ishida
GM4
C49H90N2O16 963.243 Download ChemDraw structure file
This ganglioside have the immunosuppressive properties of the natural molecules and are useful in probing which elements of ganglioside structure are critical to their biological activity.(Ref. 3002)
Binding specificites of the sialoadhesin family of I-type lectins was examined by employing this ganglioside. (Ref. 3046)
+2.5deg(Ref. 3003)
1D 1H-NMR (Ref. 3003)



Chemical Synthesis
The glycosylation of 2-(trimethylsilyl)ethyl 6-O-benzoyl-b-D-galactopyranoside with the methyl a-thioglycoside derivativem derived from methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-S-acetyl-3,5-dideoxy-2-thio-D-glycero-a-D-galacto-2-nonulopyranosonate via selective S-deacetylation and subsequent S-methylation, using dimethyl(methylthio)sulfonium triflate (DMTST) gave the corresponding a-glycosides of Neu5Ac, respectively. Coupling of the trichloroacetimidates, obtained by O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and imidate formation, with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the corresponding b-glycoside, which was converted via selective reduction of the azide group, condensation with tetradecanoic acid, O-deacylation, and hydrolysis of the methyl ester group into the title compound. (Ref. 3003)


Fatty acid C14:0

LCB d18:1
502
N-acetylneraminyla2-3galactosylceramide
GSG3005
Hideharu Ishida
GM4
C53H98N2O16 1019.349 Download ChemDraw structure file
This ganglioside have the immunosuppressive properties of the natural molecules and are useful in probing which elements of ganglioside structure are critical to their biological activity.(Ref. 3002)
Binding specificites of the sialoadhesin family of I-type lectins was examined by employing this ganglioside. (Ref. 3046)
+2.2deg(Ref. 3003)
1D 1H-NMR (Ref. 3003)



Chemical Synthesis
The glycosylation of 2-(trimethylsilyl)ethyl 6-O-benzoyl-b-D-galactopyranoside with the methyl a-thioglycoside derivativem derived from methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-S-acetyl-3,5-dideoxy-2-thio-D-glycero-a-D-galacto-2-nonulopyranosonate via selective S-deacetylation and subsequent S-methylation, using dimethyl(methylthio)sulfonium triflate (DMTST) gave the corresponding a-glycosides of Neu5Ac, respectively. Coupling of the trichloroacetimidates, obtained by O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and imidate formation, with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the corresponding b-glycoside, which was converted via selective reduction of the azide group, condensation with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group into the title compound. (Ref. 3003)


Fatty acid C18:0

LCB d18:1
503
sialyl-lactotetraosylceramide
N-acetylneraminyla2-3galactosylb1-3-N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3006
Hideharu Ishida
C73H131N3O32 1562.822 Download ChemDraw structure file
This ganglioside was the most potent ganglioside bound by Influenza Virus A/PR/8.(Ref. 3032)
This ganglioside gave a negative reaction to a lymphocyte homing receptor, L-selectin (LECAM-1). (Ref. 3035)
This ganglioside was more sensitive to the sialidase of influenza B virus isolates than the corresponding sialyl a2-6gal isomer. (Ref. 3036)
This ganglioside was recognized by the hemagglutinin of human influenza B virus isolates as well as the sorreponding 2-6 isomer. (Ref. 3038)
-6.2deg(Ref. 3004)
1D 1H-NMR (Ref. 3004)



Chemical Synthesis
Methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside, the key glycosyl donor, was prepared, from the 2-(trimethylsilyl)ethyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-6-O- benzoyl-b-D-galactopyranoside, via benzoylation, replacement of the 2-(trimethylsilyl)ethyl group by acetyl, and introduction of the methylthio group with methylthiotrimethylsilane. Coupling of 2-(trimethylsilyl)ethyl 2,3,6,2',4',6'-hexa-O-benzyl- b-D-galactopyranoside, prepared from 2-(trimethylsilyl)ethyl b-D-lactoside via selective 3'-O-(4-methyoxybenzylation), benzylation,
and selective removal of the 4-methyoxybenzyl group, with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimide-D-glucopyranosyl bromide gave a trisaccharide derivative, from which the phthaloyl and O-acetyl groups were removed. N-Acetylation then gave 2-(trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-b-D-galactopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside. Dimethyl(methylthio)sulfonium triflate promoted coupling of the disaccharide donor with the trisaccharide acceptor, prepared by 4,6-O-benzylidenation, gave the corresponding pentasaccharide. This oligosacharide was converted into the corresponding a-trichloroacetimidates which, on coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycosides. Finally, the compound was transformed, via selective reduction of the azide group, condensation with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the final product.(Ref. 3004)


Fatty acid C18:0

LCB d18:1
504
sialyl-neolactotetraosylceramide/sialyl-paragloboside
N-acetylneraminyla2-3galactosylb1-4-N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3007
Hideharu Ishida
C73H131N3O32 1562.822 Download ChemDraw structure file
This ganglioside gave a negative reaction to a lymphocyte homing receptor, L-selectin (LECAM-1). (Ref. 3035)
A new monoclonal antibody directed to this ganglioside was prepared, and which was applied for detection of human gastrointestinal neoplasmas (Ref. 3050)
-3.8deg(Ref. 3004)
1D 1H-NMR (Ref. 3004)



Chemical Synthesis
Methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside, the key glycosyl donor, was prepared, from the 2-(trimethylsilyl)ethyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy -D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-6-O-benzoyl-b-D- galactopyranoside, via benzoylation, replacement of the 2-(trimethylsilyl)ethyl group by acetyl, and introduction of the methylthio group with methylthiotrimethylsilane. Coupling of 2-(trimethylsilyl)ethyl 2,3,6,2',4',6'-hexa-O-benzyl-b-D-galactopyranoside, prepared from 2-(trimethylsilyl)ethyl b-D-lactoside via selective 3'-O-(4-methyoxybenzylation), benzylation, and selective removal of the 4-methyoxybenzyl group, with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimide-D-glucopyranosyl bromide gave a trisaccharide derivative, from which the phthaloyl and O-acetyl groups were removed.
N-Acetylation then gave 2-(trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-b-D-galactopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside. Dimethyl(methylthio)sulfonium triflate promoted coupling of the disaccharide donor with the trisaccharide acceptor, prepared by 4,6-O-benzylidenation, 3-O-(4-methoxybenzylation) and reductive opening of the benzylidene acetal, gave the corresponding pentasaccharide derivatives 16 and 20 in good yields. This oligosacharide was converted into the corresponding a-trichloroacetimidates which, on coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycosides. Finally, the compound was transformed, via selective reduction of the azide group, condensation with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the final product.(Ref. 3004)


Fatty acid C18:0

LCB d18:1
505
sialyl-Lex
N-acetylneraminyla2-3galactosylb1-4(fucosyla1-3)N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3008
Hideharu Ishida
C79H141N3O36 1708.963 Download ChemDraw structure file
This ganglioside was recognized by none of the selectin receptor family. (Ref. 3033)
This ganglioside was weakly recognized by monoclonal antibody AM-3 which raised against a sialomucin from human coloretal carcinoma. (Ref. 3034)
This ganglioside was bound by a lymphocyte homing receptor, L-selectin (LECAM-1) but lower than the sulfatide. (Ref. 3035)
One of the monoclonal antibodies, which raised against this ganglioside, is found to react sellectively to helper memory T cells. (Ref. 3037)
This ganglioside inhibits lung metastasesprduced by i.v. co-injection of B16-BL-6 melanpmacells. (Ref. 3042)
High affinity antibodies against this ganglioside was obtained from a phage display library. (Ref. 3044)
This ganglioside was not the carbohydrate ligand of E-selectin. (Ref. 3051)
-17.5deg(Ref. 3005)
1D 1H-NMR (Ref. 3005)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-glucopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-D-glucopyranoside with methyl 2,3,4-tri-O-benzyl-1-thio-b-L-fucopyranoside gave the a-glycoside, which was converted by reductive ring-opening of the benzylidene acetal into the glycosyl acceptor. Dimethyl(methylthio)sulfonium triflate-promoted coupling of 6 with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside afforded the desired hexasaccharide in good yield.
This oligosaccharide was converted into the a-trichloroacetimidate, via reductive removal of the benzyl groups, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and treatment with trichloroacetonitrile, which, on coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycoside. Finally, the compound was transformed, via selective reduction of the azide group, condensation with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the title compound.(Ref. 3005)


Fatty acid C18:0

LCB d18:1
506
sialyl-(2-6)lactotetraosylceramide
N-acetylneraminyla2-6galactosylb1-3-N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3009
Hideharu Ishida
C73H131N3O32 1562.822 Download ChemDraw structure file
This ganglioside was restrictively bound by Influenza Virus B/Lee/40, but weakly by Influenza Virus A/PR/8, but.(Ref. 3032)
This ganglioside was less sensitive to the sialidase of influenza B virus isolates than the corresponding sialyl a2-6gal isomer. (Ref. 3036)
This ganglioside was recognized by the hemagglutinin of human influenza B virus isolates as well as the sorreponding 2-6 isomer. (Ref. 3038)
-5.2deg(Ref. 3006)
1D 1H-NMR (Ref. 3006)



Chemical Synthesis
Methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-6)-2,4-di-O-benzoyl-3-O-benzyl-1-thio-b-D-galactopyranoside, the key glycosyl donor was prepared, via glycosylation of 2-(trimethylsilyl)ethyl 3-O-benzyl-b-D-galactopyranoside with the methyl a-thio-glycoside of N-acetylneuraminic acid, benzoylation, replacement of the 2-(trimethylsilyl)ethyl group by acetyl, and introduction of the methylthio group with (methylthio)-trimethylsilane. Coupling of 2-(trimethylsilyl)ethyl O-(2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-glucopyranosyl)-(1-3')-per-O-benzyl-b-lactoside with the disaccharide donor gave the pentasaccharide in good yields. The oligosaccharide was converted into the corresponding a-trichloroacetimidate which, on coupling with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycoside.
Finally, the compound was transformed, via selective reduction of the azide group, condensation with octadecanoic acid, O-de-acylation, and hydrolysis of the methyl ester group, into the final compound. (Ref. 3006)


Fatty acid C18:0

LCB d18:1
507
sialyl-(2-6)-neolactotetraosylceramide/sialyl(2-6)-paragloboside
N-acetylneraminyla2-6galactosylb1-4-N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3010
Hideharu Ishida
C73H131N3O32 1562.822 Download ChemDraw structure file

-1.5deg(Ref. 3006)
1D 1H-NMR (Ref. 3006)



Chemical Synthesis
Methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-6)-2,4-di-O-benzoyl-3-O-benzyl-1-thio-b-D-galactopyranoside, the key glycosyl donor was prepared, via glycosylation of 2-(trimethylsilyl)ethyl 3-O-benzyl-b-D-galactopyranoside with the methyl a-thio-glycoside of N-acetylneuraminic acid, benzoylation, replacement of the 2-(trimethylsilyl)ethyl group by acetyl, and introduction of the methylthio group with (methylthio)-trimethylsilane. Coupling of 2-(trimethylsilyl)ethyl O-(2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1-3')-per-O-benzyl-b-lactoside with the disaccharide donor gave the pentasaccharide in good yields.
The oligosaccaride was converted into the corresponding a-trichloroacetimidate which, on coupling with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycoside. Finally, the compound was transformed, via selective reduction of the azide group, condensation with octadecanoic acid, O-de-acylation, and hydrolysis of the methyl ester group, into the final compound. (Ref. 3006)


Fatty acid C18:0

LCB d18:1
508
N-acetylneraminyla2-3galactosylb1-3-N-acetyl-galactosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3011
Hideharu Ishida
GM1b, cis GM1
C73H131N3O32 1562.822 Download ChemDraw structure file
This ganglioside is potent neuronal ligands for myelin-associated glycoprotein. (Ref. 3040)
+5.7deg(Ref. 3007)
1D 1H-NMR (Ref. 3007)



Chemical Synthesis
Coupling of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-a-D-galactopyranosyl bromide and 2-(trimethylsilyl)ethyl O-(2,3,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-trio-O-benzyl-b-D-galactopyranoside gave a trisaccharide, which after removal of O-acetyl-and phthaloylgroups was converted by benzylidenation into two a acceptor. This were suitable for C-3 glycosylation reaction, promoted by dimethyl(methylthio)sulfonium triflate (DMTST), with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside . The reations gave the pentasaccharide derivative in high yield, and this were transformed into the a-trichloroacetimidate.
Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the a-trichloroacetimidate gave the corresponding b-glycosides, which on channeling through selective reductionof the azido group, coupling of thus formed aminogroup with octadecanoic acid, O-deacetylation, and saponification of the methyl ester group, gave the target compound. (Ref. 3007)


Fatty acid C18:0

LCB d18:1
509
sialyl-(2-6)-Lex
N-acetylneraminyla2-6galactosylb1-3-N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3012
Hideharu Ishida
C79H141N3O36 1708.963 Download ChemDraw structure file
This ganglioside was recgnized by the three members of the selectin receptor family as a a common carbohydrate epitope. (Ref. 3033)
This ganglioside was not the carbohydrate ligand of E-selectin. (Ref. 3051>
-16.6deg(Ref. 3008)
1D 1H-NMR (Ref. 3008)



Chemical Synthesis
Dimethyl(methylthio)sulfonium triflate-promoted coupling of 2-(trimethylsilyl)ethyl O-(2,3,4-tri-O-benzyl-a-L-fucopyranosyl)-(1-3)-O-(2-acetamido-6-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-6)-2,4-di-O-benzoyl-3-O-benzyl-1-thio-b-D-galactopyranoside afforded the desired hexasaccharide. This was converted into the a-trichloroacetimidate, via reductive removal of the benzyl groups, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and treatment with trichloroacetonitrile, which, on coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycoside. Finally, the compound was transformed, via selective reduction of the azide group, condensation with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the title compound.(Ref. 3008)


Fatty acid C18:0

LCB d18:1
510
N-acetylneuraminyla2-3galactosylb1-3(N-acetylneuraminyla2-6)N-acetyl- -galactosaminylb1-4galactosylb1-4glucosylceramide
GSG3013
Hideharu Ishida
GD1a
C84H148N4O39 1838.077 Download ChemDraw structure file
This ganglioside is enriched in Purkinje cells and may have a role in Purkinje cell functions in the cerebellum. (Ref. 3041)
+3.4deg(Ref. 3009)
1D 1H-NMR (Ref. 3009)



Chemical Synthesis
Suitably protected pentasaccharide derivatives, derived from known pentasaccharide precursors, were selected as the glycosyl acceptors. Using our facile method of stereoselective a-glycosidation of sialic acid, these acceptors were coupled with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate in acetonitrile medium in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) to get the desired di-a-sialyl hexasaccharide derivative in moderate yield. The hexasaccharide trichloroacetimidate upon coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the corresponding b-linked sphingosine glycoside in high yield. This was subjected in sequence to selective reduction of the azido group and coupling of the thus formed amino group with octadecanoic acid, O-deacylation, and saponification of the methyl ester groups to obtain ganglioside GD1a . (Ref. 3009)


Fatty acid C18:0

LCB d18:1
511
N-acetyl-galactosaminylb1-4(N-acetylneraminyla2-3)galactosylb1-4glucosylceramide
GSG3014
Hideharu Ishida
GM2
C67H121N3O26 1384.682 Download ChemDraw structure file

+11.3deg(Ref. 3010)
1D 1H-NMR (Ref. 3010)



Chemical Synthesis
Coupling of 2- (trimethylsilyl)ethyl O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside, prepared from 2-(trimethylsilyl)ethyl b-lactoside by selective 3',4'-O-isopropylidenation, O-benzylation, and subsequent removal of the isopropylidene group, with methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate using N-iodosuccinimide (NIS), gave the trisaccharide), which on condensation with methyl 6-O-benzoyl -2-deoxy-3,4-O-isopropylidene-2-phthalimido-1-thio-b-D-galactopyranoside , gave the protected ganglioside GM2 oligosaccharide.
This was transformed, via O-deisopropylidenation, O-acetylation, removal of the phthaloyl group, N-acetylation, removal of the benzyl groups followed by O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the final glycosyl donor. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the a-trichloroacetimidate gave the b-glycoside, which on channeling through selective reduction of the azide group, coupling of the amino group with octadecanoic acid, O-deacylation and saponification of the methyl ester group, gave the title ganglioside. (Ref. 3010)


Fatty acid C18:0

LCB d18:1
512
N-acetylneraminyla2-8-N-acetylneraminyla2-3galactosylb1-4glucosylceramide
GSG3015
Hideharu Ishida
GD3
C70H125N3O29 1472.744 Download ChemDraw structure file

-2.6deg(Ref. 3011)
1D 1H-NMR (Ref. 3011)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl 2,3,6, 2',6'-penta-O-benzyl-b-lactoside, with methyl [phenyl 5-acetamido-4,7-di-O-acetyl-3,5-dideoxy-2-thio-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylono-1',9-lactone)-D-glycero-D-galacto-2-nonulopyranosid]onate, which was prepared from O-(5-acetamido-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonic acid)-(2-8)-5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid by treatment with Amberlite IR-120 (H+) in methanol, O-acetylation, and subsequent replacement of the anomeric acetoxy group with phenyl thio, using N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid (TfOH) as a promoter, gave the corresponding a-glycoside.
The tetrasaccharide was converted, via O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into a-trichloroacetimidate which, on coupling with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycoside. Finally,this was easily transformed, via selective reduction of the azido group, condensation with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester and lactone, into ganglioside GD3. (Ref. 3011)


Fatty acid C18:0

LCB d18:1
513
KDNa2-3galactosylb1-4glucosylceramide
GSG3016
Hideharu Ishida
KDN-GM3
C58H109NO21 1156.480 Download ChemDraw structure file
This ganglioside was cleaved by a novel sialidase isolated from the liver of loach, to release KDO. (Ref. 3039)
This ganglioside have the immunosuppressive properties of the natural molecules and are useful in probing which elements of ganglioside structure are critical to their biological activity.(Ref. 3002/3043)
-12.0deg(Ref. 3012)
1D 1H-NMR (Ref. 3012)



Chemical Synthesis
KDN, prepared by the condensation of oxalacetic acid with D-mannose, was converted via methylesterification, O-acetylation and replacement of the anomeric acetoxy group with phenylthio, into methyl (phenyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate . Glycosylation of the donor with 2-(trimethylsilyl)ethyl O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside was performed, using N-iodosuccinimide-trimethylsilyl trifluoromethanesulfonate as the glycosyl promoter, to give 2-(trimethylsilyl)ethyl O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-(6-O-benzoyl-b-D-galactopyrano-syl)-(1-4)-(2,6-di-O-benzoyl-b-D-glucopyranoside. The trysaccharide was converted via O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group and subsequent imidate formation, into the corresponding trichloroacetimidate.
Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with thedonor in the presence of boron trifluoride etherate afforded the expected b-glycoside, which wasa transformed via selective reduction of the azido group, coupling with octadecanoic acid, O-deacylation and de-esterification, into the target ganglioside. (Ref. 3012)


Fatty acid C18:0

LCB d18:1
514
KDNa2-3galactosylceramide
GSG3017
Hideharu Ishida
KDN-GM4
C55H103NO16 1034.403 Download ChemDraw structure file
This ganglioside have the immunosuppressive properties of the natural molecules and are useful in probing which elements of ganglioside structure are critical to their biological activity.(Ref. 3002)
-17.2deg(Ref. 3012)
1D 1H-NMR (Ref. 3012)



Chemical Synthesis
KDN, prepared by the condensation of oxalacetic acid with D-mannose, was converted via methylesterification, O-acetylation and replacement of the anomeric acetoxy group with phenylthio, into methyl (phenyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate . Glycosylation of 2 with 2-(trimethylsilyl)ethyl 6-O-benzoyl-b-D-galactopyranoside was performed, using N-iodosuccinimide-trimethylsilyl trifluoromethanesulfonate as the glycosyl promoter, to give 2-(trimethylsilyl)ethyl O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-6-O-benzoyl-b-D-galacto-pyranoside. The disaccharide was converted via O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group and subsequent imidate formation, into the corresponding trichloroacetimidate.
Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor in the presence of boron trifluoride etherate afforded the expected b-glycosides, which was transformed via selective reduction of the azido group, coupling with octadecanoic acid, O-deacylation and de-esterification, into the target ganglioside. (Ref. 3012)


Fatty acid C18:0

LCB d18:1
515
KDN-lactotetraosylceramide
KDNa2-3galactosylb1-3-N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3018
Hideharu Ishida
C75H136N2O32 1577.877 Download ChemDraw structure file

-6.8deg(Ref. 3013)
1D 1H-NMR (Ref. 3013)



Chemical Synthesis
4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside was prepared from 2-(trimethylsilyl)ethyl O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-6-O-benzyl-b-D-galactopyra-noside, via O-benzoylation, replacement of the 2-(trimethylsilyl)ethyl group by acetyl, and introduction of the methylthio group with methylthiotrimethylsilane.
Glycosylation of 2-(trimethylsilyl)ethyl O-(2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-glucopyra-nosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with the disaccharide donor gave the corresponding pentasaccharide in good yield. This oligosaccharide was converted via reductive removal of the benzyl groups and benzylidene group, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the corresponding trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor in the presence of boron trifluoride etherate afforded the expected b-glycoside, which was transformed via selective reduction of the azido group, coupling with octadecanoic acid, O-deacylation and de-esterification, into the target ganglioside in high yield. (Ref. 3013)


Fatty acid C18:0

LCB d18:1
516
KDN-neolactotetraosylceramide/KDN-paragloboside
KDNa2-3galactosylb1-4-N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3019
Hideharu Ishida
C75H136N2O32 1577.877 Download ChemDraw structure file

-10.6deg(Ref. 3013)
1D 1H-NMR (Ref. 3013)



Chemical Synthesis
Methyl O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside was prepared from 2-(trimethylsilyl)ethyl O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-6-O-benzyl-b-D-galactopyra-noside, via O-benzoylation, replacement of the 2-(trimethylsilyl)ethyl group by acetyl, and introduction of the methylthio group with methylthiotrimethylsilane. Glycosylation of 2-(trimethylsilyl)ethyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with the disaccharide donor gave the corresponding pentasaccharide in good yield.
This oligosaccharide was converted via reductive removal of the benzyl groups and benzylidene group, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the corresponding trichloroacetimidate Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor in the presence of boron trifluoride etherate afforded the expected b-glycoside, which was transformed via selective reduction of the azido group, coupling with octadecanoic acid, O-deacylation and de-esterification, into the target ganglioside in high yield. (Ref. 3013)


Fatty acid C18:0

LCB d18:1
517
KDN-Lex
KDNa2-3galactosylb1-4(fucosyla1-3)N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3020
Hideharu Ishida
C81H146N2O36 1724.018 Download ChemDraw structure file

-16.0deg(Ref. 3013)
1D 1H-NMR (Ref. 3013)



Chemical Synthesis
Methyl O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside was prepared from 2-(trimethylsilyl)ethyl O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-6-O-benzyl-b-D-galactopyra-noside, via O-benzoylation, replacement of the 2-(trimethylsilyl)ethyl group by acetyl, and introduction of the methylthio group with methylthiotrimethylsilane. Glycosylation of 2-(trimethylsilyl)ethyl O-(2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-glucopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside (5) or 2-(trimethylsilyl)ethyl
O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside, prepared from 5 via O-benzylation and reductive opening of the benzylidene acetal ring, with 4 gave the corresponding pentasaccharides 9 and 13 in good yields. In the same way, 4 was reacted with 2-(trimethylsilyl)ethyl O-(2,3,4-tri-O-benzyl-a-L-fucopyranosyl)-(1-3)-O-(2-acetamido-6-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopy-ranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranosidewith the disaccharide donor gave the hexasaccharide. This oligosaccharide was converted via reductive removal of the benzyl groups and benzylidene group, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the corresponding trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor in the presence of boron trifluoride etherate afforded the expected b-glycoside, which were transformed via selective reduction of the azido group, coupling with octadecanoic acid, O-deacylation and de-esterification, into the target ganglioside. (Ref. 3013)


Fatty acid C18:0

LCB d18:1
518
galactosylb1-3(N-acetylneuraminyla2-6)N-acetyl- -galactosaminylb1-4galactosylb1-4glucosylceramide
GSG3021
Hideharu Ishida
GM1a
C73H131N3O32 1562.822 Download ChemDraw structure file
This gangliosideis is not recognized by myelin-associated glycoprotein. (Ref. 3040)
Binding specificites of the sialoadhesin family of I-type lectins was examined by employing this ganglioside. (Ref. 3046)
+5.4deg(Ref. 3014)
1D 1H-NMR (Ref. 3014)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(2,3,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with the suitably protected galactosamine donor, methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-b-D-galactopyranoside gave the desired trisaccharide, which was transformed into the trisaccharide acceptor via removal of the phthaloyl and o-acetyl groups followed by N-acetylation. Glycosylation of this acceptor with methyl 3-O-benzyl-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside gave the asialo GM1 saccharide derivative, which was transformed into the acceptor by removal of benzylidene group.
Coupling of this gangliotetraose acceptor with phenyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate by use of NIS-TfOH afforded the desired GM1a oligosaccharide derivative in high yield, which was transformed, via removal of the benzyl group followed by O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group and subsequent imidate formation, into the final glycosyl donor. Condensation of this imidate derivative with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the b-glycoside, which on channeling through selective reduction of the azido group, coupling of the amino group with octadecanoic acid, O-deacylation and saponification of the methyl ester group, gave the title compound GM1a . (Ref. 3014)


Fatty acid C18:0

LCB d18:1
519
KDN-(2-6)lactotetraosylceramide
KDNa2-6galactosylb1-3-N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3022
Hideharu Ishida
C75H138N2O32 1579.893 Download ChemDraw structure file

-8.2deg(Ref. 3015)
1D 1H-NMR (Ref. 3015)



Chemical Synthesis
Methyl O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-6)-2,4-di-O-benzoyl-3-O-benzyl-1-thio-b-D-galactopyranoside was prepared from the phenyl b-thioglycoside derivative of KDN and 2-(trimethylsilyl)ethyl 3-O-benzyl-b-D-galactopyranoside in four steps. Coupling of 2-(trimethylsilyl)ethyl O-(2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-glucopyranosyl)-(1-3')-per-O-benzyl-b-lactoside with the donor gave the pentasaccharide in good yield. The pentasaccharide was converted into the corresponding a-trichloroacetimidate which, on glycosylation with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycoside. Finally, this was transformed, via selective reduction of the azido group, condensation with octadecanoic acid, O-deacylation, and saponification of the methyl ester group, into the target compound. (Ref. 3015)


Fatty acid C18:0

LCB d18:1
520
KDN-(2-6)-neolactotetraosylceramide/sialyl-(2-6)-paragloboside
KDNa2-6galactosylb1-4-N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3023
Hideharu Ishida
C75H136N2O32 1577.877 Download ChemDraw structure file

-6.1deg(Ref. 3015)
1D 1H-NMR (Ref. 3015)



Chemical Synthesis
Methyl O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-6)-2,4-di-O-benzoyl-3-O-benzyl-1-thio-b-D-galactopyranoside was prepared from the phenyl b-thioglycoside derivative of KDN and 2-(trimethylsilyl)ethyl 3-O-benzyl-b-D-galactopyranosidein four steps. Coupling of 2-(trimethylsilyl)ethyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1-3')-per-O-benzyl-b-D-lactoside, with the donor gave the pentasaccharidein good yields. This pentasaccharide was converted into the corresponding a-trichloroacetimidate which, on glycosylation with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycoside. Finally, this was transformed, via selective reduction of the azido group, condensation with octadecanoic acid, O-deacylation, and saponification of the methyl ester group, into the target compound. (Ref. 3015)


Fatty acid C18:0

LCB d18:1
521
3-sulfoglucuronylparagloboside
3-sulfoglucuronylb1-3galactosyl-b1-4-N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3024
Hideharu Ishida
SGPG
C68H119N2O32SNa2 1554.712 Download ChemDraw structure file


FAB-MS (negative ion mode); m/z 1531.91 (M-Na)-, 1553.89 (M-H)- (Ref. 3016)


Chemical Synthesis
Methyl (4-O-acetyl-2-O-benzoyl-3-O-levulinoyl-a-D-glucopyranosyl trichloroacetimidate)uronate) was prepared from methyl [2-(trimethylsilyl)ethyl b-D-glucopyranosid]uronate via selective 4-O-acetylation, 2-O-benzoylation, 3-O-levulinoylation, removal of the 2-(trimethylsilyl)ethyl group and imidate formation. The coupling of the donor with 2-(trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-b-D-galactopyranoside using trimethylsilyl trifluoromethanesulfonate gave 2-(trimethylsilyl)ethyl O-(methyl 4-O-acetyl-2-O-ben-zoyl-3-O-levulinoyl-b-D-glucopyranosyluronate)-(1-3)-2,4,6-tri-O-benzyl-b-D-galact-opyranoside, which was transformed via removal of the benzyl group, benzoylation, removal of the 2-(trimethylsilyl)ethyl group and imidate formation into the disaccharide donor. On the other hand, 2-(trimethylsilyl)ethyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside as the acceptor was prepared from
2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-b-D-glucopyranoside via O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, imidate formation, coupling with 2-(trimethylsilyl)ethyl O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyrano-side, removal of the O-acetyl and N-phthaloyl group followed by N-acetyla-tion. Condensation of thedisaccharide donor with the trisaccharide acceptor using trimethylsilyl trifluoromethanesulfonate afforded the desired pentasaccharide, which was transformed by removal of the benzyl group, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group and imidate formation into the pentasaccharide donor. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol withthe imidate gave the desired b-glycoside, which was transformed into the target compound, via reduction of the azido group, coupling with octadecanoic acid, selective removal of the levulinoyl group, O-sulfation, hydrolysis of the methyl ester group and O-deacylation. (Ref. 3016)


Fatty acid C18:0

LCB d18:1
522
3-sulfoglucuronylparagloboside
3-sulfoglucuronylb1-3galactosyl-b1-4-N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3025
Hideharu Ishida
SGPG
C74H131N2O32SNa2 1638.872 Download ChemDraw structure file


FAB-MS (negative ion mode); m/z 1615.85 (M-Na)-, 1637.66 (M-H)- (Ref. 3016)


Chemical Synthesis
Methyl (4-O-acetyl-2-O-benzoyl-3-O-levulinoyl-a-D-glucopyranosyl trichloroacetimidate)uronate) was prepared from methyl [2-(trimethylsilyl)ethyl b-D-glucopyranosid]uronate via selective 4-O-acetylation, 2-O-benzoylation, 3-O-levulinoylation, removal of the 2-(trimethylsilyl)ethyl group and imidate formation. The coupling of the donor with 2-(trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-b-D-galactopyranoside using trimethylsilyl trifluoromethanesulfonate gave 2-(trimethylsilyl)ethyl O-(methyl 4-O-acetyl-2-O-ben-zoyl-3-O-levulinoyl-b-D-glucopyranosyluronate)-(1-3)-2,4,6-tri-O-benzyl-b-D-galact-opyranoside, which was transformed via removal of the benzyl group, benzoylation, removal of the 2-(trimethylsilyl)ethyl group and imidate formation into the disaccharide donor. On the other hand, 2-(trimethylsilyl)ethyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside as the acceptor was prepared from 2-(trimethylsilyl)ethyl
3,6-di-O-benzyl-2-deoxy-2-phthalimido-b-D-glucopyranoside via O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, imidate formation, coupling with 2-(trimethylsilyl)ethyl O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyrano-side, removal of the O-acetyl and N-phthaloyl group followed by N-acetyla-tion. Condensation of thedisaccharide donor with the trisaccharide acceptor using trimethylsilyl trifluoromethanesulfonate afforded the desired pentasaccharide, which was transformed by removal of the benzyl group, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group and imidate formation into the pentasaccharide donor. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol withthe imidate gave the desired b-glycoside, which was transformed into the target compound, via reduction of the azido group, coupling with tetracosanoic acid, selective removal of the levulinoyl group, O-sulfation, hydrolysis of the methyl ester group and O-deacylation.(Ref. 3016)


Fatty acid C24:0

LCB d18:1
523
N-acetyl-galactosaminylb1-4(KDNa2-3)galactosylb1-4glucosylceramide
GSG3026
Hideharu Ishida
KDN-GM2
C65H118N2O27 1359.630 Download ChemDraw structure file

+8.2deg(Ref. 3017)
1D 1H-NMR (Ref. 3017)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(2,6-di-O-benzyl-b-D-galac-topyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with methyl 6-O-benzyl-2-deoxy-3,4-O-isopropylidene-2-phthalimido-1-thio-b-D-galactopyranoside gave the tetrasaccharide, which was converted, via de-esterification, removal of the phthaloyl group, N-acetylation, and O-deisopropylidenation, into the tetrasaccharide acceptor. Reductive removal of the benzyl groups in 9, O-acetylation and subse-quent removal of the 2-(trimethylsilyl)ethyl group followed by imidate formation, gave the KDN-GM2 oligosaccharide glycosyl donor. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor in the presence of boron trifluoride etherate afforded the expected b-glycoside, which was transformed in good yield, via selective reduction of the azido group, coupling with octadecanoic acid, O-deacylation, and de-esterification, into the target ganglioside.(Ref. 3017)


Fatty acid C18:0

LCB d18:1
524
galactosylb1-3N-acetyl-galactosaminylb1-4(KDNa2-3)galactosylb1-4glucosylceramide
GSG3027
Hideharu Ishida
KDN-GM1
C71H128N2O32 1521.770 Download ChemDraw structure file

+3.5deg(Ref. 3017)
1D 1H-NMR (Ref. 3017)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(2,6-di-O-benzyl-b-D-galac-topyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with methyl 6-O-benzyl-2-deoxy-3,4-O-isopropylidene-2-phthalimido-1-thio-b-D-galactopyranoside gave the tetrasaccharide, which was converted, via de-esterification, removal of the phthaloyl group, N-acetylation, and O-deisopropylidenation, into the tetrasaccharide acceptor. Glycosylation of the acceptor with methyl 2,4,6-tri-O-benzoyl-3-O-benzyl-1-thio-b-D-galacto-pyranoside, using dimethyl(methylthio)sulfonium triflate (DMTST), gave the pentasaccharide, which was converted via reductive removal of their benzyl groups, O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and reaction with trichloroacetonitrile, into the corresponding a-trichloroacetimidate.
Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor in the presence of boron trifluoride etherate afforded the expected b-glycoside, which was transformed in good yield, via selective reduction of the azido group, coupling with octadecanoic acid, O-deacylation, and de-esterification, into the target ganglioside.(Ref. 3017)


Fatty acid C18:0

LCB d18:1
525
KDNa2-3galactosylb1-3N-acetyl-galactosaminylb1-4(KDNa2-3)galactosylb1-4glucosylceramide
GSG3028
Hideharu Ishida
KDN-GD1a
C80H142N2O40 1771.973 Download ChemDraw structure file

-3.4deg(Ref. 3017)
1D 1H-NMR (Ref. 3017)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(2,6-di-O-benzyl-b-D-galac-topyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with methyl 6-O-benzyl-2-deoxy-3,4-O-isopropylidene-2-phthalimido-1-thio-b-D-galactopyranoside gave the tetrasaccharide, which was converted, via de-esterification, removal of the phthaloyl group, N-acetylation, and O-deisopropylidenation, into the tetrasaccharide acceptor. Glycosylation of the acceptor with methyl (methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside, using dimethyl(methylthio)sulfonium triflate (DMTST), gave the hexasaccharide, which was converted via reductive removal of their benzyl groups, O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and reaction with trichloroacetonitrile, into the corresponding a-trichloroacetimidate.
Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor in the presence of boron trifluoride etherate afforded the expected b-glycoside, which was transformed in good yield, via selective reduction of the azido group, coupling with octadecanoic acid, O-deacylation, and de-esterification, into the target ganglioside. (Ref. 3017)


Fatty acid C18:0

LCB d18:1
526
N-acetylneraminyla2-3galactosylb1-3-N-acetyl-galactosaminyl-b1-3galactosyl-a1-3galactosylb1-4glucosylceramide
GSG3029
Hideharu Ishida
C79H141N3O37 1724.963 Download ChemDraw structure file

-1.0deg(Ref. 3018)
1D 1H-NMR (Ref. 3018)



Chemical Synthesis
2-(Trimethylsilyl)ethyl 2-O-benzyl-4,6-O-benzylidene-a-D-galactopyranosyl-(1-3)-2,4,6-tri-O-benzyl-b-D-galactopyranosyl-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside, the core structure of isoglobo-series gangliosides was prepared by the glycosylation of 2-(trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-thio-b-D-galactopyranoside, and subsequent de-O-acetylation. Coupling of the trisaccharide acceptor and methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-b-D-galactopyranoside gave a isoglobotetraoside derivative, from which the phthaloyl and O-acetyl groups were removed.
N-Acetylation then gave a tetrasaccharide acceptor. Dimethyl(methylthio)sulfonium triflate-promoted coupling of the accptor with methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto)-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranosidegave the hexasaccharide derivativein good yield. Theoligosaccharide was converted into the corresponding a-trichloroimidate which, on coupling with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycoside. Finally, this was transformed, via selective reduction of the azide group, condensation with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the titleproduct. (Ref. 3018)


Fatty acid C18:0

LCB d18:1
527
3-sulfoglucuronyllactotsylparagloboside
3-sulfoglucuronylb1-3galactosylb1-4-N-acetyl-glucosaminylb1-3galactosylb1-4-N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3030
Hideharu Ishida
SGLPG
C82H143N3Na2O44S 1953.052 Download ChemDraw structure file


FAB-MS (negative ion mode); m/z 1896.82 (M-Na)-, 1918.69 (M-H)- (Ref. 3019)


Chemical Synthesis
Condensation of 2-(trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-b-D-galactopyranoside with 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-b-D-glucopyranosyl trichloroacetimidate gave the desired b-glycoside, which was converted into 2-(trimethylsilyl)ethyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-benzyl-b-D-galactopyranoside via removal of the O-acetyl and N-phthaloyl groups, followed by N-acetylation. Glycosylation ofthe disaccharide with O-(methyl 4-O-acetyl-2-O-benzoyl-3-O-levulinoyl-b-D-glucopyranosyluronate)-(1-3)-2,4,6-tri-O-benzoyl-a-D-galactopyranosyl trichloroacetimidate using trimethylsilyl trifluoromethanesulfonate gave the target tetrasaccharide, which was transformed via removal of the benzyl group, O-benzoylation, removal of the 2-(trimethylsilyl)ethyl group and imidate formation into the tetrasaccharide donor.
Glycosylation of 2-(trimethylsilyl)ethyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1- 3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1 - 4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with the imidate donor using trimethylsilyl trifluoromethanesulfonate gave the desired heptasaccharide which was transformed into the heptasaccharide imidate donor. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the heptasaccharide donor gave b-glycoside, which was transformed into the target compound, via reduction of the azido group, coupling with octadecanoic acid, selective removal of the levulinoyl group, O-sulfation, hydrolysis of the methyl ester group and O-deacylation. (Ref. 3019)


Fatty acid C18:0

LCB d18:1
528
3-sulfoglucuronyllactotsylparagloboside
3-sulfoglucuronylb1-3galactosylb1-4-N-acetyl-glucosaminylb1-3galactosylb1-4-N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3031
Hideharu Ishida
SGLPG
C88H155N3Na2O42S 2005.213 Download ChemDraw structure file


FAB-MS (negative ion mode); m/z 1980.92 (M-Na)-, 2003.85 (M-H)- (Ref. 3019)


Chemical Synthesis
Condensation of 2-(trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-b-D-galactopyranoside with 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-b-D-glucopyranosyl trichloroacetimidate gave the desired b-glycoside, which was converted into 2-(trimethylsilyl)ethyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-benzyl-b-D-galactopyranoside via removal of the O-acetyl and N-phthaloyl groups, followed by N-acetylation. Glycosylation ofthe disaccharide with O-(methyl 4-O-acetyl-2-O-benzoyl-3-O-levulinoyl-b-D-glucopyranosyluronate)-(1-3)-2,4,6-tri-O-benzoyl-a-D-galactopyranosyl trichloroacetimidate using trimethylsilyl trifluoromethanesulfonate gave the target tetrasaccharide, which was transformed via removal of the benzyl group, O-benzoylation, removal of the 2-(trimethylsilyl)ethyl group and imidate formation into the tetrasaccharide donor.
Glycosylation of 2-(trimethylsilyl)ethyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1- 3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1 - 4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with the imidate donor using trimethylsilyl trifluoromethanesulfonate gave the desired heptasaccharide which was transformed into the heptasaccharide imidate donor. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the heptasaccharide donor gave b-glycoside, which was transformed into the target compound, via reduction of the azido group, coupling with tetracosanoic acid, selective removal of the levulinoyl group, O-sulfation, hydrolysis of the methyl ester group and O-deacylation. (Ref. 3019)


Fatty acid C24:0

LCB d18:1
529
sialyl-dimeric Lex
N-acetylneuraminyla2-3galactosylb1-4(fucosyla1-3)N-acetyl-glucosaminylb1-3galactosylb1-4(fucosyla1-3)N-acetyl-glucosaminylb1-3galactosylb1-4glucosylceramide
GSG3032
Hideharu Ishida
C97H171N3O51 2195.385 Download ChemDraw structure file

-37.9deg(Ref. 3020)
1D 1H-NMR (Ref. 3032)



Chemical Synthesis
Regioselective glycosylation of the suitably protected Lewis X (Lex) pentasaccharide derivative with phenyl 4-O-acetyl-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-2-phthalimido-1-thio-b-D-glucopyranoside gave the hexasaccharide, which was converted, via removal of the phthaloyl groups and selective N-acetylation, into the hexasaccharide acceptor. Dimethyl(methylthio)sulfonium triflate (DMTST) promoted glycosylation of the acceptor with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2 - 3) - 2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside afforded regioselectively the expected octasaccharide, which was converted into the acceptor via O-acetylation and removal of the methoxybenzyl group.
Fucosylation of the acceotor with the methyl thioglycoside was performed by use of N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid(TfOH) as a promoter to give the desired nonasaccharide . After replacing the benzyl groups by the acetyl groups, the 2-(trimethylsilyl)ethyl group at the reducing end was selectively transformed into the a-trichloroacetimidate Coupling of the donor with (2S,3R,4E)-2-azido-3-O-tert-butyldiphenylsilyl-4-octadecene-1,3-diol gave the corresponding b-glycoside, which was transformed, via selective reduction of the azide group, coupling with octadecanoic acid, O-desilylation, O-deacylation, and hydrolysis of the methyl ester group, into the title ganglioside in good yield. (Ref. 3020)


Fatty acid C18:0

LCB d18:1
530
VIM-II
N-acetylneuraminyla2-3galactosylb1-4N-acetyl-glucosaminylb1-3galactosylb1-4(fucosyla1-3)N-acetyl-glucosaminylb1-3galactosylb1-4glucosylceramide
GSG3033
Hideharu Ishida
C91H161N3O47 2049.244 Download ChemDraw structure file

-17.4deg(Ref. 3021)
1D 1H-NMR (Ref. 3033)



Chemical Synthesis
Phenyl 2,3,4-tri-O-benzoyl-6-O-benzyl-b-D-galactopyranosyl-(1-4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-b-D-glucopyranoside, a key intermediate prepared by condensation of phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-b-D-glucopyranoside and 2,3,4-tri-O-benzoyl-6-O-benzyl-a-D-galactopyranosyl bromide, was glycosylated with methyl 2,3,4-tri-O-benzyl-1-thio-b-L-fucopyranoside to give the trisaccharide donor, which, on coupling with 2-(trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-b-D-galactopyranosyl-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside, afforded the pentasaccharide. The regioselective glycosylation of the acceptor, with phenyl 2,3,4-tri-O-benzoyl-6-O-benzyl-b-D-galactopyranosyl-(1-4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-b-D-glucopyranoside, gave the heptasaccharide, which was converted by treatment with hydrazine monohydrate and subsequent N-acetylation into the hexasaccharide acceptor.
The stereo- and regioselective glycosylation of the acceptor with methyl (phenyl 5-acetamido-4,7,8,9-O-benzoyl-3,5-dideoxy-2-thio-D-glycero-b-D-galacto-2-nonulopyranosid)onategave the desired octasaccharide. Hydrogenolytic removal of the benzyl groups and successive O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and treatment with trichloroacetonitrile gave the a-trichloroacetimidate which was then coupled with (2S,3R,4E)-2-azido-3-O-(tert-butyldiphenylsilyl)-4-octadecene-1,3-diol. The ompound was transformed, via selective reduction of the azido group, N-introduction of octadecanoic acid, O-desilylation, O-deacylation, and saponification of the methyl ester group, into the title VIM-2 ganglioside. (Ref. 3021)


Fatty acid C18:0

LCB d18:1
531
sialyl-Lea
N-acetylneraminyla2-3galactosylb1-3(fucosyla1-4)N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3034
Hideharu Ishida
C79H141N3O36 1708.963 Download ChemDraw structure file

-18.8deg(Ref. 3022)
1D 1H-NMR (Ref. 3022)



Chemical Synthesis
Methylsulfenyl bromide-silver triflate-promoted coupling of 2-(trimethylsilyl)ethyl O-(2-acetamido-6-O-benzy-2-deoxy-b-D-glucopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside afforded the pentasaccharide in good yield. Glycosylation of the pentasaccharide with methyl 2,3,4-tri-O-benzyl-1-thio-b-L-fucopyranoside by use of N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid (TfOH) as a promoter, gave the desired hexasaccharide.
This was converted into the a-trichloroacetimidate, via reductive removal of benzyl groups, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and treatment with trichloroacetonitrile, which, on coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycoside. Finally, the compound was transformed, via selective reduction of the azide group, coupling with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the title ganglioside in good yield. (Ref. 3022)


Fatty acid C18:0

LCB d18:1
532
N-acetylneuraminyla2-3galactosylb1-3(N-acetylneuraminyla2-6)N-acetyl- -galactosaminylb1-4(N-acetylneraminyla2-8N-acetylneraminyla2-3)galactosylb1-4glucosylceramide
GSG3035
Hideharu Ishida
GQ1ba
C106H182N6O55 2420.587 Download ChemDraw structure file
This ganglioside is the most potent neuronal ligands for myelin-associated glycoprotein. (Ref. 3040)
Binding specificites of the sialoadhesin family of I-type lectins was examined by employing this ganglioside. (Ref. 3046)
-13.0deg(Ref. 3023)
1D 1H-NMR (Ref. 3023)



Chemical Synthesis
Regio- and stereo-selective monosialylation of C-6 of N-acetylgalactosamine residue and the subsequent disialylation with methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate of C-3 of galactose residue with methyl [phenyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid]onateon 2-(trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-3,4-O-isopropylidene-b-D-galactopyranosyl)-(1-4)-O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-(1-4)-O-2,3,6-tri-O-benzyl-b-D-glucopyranoside by use of N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid (TfOH) as a promoter gave the corresponding hexasaccharide, containing a-glycosidicaly-linked monomeric sialic acid at
C-6 of N-acetylgalactosamine residue and dimeric sialic acid at C-3 of galactose residue on gangliotriose moiety, which was transformed into the acceptor by removal of isopropylidene group. Condensation of methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside with the hexasaccharide acceptor, using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter, gave the desired octasaccharide derivative in high yield. The introduction of the ceramide moiety into the octasaccharide, O-deacylation, and hydrolysis of the methyl ester group gave the title ganglioside in good yield. (Ref. 3023)


Fatty acid C18:0

LCB d18:1
533
N-acetylneraminyla2-8N-acetylneuraminyla2-3galactosylb1-3(N-acetylneraminyla2-8N-acetylneuraminyla2-6)N-acetyl- -galactosaminylb1-4galactosylb1-4glucosylceramide
GSG3036
Hideharu Ishida
GQ1b
C106H182N6O55 2420.587 Download ChemDraw structure file
This gangliosideis is not recognized by myelin-associated glycoprotein. (Ref. 3040)
+24.9deg(Ref. 3024)
1D 1H-NMR (Ref. 3024)



Chemical Synthesis
A fiRegio- and stereoselective dimeric sialylation of the hydroxyl group at C-6 of the GalNAc residue in 2-(trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-3-O-levulinyl-b-D-galactopyranosyl)-(1-4)-O-(2,3,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-O-2,3,6-tri-O-benzyl-b-D-glucopyranoside with methyl [phenyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galac-to-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-2-thio-D-glycero -D-galacto-2-nonulopyra-nosid]onate using N-iodosuccinimide (NIS)-trifluo-romethane-sulfonic acid (TfOH) as a promoter gave the desired pentasaccharide containing a-glycosidically-linked dimeric sialic acids. This was trans-formed into the acceptor by removal of the levulinyl group.
Condensation of methyl O-[methyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosylonate]-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside with the pentasaccharide acceptor, using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter, gave the desired octasaccharide derivative in high yield. The compound was converted into a-trichloroacetimidate, via reductive removal of the benzyl groups, O-acety-la-tion, removal of the 2-(trimethylsilyl)ethyl group, and treatment with trichloroace-toni-trile, which, on coupling with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycoside. Finally, the octasaccharide was transformed, via selective reduction of the azido group, coupling with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the title ganglioside in good yield.(Ref. 3024)



534
SSEA-4
N-acetylneraminyla2-3galactosylb1-3-N-acetyl-galactosaminyl-b1-3galactosyl-a1-4galactosylb1-4glucosylceramide
GSG3037
Hideharu Ishida
C79H141N3O37 1724.963 Download ChemDraw structure file

-3.0deg(Ref. 3025)
1D 1H-NMR (Ref. 3025)



Chemical Synthesis
a-Selective glycosylation of 2-(trimethylsilyl)ethyl O-(2,3,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with the suitably protected galactose donor, methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-thio-b-D-galactopyranoside gave the desired trisaccharide, which was transformed into the trisaccharide acceptor, by removal of the O-acetyl group. Glycosylation of this acceptor with methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-b-D-galactopyranoside gave the globotetraose derivative, which was transformed into the acceptor by removal of the phthaloyl and O-acetyl groups followed by N-acetylation.
DMTST promoted coupling of this acceptor with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-2,4,6-tri-O-ben-zoyl-1-thio-b-D-galactopyranoside afforded the desired sialyl globopentaoside derivative in good yield, which was transformed, by removal of the benzyl and benzylidene groups followed by O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group and subsequent imidate formation, into the final glycosyl donor. Condensation of this imidate derivative with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the b-glycoside, which on channeling through selective reduction of the azido group, coupling of the amino group with octadecanoic acid, O-deacylation and saponification of the methyl ester group, gave the title compound, sialyl globopentaosyl ceramide.(Ref. 3025)


Fatty acid C18:0

LCB d18:1
535
6-sulfo sialyl-Lex
N-acetylneraminyla2-3galactosylb1-4(fucosyla1-3)N-acetyl-6-sulfoglucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3038
Hideharu Ishida
C79H139N3Na2O39S 1832.991 Download ChemDraw structure file
This ganglioside, the putative L-selectin ligand, was detected on endothelial cells of high endothelial venules by a distinct set of anti-sialyl Lewis X antibodies. (Ref. 3045)
This ganglioside is the preferred ligand for L-selectin and de-N-acetylation of the sialic acid enhances the binding strength. (Ref. 3047)
IA major carbohydrate capping group of the L-selectin ligand on high endothelial venules in human lymph nodes was identified as 6-sulfo sialyl Lewis X. (Ref. 3048)
-5.7deg(Ref. 3026)
1D 1H-NMR (Ref. 3026)
FAB-MS (negative ion mode); m/z 1794 (M-Na)-, 1771 (M-2Na)-2 (Ref. 3026)


Chemical Synthesis
Coupling of the suitably protected N-acetyl-D-glucosaminyl-b(1-3)-lactose derivative with the sialyl a(2-3)-D-galactopyranosyl trichloroacetimidate, via glycosylation of 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-b-D-galactopyranoside with phenyl 2-thioglycoside derivative of N-acetylneuraminic acid (Neu5Ac) using N-iodosuccinimide/TfOH, O-benzoylation, removal of the benzylidene group, selective 6-O-levulinoylation, O-benzoylation, removal of the 2-(trimethylsilyl)ethyl group, and imidate formation, or via O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, then imidate formation, gave the pentasaccharide.
The glycosylation of the pentasaccharide acceptors, with phenyl 1-thioglycoside derivative of L-fucose using dimethyl(methylthio)sulfonium triflate (DMTST) afforded the corresponding hexasaccharides, which were transformed in good yields, via reductive removal of their benzyl groups, O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, imidate formation, coupling with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol in the presence of boron trifluoride etherate, selective reduction of the azido group, coupling with octadecanoic acid, selective removal of the levulinoyl groups, treatment with sulfur trioxide-pyridine complex, then removal of the protecting groups, into the desired sulfated sialyl Lex ganglioside analogues .(Ref. 3026)


Fatty acid C18:0

LCB d18:1
536
6'-sulfo sialyl-Lex
N-acetylneraminyla2-3(6-sulfo)galactosylb1-4(fucosyla1-3)N-acetylglucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3039
Hideharu Ishida
C79H139N3Na2O39S 1832.991 Download ChemDraw structure file
This ganglioside was not detected on endothelial cells of high endothelial venules by a distinct set of anti-sialyl Lewis X antibodies. (Ref. 3045)
-8.7deg(Ref. 3026)
1D 1H-NMR (Ref. 3026)
FAB-MS (negative ion mode); m/z 1794 (M-Na)-, 1771 (M-2Na)-2(Ref. 3026)


Chemical Synthesis
Coupling of the suitably protected N-acetyl-D-glucosaminyl-b(1-3)-lactose derivative with the sialyl a(2-3)-D-galactopyranosyl trichloroacetimidate, via glycosylation of 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-b-D-galactopyranoside with phenyl 2-thioglycoside derivative of N-acetylneuraminic acid (Neu5Ac) using N-iodosuccinimide/TfOH, O-benzoylation, removal of the benzylidene group, selective 6-O-levulinoylation, O-benzoylation, removal of the 2-(trimethylsilyl)ethyl group, and imidate formation, or via O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, then imidate formation, gave the pentasaccharide.
The glycosylation of the pentasaccharide acceptors, with phenyl 1-thioglycoside derivative of L-fucose using dimethyl(methylthio)sulfonium triflate (DMTST) afforded the corresponding hexasaccharides, which were transformed in good yields, via reductive removal of their benzyl groups, O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, imidate formation, coupling with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol in the presence of boron trifluoride etherate, selective reduction of the azido group, coupling with octadecanoic acid, selective removal of the levulinoyl groups, treatment with sulfur trioxide-pyridine complex, then removal of the protecting groups, into the desired sulfated sialyl Lex ganglioside analogues .(Ref. 3026)


Fatty acid C18:0

LCB d18:1
537
6,6'-bis-sulfo sialyl-Lex
N-acetylneraminyla2-3(6-sulfo)galactosylb1-4(fucosyla1-3)N-acetyl-6-sulfoglucosaminyl-b1-3galactosyl-b1-4glucosylceramide
GSG3040
Hideharu Ishida
C79H139N3Na2O39S 1832.991 Download ChemDraw structure file
This ganglioside, the putative L-selectin ligand, was detected on endothelial cells of high endothelial venules by a distinct set of anti-sialyl Lewis X antibodies. (Ref. 3045)
-10.3deg(Ref. 3026)
1D 1H-NMR (Ref. 3026)
FAB-MS (negative ion mode); m/z 1895 (M-Na)- (Ref. 3026)


Chemical Synthesis
Coupling of the suitably protected N-acetyl-D-glucosaminyl-b(1-3)-lactose derivative with the sialyl a(2-3)-D-galactopyranosyl trichloroacetimidate, via glycosylation of 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-b-D-galactopyranoside with phenyl 2-thioglycoside derivative of N-acetylneuraminic acid (Neu5Ac) using N-iodosuccinimide/TfOH, O-benzoylation, removal of the benzylidene group, selective 6-O-levulinoylation, O-benzoylation, removal of the 2-(trimethylsilyl)ethyl group, and imidate formation, or via O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, then imidate formation, gave the pentasaccharide.
The glycosylation of the pentasaccharide acceptors, with phenyl 1-thioglycoside derivative of L-fucose using dimethyl(methylthio)sulfonium triflate (DMTST) afforded the corresponding hexasaccharides, which were transformed in good yields, via reductive removal of their benzyl groups, O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, imidate formation, coupling with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol in the presence of boron trifluoride etherate, selective reduction of the azido group, coupling with octadecanoic acid, selective removal of the levulinoyl groups, treatment with sulfur trioxide-pyridine complex, then removal of the protecting groups, into the desired sulfated sialyl Lex ganglioside analogues .(Ref. 3026)


Fatty acid C18:0

LCB d18:1
538
N-acetyl-galactosaminylb1-6(N-acetylneraminyla2-3)galactosylb1-4glucosylceramide
GSG3041
Hideharu Ishida
6'-GM2
C67H121N3O26 1384.682 Download ChemDraw structure file
Structural basis for the resistance of Tay-sachs ganglioside GM2 to enzymatic degradation. was clarified by employing this ganglioside as a useful probe.(Ref. 3049)
+30.0deg(Ref. 3027)
1D 1H-NMR (Ref. 3027)



Chemical Synthesis
Removal of benzylidene group from 2-(trimethylsilyl)ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(4-methoxybenzyl)-b-D-galactopyranosyl-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside gave the lactose acceptor. The glycosylation of this compound with the oxazoline, which was prepared from the peracetylated derivative of GalNAc, in the presence of pyridinium p-toluenesulfonategave the desired b-glycoside in 61% yield. Removal of the 4-methoxybenzyl group afforded the expected glycosyl acceptor in 67% yield. Glycosylation of the acceptor with the phenyl 2-thioglycoside of Neu5Ac in the presence of N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid (TfOH) gave the expected a-glycoside. Removal of the benzyl groups and subsequent acetylation gave the peracetylated tetrasaccharide in 88% yield, which was converted into the corresponding trichloroacetimidate in good yield by selective removal of the 2-(trimethylsilyl)ethyl group and subsequent imidate formation.
The final glycosylation of (2S,3R,4E)-2-azido-3-O-(tert-butyldiphenylsilyl)-4-octadecene-1,3-diol with with the donor gave only the b-glycoside. Selective reduction of the azido group gave the amine , which on condensationwith octadecanoic acid furnished the fully protected target compound as follows: desilylation, and O-deacylation with sodium methoxide in methanol, and subsequent saponification of the methyl ester group, yielded the desired 6'-GM2 ganglioside. (Ref. 3027)


Fatty acid C18:0

LCB d18:1
539
N-acetylneraminyla2-8N-acetylneuraminyla2-3galactosylb1-3N-acetyl- -galactosaminylb1-4galactosylb1-4glucosylceramide
GSG3042
Hideharu Ishida
GD1c
C84H148N4O40 1854.077 Download ChemDraw structure file

+5.4deg(Ref. 3028)
1D 1H-NMR (Ref. 3028)



Chemical Synthesis
Condensation of methyl O-[methyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate]-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-gala-ctopyranoside with 2-(trimethylsilyl)ethyl O-(2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-galactopyranosyl)-(1-4)-O-(2,3,6-tri-O-benzyl-b-D-galactopy-ranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranosidegave the hexasaccharide derivative.
This oligosaccharides was converted into the a-trichloroacetimidate via reductive removal of the benzyl groups and/or benzylidene group, O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group and treatment with trichloroacetonitrile, which, on coupling with 2-azidosphingosine derivative gave the b-glycoside. Finally, this was transformed, via selective reduction of the azido group, coupling with octadecanoic acid and removal of all protecting groups, into the title gangliosides GD1c. (Ref. 3028)


Fatty acid C18:0

LCB d18:1
540
N-acetylneraminyla2-8N-acetylneuraminyla2-3galactosylb1-3N-acetyl- -galactosaminylb1-4(N-acetylneraminyla2-3)galactosylb1-4glucosylceramide
GSG3043
Hideharu Ishida
GT1a
C95H165N5O47 2129.332 Download ChemDraw structure file

+2.0deg(Ref. 3028)
1D 1H-NMR (Ref. 3028)



Chemical Synthesis
Condensation of methyl O-[methyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate]-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-gala-ctopyranoside with 2-(trimethylsilyl)ethyl O-(2-acetamido-6-O-benzyl-2-deoxy-b-D-galactopyranosyl)-(1-4)-O-[methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)]-O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyra-noside in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) gave the heptasaccharide derivative.
This oligosaccharides was converted into the a-trichloroacetimidate via reductive removal of the benzyl groups and/or benzylidene group, O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group and treatment with trichloroacetonitrile, which, on coupling with 2-azidosphingosine derivative gave the b-glycoside. Finally, this was transformed, via selective reduction of the azido group, coupling with octadecanoic acid and removal of all protecting groups, into the title ganglioside GT1a 19. (Ref. 3028)


Fatty acid C18:0

LCB d18:1
541
N-acetyl- galactosaminylb1-4(N-acetylneraminyla2-8N-acetylneraminyla2-3)galactosylb1-4glucosylceramide
GSG3044
Hideharu Ishida
GD2
C78H138N4O35 1691.936 Download ChemDraw structure file

-7.1deg(Ref. 3029)
1D 1H-NMR (Ref. 3029)



Chemical Synthesis
The glycosylation of the disialyl lactose acceptor with the suitably protected galactosamine donorin the presence of N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid gave the expected b-glycoside. Removal of the isopropylidene group gave andcatalytic hydrogenolysis of the benzyl group and subsequent O-acetylation, gave the peracetlated oligosaccharide. Treatment of the product with trifluoroacetic acid gave the 1-hydroxy compound. Treatment with trichloroacetonitrile gave the a-trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol23,24 with the donor afforded the desired b-glycoside .
Selective reduction of the azido group gave the amine which, on condensation with octadecanoic acid, using 1-ethyl-3-(3-dimethylaminopropyl)carbodi-imide hydrochloride (WSC) in dichloromethane, gave the acylated ganglioside. Finally O-deacylation with sodium methoxide in methanol, subsequent hydrolysis of the methyl ester and lactone, and treatment with ethylenediamine in n-butanol for 1 h at 70


Fatty acid C18:0

LCB d18:1
542
galactosylb1-3N-acetyl- galactosaminylb1-4(N-acetylneraminyla2-8N-acetylneraminyla2-3)galactosylb1-4glucosylceramide
GSG3045
Hideharu Ishida
GD1b
C84H148N4O40 1854.077 Download ChemDraw structure file

-1.2deg(Ref. 3030)
1D 1H-NMR (Ref. 3030)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(2-acetamido-6-O-benzyl-2-deoxy-3,4-O-iso-propylidene-b-D-galactopyranosyl)-(1-4)-O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with methyl [phenyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid]onate using N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid (TfOH) in acetonitrile gave the protected GD2 pentasaccharide, which was converted into the pentasaccharide acceptor by de-O-isopropylidenation. Glycosylation of the acceptor with methyl thioglycoside derivativeof galactose by use of dimethyl(methylthio)sulfonium triflate (DMTST) gave the protected GD1 oligosaccharide.
The compound was transformed into the corresponding a-trichloroacetimidate via reductive removal of benzyl groups, O-acetylation, selective removal of 2-(trimethylsilyl)ethyl group, and treatment of trichloroacetonitrile. Condensation of the imidate with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the corresponding b-glycoside, which was converted, via selective reduction of azido group, coupling with octadecanoic acid, de-O-acylation, and saponification of methyl esters and lactone groups, into the corresponding gangliosides GD1b.(Ref. 3030)


Fatty acid C18:0

LCB d18:1
543
galactosylb1-3N-acetyl- galactosaminylb1-4(N-acetylneraminyla2-8N-acetylneraminyla2-3)galactosylb1-4glucosylceramide
GSG3046
Hideharu Ishida
GD1b
C95H165N5O48 2145.331 Download ChemDraw structure file

-12.9deg(Ref. 3030)
1D 1H-NMR (Ref. 3030)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(2-acetamido-6-O-benzyl-2-deoxy-3,4-O-iso-propylidene-b-D-galactopyranosyl)-(1-4)-O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with methyl [phenyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyra-nosid]onate using N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid (TfOH) in acetonitrile gave the protected GD2 pentasaccharide, which was converted into the pentasaccharide acceptor by de-O-isopropylidenation.
Glycosylation of the acceptor with methyl thioglycoside derivative of sialyl galactose by use of dimethyl(methylthio)sulfonium triflate (DMTST) gave the protected ganglioside GT1b oligosaccharide. This was transformed into the corresponding a-trichloroacetimidate via reductive removal of benzyl groups, O-acetylation, selective removal of 2-(trimethylsilyl)ethyl group, and treatment of trichloroacetonitrile. Condensation of the imidate with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the corresponding b-glycoside, which was converted, via selective reduction of azido group, coupling with octadecanoic acid, de-O-acylation, and saponification of methyl esters and lactone groups, into the corresponding ganglioside GT1b.(Ref. 3030)


Fatty acid C18:0

LCB d18:1
544
galactosylb1-3N-acetyl- galactosaminylb1-4(N-acetylneraminyla2-8N-acetylneraminyla2-3)galactosylb1-4glucosylceramide
GSG3047
Hideharu Ishida
GD1b
C106H182N6O56 2436.586 Download ChemDraw structure file

-22.0deg(Ref. 3030)
1D 1H-NMR (Ref. 3030)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(2-acetamido-6-O-benzyl-2-deoxy-3,4-O-iso-propylidene-b-D-galactopyranosyl)-(1-4)-O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with methyl [phenyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyra-nosid]onate using N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid (TfOH) in acetonitrile gave the protected GD2 pentasaccharide, which was converted into the pentasaccharide acceptor by de-O-isopropylidenation.
Glycosylation of the acceptor with methyl thioglycoside derivative of disialyl galactose by use of dimethyl(methylthio)sulfonium triflate (DMTST) gave the protected ganglioside GQ1b oligosaccharide. This was transformed into the corresponding a-trichloroacetimidate via reductive removal of benzyl groups, O-acetylation, selective removal of 2-(trimethylsilyl)ethyl group, and treatment of trichloroacetonitrile. Condensation of the imidate with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the corresponding b-glycoside, which was converted, via selective reduction of azido group, coupling with octadecanoic acid, de-O-acylation, and saponification of methyl esters and lactone groups, into the corresponding ganglioside GQ1b.(Ref. 3030)


Fatty acid C18:0

LCB d18:1
545
N-acetylneuraminyla2-3galactosylb1-3(N-acetylneuraminyla2-6)N-acetyl- -galactosaminylb1-4(N-acetylneraminyla2-3)galactosylb1-4glucosylceramide
GSG3048
Hideharu Ishida
GT1aa
C95H165N5O48 2145.331 Download ChemDraw structure file

+2.0deg
1D 1H-NMR (Ref. 3031)
FAB MS (negative ion mode, triethanolamine matrix): 2172.04 [M-Na]-, 2150.06, 2149.07 [M-2Na]-, 2127.06 [M - 3Na]-,


Chemical Synthesis
The suitably protected sialyl-a-(2-6)-gangliotriose (III6NeuAc-GgOse) derivative was glycosylated with the phenyl 2-thioglycoside of sialic acid in the presence of N-iodosuccinimide (NIS) and trimethylsilyl trifluoromethanesulfonate (TMSOTf) in acetonitrile medium, giving the disialogangliotriose (III6NeuAcII3NeuAc-GgOse) derivative which contains both sialyl-a(2-6)-GalNAc and sialyl-a(2-3)-Gal structures. This pentasaccharide was efficiently synthesized by the coupling of (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-6)-2-deoxy-4,6-O-isopropylidene-2-phthalimido-D-galactopyranosyl trichloroacetimidate with 2-(trimethylsilyl)ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-(2,6-di-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside,
followed by conversion of the phthalimido group to the acetamido group. O-Deisopropylidenation and further glycosylation with methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside, promoted by dimethyl(methylthio)sulfonium triflate (DMTST), gave the desired trisialogangliotetraose (IV3NeuAcIII6NeuAcII3NeuAc-GgOse4) derivative, which was converted stepwise into the title ganglioside GT1aa- by the introduction of the ceramide part and then complete deprotection. (Ref. 3031)



LCB d18:1
546
N-acetylneraminyla2-8N-acetylneraminyla2-8N-acetylneraminyla2-3galactosylb1-4glucosylceramide
GSG3049
Hideharu Ishida
GT3
C81H142N4O37 1763.999 Download ChemDraw structure file

-11.6deg(Ref. 3052)
1D 1H-NMR (Ref. 3052)



Chemical Synthesis
Methyl [phenyl 5-acetamido-8-O-[5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylono-1",9'-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylono-1',9-lactone]-4,7-di-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid]onate was prepared from free, trimeric sialic acid, via lactonization, methyl esterification of the carboxyl group at the reducting end, O-acetylation and conversion of the anomeric acetoxy group into a phenylthio group. Iodonium promoted glycosylation of the donor with the lactose acceptor gave the pentasaccharidesaving the (Neu5Ac)3-Lac structure.
The peracylated oligosaccharide was converted into the a-trichloroacetimidate and coupled with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol to afford the corresponding b-glycoside. This protected azidosphingosine derivative was transformed into the target ganglioside GT3 via selective reduction of the azido group, subsequent coupling with octadecanoic acid, O-deacylation and saponification of the methyl ester and lactone groups. (Ref. 3052)



547
N-acetylneraminyla2-8N-acetylneraminyla2-8N-acetylneraminyla2-3galactosylceramide
GSG3050
Hideharu Ishida
GT4
C75H132N4O32 1601.858 Download ChemDraw structure file

-11.6deg(Ref. 3052)
1D 1H-NMR (Ref. 3052)



Chemical Synthesis
Methyl [phenyl 5-acetamido-8-O-[5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylono-1",9'-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylono-1',9-lactone]-4,7-di-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid]onate was prepared from free, trimeric sialic acid, via lactonization, methyl esterification of the carboxyl group at the reducting end, O-acetylation and conversion of the anomeric acetoxy group into a phenylthio group. Iodonium promoted glycosylation of the donor with 2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-b-D-galacto-pyranoside gave the corresponding tetrasaccharide having the (Neu5Ac)3-Gal structure.
The peracylated oligosaccharide was converted into the a-trichloroacetimidate and coupled with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol to afford the corresponding b-glycoside. This protected azidosphingosine derivative was transformed into the target ganglioside GT3 via selective reduction of the azido group, subsequent coupling with octadecanoic acid, O-deacylation and saponification of the methyl ester and lactone groups. (Ref. 3052)



548
sulfatide
3-sulfo-GalCer
GSG3051
Hideharu Ishida
C42H82NNaO11S 832.156 Download ChemDraw structure file
Sulfatide does not support MAG-mediated adhesion.(Ref. 3040)
Sulfatide is a ligand for a lymphocyte homing receptor, L-selectin (LECAM-1), binding epitope in sulfated sugar chain.(Ref. 3066)
Sulfatide has significant in vivo protective effects in neutrophil and selectin-dependent models of lung injury.(Ref. 3067)
Sulfatide showed inhbitory activity on B cell proliferation and Ig production as a ligand for L-selectin.(Ref. 3068)
Sulfatide showed in vitro and in vivo selectin-blocking activities(Ref. 3069)
217-219deg(decomp)(Ref. 3053)
1D 1H-NMR (Ref. 3053)

ion-spray MS (negative ion mode): m/z 806.5 [M-Na]-, (positive ion mode): m/z 808.5 [M-Na+2H]-

Chemical Synthesis
The 3-O-levulinoyl derivative of galactopyranosyl trichloroacetimidate was coupled with (2S,3R,4E)-3-O-acetyl-2-octadecanamido-4-octadecene-1,3-diol. The resulting glycolipid was transformed, by selective removal of the levulinoyl group, and successive sulfation and de-O-acylation, into the sulfatide.(Ref. 3053)


Fatty acid 18:0

LCB d18:1
549
GM4 position isomer
NeuAc2-6GalCer
GSG3052
Hideharu Ishida
C49H90N2O16 963.243 Download ChemDraw structure file

+1.0deg(Ref. 3003)
1D 1H-NMR (Ref. 3003)



Chemical Synthesis
The glycosylation of 2-(trimethylsilyl)ethyl 3-O-benzoyl-b-D-galactopyranoside with the sialyl donor using dimethyl(methylthio)sulfonium triflate (DMTST) gave the corresponding a-glycosides of Neu5Ac. Coupling of the trichloroacetimidate with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the corresponding b-glycoside, which was converted via selective reduction of the azide group, condensation with tetradecanoic acid, O-deacylation, and hydrolysis of the methyl ester group into the title compound. (Ref. 3003)


Fatty acid 18:0

LCB d18:1
550
GM4 analog
NeuAc2-6GlcNAcCer
GSG3053
Hideharu Ishida
C55H101N3O16 1060.401 Download ChemDraw structure file

-38.8deg(Ref. 3054)
1D 1H-NMR (Ref. 3054)



Chemical Synthesis
2-(Trimethylsilyl)ethyl sialyl-a(2-6)-2-acetamido-2-deoxy-b-D-glucopyranoside was converted into the corresponding oxazoline which, on coupling with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the corresponding b-glycoside. Finally, the b-glycoside was transformed, via selective reduction of the azide group, condensation with octadecanoic acid, O-deacylation and hydrolysis of the methyl ester group, into the title compound.(Ref. 3054)


Fatty acid 18:0

LCB d18:1
551
GM4 analog
NeuAc2-6GlcCer
GSG3054
Hideharu Ishida
C55H101N3O16 1060.401 Download ChemDraw structure file

-11.1deg(Ref. 3054)
1D 1H-NMR (Ref. 3054)



Chemical Synthesis
2-(Trimethylsilyl)ethyl sialyl-a(2-6)-b-D-glucopyranoside derivative was converted into the corresponding a-trichloroacetimidate which, on coupling with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the corresponding b-glycoside. Finally, the b-glycoside was transformed, via selective reduction of the azide group, condensation with octadecanoic acid, O-deacylation and hydrolysis of the methyl ester group, into the title compound.(Ref. 3054)


Fatty acid 18:0

LCB d18:1
552
GM3 positional isomer
NeuAc2-6Galb1-4GlcCer
GSG3055
Hideharu Ishida
C59H108N2O21 1181.490 Download ChemDraw structure file
This ganglioside is not a substrate of the trypanosoma crusi trans-sialidase.(Ref. 3070)
+8.9deg(Ref. 3055)
1D 1H-NMR (Ref. 3055)



Chemical Synthesis
Reductive removal of the benzyl groups in 2-(trimethylsilyl)ethyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-6)-(2-O-acetyl-3-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-b-D-glucopyranoside, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group , and treatment with trichloroacetonitrile, which, on coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycoside. Finally, the compound was transformed, via selective reduction of the azide group, condensation with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the title compound.(Ref. 3055)


Fatty acid 18:0

LCB d18:1
553
GM1b positional isomer
NeuAc2-6Galb1-3GalNAcb1-4Galb1-4GlcCer
GSG3056
Hideharu Ishida
C73H131N3O32 1562.822 Download ChemDraw structure file

-4.2deg(Ref. 3007)
1D 1H-NMR (Ref. 3007)



Chemical Synthesis
Sialyl a2-6Gal donor was coupled with 3'''-OH of the suitably protected GalNAcb1-4Lac to give the pentasaccharide, which was transformed into the a-trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the a-trichloroacetimidate gave the corresponding b-glycosides, which on channeling through selective reductionof the azido group, coupling of thus formed aminogroup with octadecanoic acid, O-deacetylation, and saponification of the methyl ester group, gave the target compound. (Ref. 3007)


Fatty acid 18:0

LCB d18:1
554
GM1b positional isomer
NeuAc2-3Galb1-6GalNAcb1-4Galb1-4GlcCer
GSG3057
Hideharu Ishida
C73H131N3O32 1562.822 Download ChemDraw structure file

+12.0deg(Ref. 3007)
1D 1H-NMR (Ref. 3007)



Chemical Synthesis
Sialyl a2-3Gal donor was coupled with 6'''-OH of the suitably protected GalNAcb1-4Lac to give the pentasaccharide, which was transformed into the a-trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the a-trichloroacetimidate gave the corresponding b-glycosides, which on channeling through selective reductionof the azido group, coupling of thus formed aminogroup with octadecanoic acid, O-deacetylation, and saponification of the methyl ester group, gave the target compound. (Ref. 3007)


Fatty acid 18:0

LCB d18:1
555
GM1b positional isomer
NeuAc2-6Galb1-6GalNAcb1-4Galb1-4GlcCer
GSG3058
Hideharu Ishida
C73H131N3O32 1562.822 Download ChemDraw structure file

+11.5deg(Ref. 3007)
1D 1H-NMR (Ref. 3007)



Chemical Synthesis
Sialyl a2-6Gal donor was coupled with 6'''-OH of the suitably protected GalNAcb1-4Lac to give the pentasaccharide, which was transformed into the a-trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the a-trichloroacetimidate gave the corresponding b-glycosides, which on channeling through selective reductionof the azido group, coupling of thus formed aminogroup with octadecanoic acid, O-deacetylation, and saponification of the methyl ester group, gave the target compound. (Ref. 3007)


Fatty acid 18:0

LCB d18:1
556
GD3 positional isomer
NeuAc2-9NeuAc2-3Galb1-4GlcCer
GSG3059
Hideharu Ishida
C70H125N3O29 1472.744 Download ChemDraw structure file
This ganglioside is not a substrate of the trypanosoma crusi trans-sialidase..(Ref. 3070)
+8.2deg(Ref. 3056)
1D 1H-NMR (Ref. 3056)



Chemical Synthesis
Coupling of 2-(trimethylsilyl)ethyl O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-9)-(methyl 5-acetamido-4,7,8-tri-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate using N-iodosuccinimide-trifluoromethanesulfonic acid as a glycosyl promoter, gave the tetrasaccharide, which was converted, via O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the O-(a-Neu5Ac)-(2-9)-O-(a-Neu5Ac)-(2-3')-a-lactosyl trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor afforded the b-glycoside, which was transformed, via selective reduction of the azide group, coupling with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the title ganglioside.(Ref. 3056)


Fatty acid 18:0

LCB d18:1
557
sialyl-Lex (pentasaccharide homolog)
NeuAc2-3Galb1-4(Fuca1-3)GlcNAcb1-3GalCer
GSG3060
Hideharu Ishida
C73H131N3O31 1546.823 Download ChemDraw structure file
This ganglioside, sLex penta glycolipid was recognized by pl-ELAM COS cells, but not as avidly as sLex hexa glycolipid.(Ref. 3051)
All three selectins bound to adsorbed sLex-penta-cer.(Ref. 3071)
-18.5deg(Ref. 3057)
1D 1H-NMR (Ref. 3057)



Chemical Synthesis
Königs-Knorr condensation of 2-(trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-b-D-galactopyranoside with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide gave the desired b-linked disaccharide, which was further coupled with methyl 2,3,4-tri-O-benzyl-1-thio-b-L-fucopyranoside to give the fucosylated derivative, which was transformed by reductive ring-opening of the benzylidene acetal into the trisaccharide acceptor. Dimethyl(methylthio)sulfonium triflate (DMTST)-promoted coupling of the acceptor with the NeuAc2-3Gal donor afforded the desired pentasaccharide, which was converted into the a-trichloroacetimidate and condensed with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol to give the b-glycoside, which was transformed into the title compound, via reduction of the azido group, coupling with octadecanoic acid, O-deacylation and hydrolysis of the methyl ester group.(Ref. 3057)


Fatty acid 18:0

LCB d18:1
558
GD1a positional isomer
NeuAc2-6Galb1-3(NeuAc2-6)GalNAcb1-4Galb1-4GlcCer
GSG3061
Hideharu Ishida
C84H148N4O39 1838.077 Download ChemDraw structure file

+1.2deg(Ref. 3009)
1D 1H-NMR (Ref. 3009)



Chemical Synthesis
Suitably protected sialyl2-6gangliotetraose derivative was coupled with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate in acetonitrile medium in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) to get the desired di-a-sialyl hexasaccharide derivative in moderate yield. The hexasaccharide trichloroacetimidate upon coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the corresponding b-linked sphingosine glycoside in high yield. This was subjected in sequence to selective reduction of the azido group and coupling of the thus formed amino group with octadecanoic acid, O-deacylation, and saponification of the methyl ester groups to obtain a positional isomer of ganglioside GD1a . (Ref. 3009)


Fatty acid 18:0

LCB d18:1
559
sialyl-Lex positional isomer
NeuAc2-3Galb1-4(Fuca1-3)GlcNAcb1-6Galb1-4GlcCer
GSG3062
Hideharu Ishida
C79H141N3O36 1708.963 Download ChemDraw structure file

-28.3deg(Ref. 3058)
1D 1H-NMR (Ref. 3058)



Chemical Synthesis
Tetrasaccharide containing GlcNAcb1-6Gal residue was obtained by glycosylation of 2-(trimethylsilyl)ethyl O-(2,3-di-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with methyl O-(2,3,4-tri-O-benzyl-a-L-fucopyranosyl)-(1-3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-b-D-glucopyranoside. The tretrasaccharide obtained was transformed into the acceptor. Dimethyl (methylthio)sulfonium triflate (DMTST)-promoted coupling of the accrptor with the NeuAc2-3Gal donor gave the desired hexasaccharide, which was converted , into the desired positional isomer of sialylLex gangliosides by our established procedures.(Ref. 3058)


Fatty acid 18:0

LCB d18:1
560
sialyl-Lex (tetrasaccharide homolog)
NeuAc2-3Galb1-4(Fuca1-3)GlcCer
GSG3063
Hideharu Ishida
C65H118N2O25 1327.631 Download ChemDraw structure file

-21.5deg(Ref. 3059)
1D 1H-NMR (Ref. 3059)



Chemical Synthesis
Condensation of O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(4-O-acetyl-2,6-di-O-benzoyl-b-D-galactopyranosyl)-(1-4)-O-[(2,3,4-tri-O-acetyl-a-L-fucopyranosyl)-(1-3)]-2,4-di-O-benzoyl-a-D-glucopyranosyl trichloroacetimidate with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the corresponding b-glycoside, which was converted into the gangliosid via selective reduction of the azido group, coupling with octadecanoic acid, O-deacylation, and saponification of the methyl ester group.(Ref. 3059)


Fatty acid 18:0

LCB d18:1
561
sialyl-Lex (pentasaccharide homolog)
NeuGc2-3Galb1-4(Fuca1-3)GlcNAcb1-3GalCer
GSG3064
Hideharu Ishida
C73H131N3O31 1546.823 Download ChemDraw structure file

-16.8deg(Ref. 3060)
1D 1H-NMR (Ref. 3060)



Chemical Synthesis
Königs-Knorr condensation of 2-(trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-b-D-galactopyranoside with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide gave the desired b-linked disaccharide, which was further coupled with methyl 2,3,4-tri-O-benzyl-1-thio-b-L-fucopyranoside to give the fucosylated derivative, which was transformed by reductive ring-opening of the benzylidene acetal into the trisaccharide acceptor. Dimethyl(methylthio)sulfonium triflate (DMTST)-promoted coupling of the acceptor with the NeuGc2-3Gal donor afforded the desired pentasaccharide, which was converted into the a-trichloroacetimidate and condensed with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol to give the b-glycoside, which was transformed into the title compound, via reduction of the azido group, coupling with octadecanoic acid, O-deacylation and hydrolysis of the methyl ester group.(Ref. 3060)


Fatty acid 18:0

LCB d18:1
562
SSEA-4 positional isomer
NeuAc2-6Galb1-3GalNAcb1-3Gala1-4Galb1-4GlcCer
GSG3065
Hideharu Ishida
C79H141N3O37 1724.963 Download ChemDraw structure file

-2.0deg(Ref. 3025)
1D 1H-NMR (Ref. 3025)



Chemical Synthesis
a-Selective glycosylation of 2-(trimethylsilyl)ethyl O-(2,3,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with the suitably protected galactose donor, methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-thio-b-D-galactopyranoside gave the desired trisaccharide, which was transformed into the trisaccharide acceptor, by removal of the O-acetyl group. Glycosylation of this acceptor with methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-b-D-galactopyranoside gave the globotetraose derivative, which was transformed into the acceptor by removal of the phthaloyl and O-acetyl groups followed by N-acetylation. DMTST promoted coupling of this acceptor with NeuAc-(2-6)-Gal donor afforded the positional isomer of sialyl globopentaoside derivative in good yield, which was transformed, by removal of the benzyl and benzylidene groups followed by O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group and subsequent imidate formation, into the final glycosyl donor.
Condensation of this imidate derivative with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the b-glycoside, which on channeling through selective reduction of the azido group, coupling of the amino group with octadecanoic acid, O-deacylation and saponification of the methyl ester group, gave the title compound, sialyl globopentaosyl ceramide.(Ref. 3025)


Fatty acid 18:0

LCB d18:1
563
6-sulfo-de-N-acetyl sialyl-Lex
Neu2-3Galb1-4(Fuca1-3)(6-sulfo)GlcNAcb1-3Galb1-4GlcCer
GSG3066
Hideharu Ishida
C77H137N3Na2O37S 1774.955 Download ChemDraw structure file
This ganglioside is a superio ligand for human L-selectin.(Ref. 3061)


FAB-MS (negative ion mode, triethanolamine matrix): m/z 1795.6 (M-H+Na)-, 1773.0 (M-H)-, 1750.6 (M-Na)- (Ref. 3061)

Chemical Synthesis
Glycosylation of NeuTFAc donor, which was readily prepared from phenyl 2-thioglycoside of NeuAc, and the Gal acceptor was performed to give the desired sialyla(2-3)Gal derivative, which was converted into the trichloroacetimidate derivative. Coupling of the donor with the suitably protected trisaccharide acceptor gave the sialyla(2-3)neolactotetraose derivative. The 3-OH of the GlcNAc residue was then fucosylated . The resulting sialyl Lex hexasaccharide derivative was converted to the trichloroacetimidate . Glycosylation of the azidosphingosine derivative with the donor, and successive reduction of the azido group and N-acylation were carried out by the established method. The levulinoyl group was selectively removed by treatment with hydrazine monoacetate without cleavage of the TFAc group. The deprotected 6-OH of the GlcNAc residue was then sulfated by treatment with sulfur trioxide-pyridine complex. Finally, removal of all protective groups under the basic conditions furnished the target molecule .(Ref. 3061)


Fatty acid 18:0

LCB d18:1
564
GT4 positional isomer
NeuAc2-8NeuAc2-8NeuAc2-6GalCer
GSG3067
Hideharu Ishida
C75H132N4O32 1601.858 Download ChemDraw structure file

-11.6deg(Ref. 3052)
1D 1H-NMR (Ref. 3052)



Chemical Synthesis
Trineric NeuAc donor was prepared from free, trimeric sialic acid, via lactonization, methyl esterification of the carboxyl group at the reducting end, O-acetylation and conversion of the anomeric acetoxy group into a phenylthio group. Iodonium promoted glycosylation of the donor with 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-b-D-galactopyranoside gave the corresponding tetrasaccharide having the a2-6 linked (Neu5Ac)3-Gal structure. The peracylated oligosaccharide was converted into the a-trichloroacetimidate and coupled with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol to afford the corresponding b-glycoside. This protected azidosphingosine derivative was transformed into the GT4 positional isomer via selective reduction of the azido group, subsequent coupling with octadecanoic acid, O-deacylation and saponification of the methyl ester and lactone groups. (Ref. 3052)


Fatty acid 18:0

LCB d18:1
565
GM3 analog
8-epi-NeuAc2-3Galb1-4GlcCer
GSG3068
Hideharu Ishida
C59H108N2O21 1181.490 Download ChemDraw structure file
8-Epi-GM3 was almost devoid of immunosupressive activity compared with native GM3.(Ref. 3002)
C-8-Epimerizationn in the neuraminic acid of GM3 impair the ability of trypanosoma crusi trans-sialidase to donate the modified sialic acid. (Ref. 3070)
-0.7deg(Ref. 3062)
1D 1H-NMR (Ref. 3062)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside with the methylthio glycoside of 8-epi-NeuAc gave the corresponding 2-(trimethylsilyl)ethyl sialyl a(2-3')-b-lactoside, which were converted, via O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the sialyl a(2-3')-lactose trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor afforded the corresponding b-glycoside, which was transformed, via selective reduction of the azide group, coupling with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the end product.(Ref. 3062)


Fatty acid 18:0

LCB d18:1
566
GM3 analog
4-methoxy-NeuAc2-3Galb1-4GlcCer
GSG3069
Hideharu Ishida
C60H110N2O21 1195.516 Download ChemDraw structure file
C-4-Methylation in the neuraminic acid of GM3 impair the ability of trypanosoma crusi trans-sialidase to donate the modified sialic acid. (Ref. 3070)
+3.0deg(Ref. 3062)
1D 1H-NMR (Ref. 3062)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside with the methylthio glycoside of 4-methoxy-NeuAc gave the corresponding 2-(trimethylsilyl)ethyl sialyl a(2-3')-b-lactoside, which were converted, via O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the sialyl a(2-3')-lactose trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor afforded the corresponding b-glycoside, which was transformed, via selective reduction of the azide group, coupling with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the end product.(Ref. 3062)


Fatty acid 18:0

LCB d18:1
567
GM3 analog
9-methoxy-NeuAc2-3Galb1-4GlcCer
GSG3070
Hideharu Ishida
C60H110N2O21 1195.516 Download ChemDraw structure file
C-9-Methylation in the neuraminic acid of GM3 does not impair the ability of trypanosoma crusi trans-sialidase to donate the modified sialic acid.. (Ref. 3070)
-0.7deg(Ref. 3062)
1D 1H-NMR (Ref. 3062)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside with the methylthio glycoside of 9-methoxy-NeuAc gave the corresponding 2-(trimethylsilyl)ethyl sialyl a(2-3')-b-lactoside, which were converted, via O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the sialyl a(2-3')-lactose trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor afforded the corresponding b-glycoside, which was transformed, via selective reduction of the azide group, coupling with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the end product.(Ref. 3062)


Fatty acid 18:0

LCB d18:1
568
GM3 analog
9-deoxy-NeuAc2-3Galb1-4GlcCer
GSG3071
Hideharu Ishida
C60H110N2O20 1179.517 Download ChemDraw structure file
9-Deoxy-GM3 evidenced the reduced immunosuppressive activity compared with GM3 with an unmodified sialic acid.(Ref. 3002)
C-9-Deoxygenation in the neuraminic acid of GM3 does not impair the ability of trypanosoma crusi trans-sialidase to donate the modified sialic acid.. (Ref. 3070)
-0.5deg(Ref. 3063)
1D 1H-NMR (Ref. 3063)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside with the methylthio glycoside of 9-deoxy-NeuAc gave the corresponding 2-(trimethylsilyl)ethyl sialyl a(2-3')-b-lactoside, which were converted, via O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the sialyl a(2-3')-lactose trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor afforded the corresponding b-glycoside, which was transformed, via selective reduction of the azide group, coupling with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the end product.(Ref. 3063)


Fatty acid 18:0

LCB d18:1
569
GM3 analog
4-deoxy-NeuAc2-3Galb1-4GlcCer
GSG3072
Hideharu Ishida
C60H110N2O20 1179.517 Download ChemDraw structure file
C-4-Deoxygenation in the neuraminic acid of GM3 impair the ability of trypanosoma crusi trans-sialidase to donate the modified sialic acid (Ref. 3070)
-14.0deg(Ref. 3063)
1D 1H-NMR (Ref. 3063)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside with the methylthio glycoside of 4-deoxy-NeuAc gave the corresponding 2-(trimethylsilyl)ethyl sialyl a(2-3')-b-lactoside, which were converted, via O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the sialyl a(2-3')-lactose trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor afforded the corresponding b-glycoside, which was transformed, via selective reduction of the azide group, coupling with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the end product.(Ref. 3063)


Fatty acid 18:0

LCB d18:1
570
GM3 analog
7-deoxy-NeuAc2-3Galb1-4GlcCer
GSG3073
Hideharu Ishida
C60H110N2O20 1179.517 Download ChemDraw structure file
C-7-Deoxygenation in the neuraminic acid of GM3 impair the ability of trypanosoma crusi trans-sialidase to donate the modified sialic acid. (Ref. 3070)
-9.2deg(Ref. 3063)
1D 1H-NMR (Ref. 3063)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside with the methylthio glycoside of 7-deoxy-NeuAc gave the corresponding 2-(trimethylsilyl)ethyl sialyl a(2-3')-b-lactoside, which were converted, via O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the sialyl a(2-3')-lactose trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor afforded the corresponding b-glycoside, which was transformed, via selective reduction of the azide group, coupling with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the end product.(Ref. 3063)


Fatty acid 18:0

LCB d18:1
571
GM3 analog
8-deoxy-NeuAc2-3Galb1-4GlcCer
GSG3074
Hideharu Ishida
C60H110N2O20 1179.517 Download ChemDraw structure file
C-8-Deoxygenation in the neuraminic acid of GM3 impair the ability of trypanosoma crusi trans-sialidase to donate the modified sialic acid (Ref. 3070)
-1.2deg(Ref. 3063)
1D 1H-NMR (Ref. 3063)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside with the methylthio glycoside of 8-deoxy-NeuAc gave the corresponding 2-(trimethylsilyl)ethyl sialyl a(2-3')-b-lactoside, which were converted, via O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the sialyl a(2-3')-lactose trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor afforded the corresponding b-glycoside, which was transformed, via selective reduction of the azide group, coupling with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the end product.(Ref. 3063)


Fatty acid 18:0

LCB d18:1
572
sialyl-Lex analog
C8-NeuAc2-3Galb1-4(Fuca1-3)GlcNAcb1-3GalCer
GSG3075
Hideharu Ishida
C72H129N3O29 1500.797 Download ChemDraw structure file
The modification, shortening the glycerol side chain, in the sialic acid of the sLex was tolerated by all three selectins. (Ref. 3071)
-28.1deg(Ref. 3064)
1D 1H-NMR (Ref. 3064)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl 6-O-benzoyl-b-D-galactopyranoside with the phenyl 2-thioglycoside derivative of C8-NeuAc gave the required 2-(trimethylsilyl)ethyl sialyl-(2-3)-b-galactopyranoside, which was converted into the corresponding methyl thio glycoside as the glycosyl donor. Glycosylation of the suitbly protected Fuc-(1-3)-O-GlcNAc-(1-3)-Gal trisaccharide with the donor in the presence of DMTST afforded the expected b-glycoside, which was converted into the corresponding a-trichloroacetimidate, which, on coupling with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycoside. Finally, these were transformed, via selective reduction of the azide group, condensation with octadecanoic acid, O-deacylation, and de-esterification into the target compound.(Ref. 3064)


Fatty acid 18:0

LCB d18:1
573
sialyl-Lex analog
8-epi-NeuAc2-3Galb1-4(Fuca1-3)GlcNAcb1-3GalCer
GSG3076
Hideharu Ishida
C73H131N3O30 1530.823 Download ChemDraw structure file
The modification, epimerization at C-8, in the sialic acid of the sLex was tolerated by all three selectins. (Ref. 3071)
-20.0deg(Ref. 3064)
1D 1H-NMR (Ref. 3064)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl 6-O-benzoyl-b-D-galactopyranoside with the methyl 2-thioglycoside derivative of 8-epi-NeuAc gave the required 2-(trimethylsilyl)ethyl sialyl-(2-3)-b-galactopyranoside, which was converted into the corresponding methyl thio glycoside as the glycosyl donor. Glycosylation of the suitbly protected Fuc-(1-3)-O-GlcNAc-(1-3)-Gal trisaccharide with the donor in the presence of DMTST afforded the expected b-glycoside, which was converted into the corresponding a-trichloroacetimidate, which, on coupling with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycoside. Finally, these were transformed, via selective reduction of the azide group, condensation with octadecanoic acid, O-deacylation, and de-esterification into the target compound.(Ref. 3064)


Fatty acid 18:0

LCB d18:1
574
sialyl-Lex analog
C7-NeuAc2-3Galb1-4(Fuca1-3)GlcNAcb1-3GalCer
GSG3077
Hideharu Ishida
C71H127N3O28 1470.771 Download ChemDraw structure file

-17.8deg(Ref. 3064)
1D 1H-NMR (Ref. 3064)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl 6-O-benzoyl-b-D-galactopyranoside with the phenyl 2-thioglycoside derivative of C7-NeuAc gave the required 2-(trimethylsilyl)ethyl sialyl-(2-3)-b-galactopyranoside, which was converted into the corresponding methyl thio glycoside as the glycosyl donor. Glycosylation of the suitbly protected Fuc-(1-3)-O-GlcNAc-(1-3)-Gal trisaccharide with the donor in the presence of DMTST afforded the expected b-glycoside, which was converted into the corresponding a-trichloroacetimidate, which, on coupling with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycoside. Finally, these were transformed, via selective reduction of the azide group, condensation with octadecanoic acid, O-deacylation, and de-esterification into the target compound.(Ref. 3064)


Fatty acid 18:0

LCB d18:1
575
sialyl-Lex analog
NeuAc2-3Galb1-4(2-deoxy-Fuca1-3)GlcNAcb1-3GalCer
GSG3078
Hideharu Ishida
C73H131N3O29 1514.824 Download ChemDraw structure file
Removal of oxygen at the C-2 position of the fucose residue of sLex completely eliminated recognition by E- and L-selectin. P-selectin, however , was able to recognize this structure.(Ref. 3071)
-5.3deg(Ref. 3065)
1D 1H-NMR (Ref. 3065)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-benzyl-b-D-galactopyranoside with the methyl 1-thioglycoside derivative of 2-deoxyfucose gave the required trisaccharide. This transformed into the glycosyl acceptor. DMTST promoted glycosylation of the trisaccharide acceptor with NeuAc-(2-3)-Gal donor afforded the desired pentasaccharide, which was converted into the corresponding a-trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor afforded the expected b-glycoside, which was transformed, via selective reduction of the azido group, coupling with octadecanoic acid, O-deacylation, and de-esterification, into the target compound.(Ref. 3065)


Fatty acid 18:0

LCB d18:1
576
sialyl-Lex analog
NeuAc2-3Galb1-4(3-deoxy-Fuca1-3)GlcNAcb1-3GalCer
GSG3079
Hideharu Ishida
C73H131N3O29 1514.824 Download ChemDraw structure file
Removal of oxygen at the C-3 position of the fucose residue of sLex completely eliminated recognition by all three selectins.(Ref. 3071)
-5.4deg(Ref. 3065)
1D 1H-NMR (Ref. 3065)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-benzyl-b-D-galactopyranoside with the methyl 1-thioglycoside derivative of 3-deoxyfucose gave the required trisaccharide. This transformed into the glycosyl acceptor. DMTST promoted glycosylation of the trisaccharide acceptor with NeuAc-(2-3)-Gal donor afforded the desired pentasaccharide, which was converted into the corresponding a-trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor afforded the expected b-glycoside, which was transformed, via selective reduction of the azido group, coupling with octadecanoic acid, O-deacylation, and de-esterification, into the target compound.(Ref. 3065)


Fatty acid 18:0

LCB d18:1
577
sialyl-Lex analog
NeuAc2-3Galb1-4(4-deoxy-Fuca1-3)GlcNAcb1-3GalCer
GSG3080
Hideharu Ishida
C73H131N3O29 1514.824 Download ChemDraw structure file
Removal of oxygen at the C-4 position of the fucose residue of sLex completely eliminated recognition by E- and L-selectin. P-selectin, however , was able to recognize this structure.(Ref. 3071)
-13.5deg(Ref. 3065)
1D 1H-NMR (Ref. 3065)



Chemical Synthesis
Glycosylation of 2-(trimethylsilyl)ethyl O-(2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-benzyl-b-D-galactopyranoside with the methyl 1-thioglycoside derivative of 4-deoxyfucose gave the required trisaccharide. This transformed into the glycosyl acceptor. DMTST promoted glycosylation of the trisaccharide acceptor with NeuAc-(2-3)-Gal donor afforded the desired pentasaccharide, which was converted into the corresponding a-trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor afforded the expected b-glycoside, which was transformed, via selective reduction of the azido group, coupling with octadecanoic acid, O-deacylation, and de-esterification, into the target compound.(Ref. 3065)


Fatty acid 18:0

LCB d18:1
578
Glucronosyla1-1ceramide
GSG6001
Nagatoshi Fujiwara
Download ChemDraw structure file
Stimulation of phagocytosis and phagosome-lysosome fusion(Ref. 6005)
Induction of apoptosis in HL-60 cell
Chloroform/methanol(2:1, v/v)

FAB-MS(-),[M-H]-=742,702(2OH-C14:0-dDC21:0,2OH-C14:0-dC18:0)(Ref. 6004)
[Spectrum 6001]

TLC with developing solvent Chloroform/methanol/acetic acid/water(100:20:12:5, by vol.) or Chloroform/methanol/water(65:25:4, by vol.)(Ref. 6006)
[Chromatogram 6001]
GC of alditol acetate derivatives(Ref. 6004)
[Chromatogram 6003]
Sphingomonas species(Ref. 6004) Flavobacterium devorans ATCC 10829 (Ref. 1392)



Fatty acid 2OH-C14:0

LCB dD21:0, d18:0
579
Glucosaminyla1-4glucuronosyla1-1ceramide
GSG6002
Nagatoshi Fujiwara
Download ChemDraw structure file

Chloroform/methanol(2:1, v/v)

FAB-MS(-),[M-H]-=903,863,945(2OH-C14:0-dDC21:0,2OH-C14:0-dC18:0)(Ref. 6004)
[Spectrum 6003]

Two-dimensional TLC with developing solvent 1st; Chloroform/methanol/water(65:25:4, by vol.), 2nd; Chloroform/methanol/water(65:25:10, by vol.)(Ref. 6004)
[Chromatogram 6002]
GC of alditol acetate derivatives(Ref. 6004)
[Chromatogram 6003]
Sphingomonas species(Ref. 6004)



Fatty acid 2OH-C14:0

LCB dD21:0, d18:0
580
Galactosyla1-6glucosaminyla1-4glucuronosyla1-1ceramide
GSG6003
Nagatoshi Fujiwara
Download ChemDraw structure file

Chloroform/methanol(2:1, v/v)

FAB-MS(-),[M-H]-=1065,1025,1107(2OH-C14:0-dDC21:0,2OH-C14:0-dC18:0)(Ref. 6004)
[Spectrum 6004]

Two-dimensional TLC with developing solvent 1st; Chloroform/methanol/water(65:25:4, by vol.), 2nd; Chloroform/methanol/water(65:25:10, by vol.)(Ref. 6004)
[Chromatogram 6002]
GC of alditol acetate derivatives(Ref. 6004)
[Chromatogram 6003]
Sphingomonas species(Ref. 6004)



Fatty acid 2OH-C14:0

LCB dD21:0, d18:0
581
Mannosyla1-2Galactosyla1-6glucosaminyla1-4glucuronosyla1-1ceramide
GSG6004
Nagatoshi Fujiwara
Download ChemDraw structure file
Stimulation of phagocytosis and phagosome-lysosome fusion(Ref. 6005)
Induction of apoptosis in HL-60 cell
Chloroform/methanol(1:4, v/v)
1H NMR and 13C NMR(Ref. 6003)
[Table 6001]
FAB-MS(-),[M-H]-=1227,1187,1269(2OH-C14:0-dDC21:0,2OH-C14:0-dC18:0)(Ref. 6004)
[Spectrum 6005]

Two-dimensional TLC with developing solvent 1st; Chloroform/methanol/water(65:25:4, by vol.), 2nd; Chloroform/methanol/water(65:25:10, by vol.)(Ref. 6004)
[Chromatogram 6002]
GC of alditol acetate derivatives(Ref. 6004)
[Chromatogram 6003]
Sphingomonas species(Ref. 6004)



Fatty acid 2OH-C14:0

LCB dD21:0, d18:0

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TITLE:Identification of a major carbohydrate capping group of the L-selectin ligand on high endothelial venules in human lymph nodes as 6-sulfo sialyl Lewis X PubMed ID:9556613
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[3055]
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[3056]
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