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Ether type lipid

(total 547)
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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
archaetidic acid/diether analog of phosphatidic acid(Ref. 0001)
2,3-di-O-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol-1-phosphate/ 2,3-di-O-phytanyl-sn-glycerol-1-phosphate(Ref. 0001)
EEL0001
Yosuke Koga
C43H89O6P 733.137

-CH2-, 2830-2960, 1460, 1375cm-1; -CH(CH3)2, 1360cm-1; ether C-O-C, 1110 cm-1; P=O, P-0, P-O-C, 1210, 1100, 1050cm-1(Ref. 0001)
31P-NMR: 0.92 ppm (pH1.6); 1.47 ppm (pH3.8); 2.07 ppm (pH7.5); 5.38 ppm (pH10.1); 5.63 ppm (pH12.8) (Ref. 0001)spectrum :
[Spectrum 0001]
FAB m/z 733.8 (M+1)+

TLC chloroform-methanol-14M aqueous ammonia (60:35:8) Rf=0.41; chloroform-methanol-acetic acid-water (85:30:15:5) Rf=0.85(Ref. 0001)
Methanobacterium thermoautotrophicum(Ref. 0001)/Natronobacterium sp. from India(Ref. 0030)



2
caldarchaetidic acid/tetraether analog of phosphatidic acid(Ref. 0001)
EEL0002
Yosuke Koga
C86H173O9P 1382.262

-OH, 3400, 1040cm-1; -CH2-, 2830-2960, 1460, 1375cm-1; ether C-O-C, 1110 cm-1; P=O, P-0, P-O-C, 1210, 1100, 1050cm-1; absence of -CH(CH3)2, 1360cm-1(Ref. 0001)
31P-NMR: 0.92 ppm (pH1.6); 1.36 ppm (pH3.8); 2.05ppm (pH7.5); 5.30ppm (pH10.1); 5.66ppm (pH12.8)(Ref. 0001)
FAB m/z 1381.9 (M+1)+

TLC chloroform-methanol-14M aqueous ammonia (60:35:8) Rf=0.45; chloroform-methanol-acetic acid-water (85:30:15:5) Rf=0.88(Ref. 0001)
Methanobacterium thermoautotrophicum(Ref. 0001)




3
glucosyl archaeol(Ref. 0002)
1-b-D-glucopyranosyl-2,3-di-O-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol/ 1-b-D-glucopyranosyl-2,3-di-O-phytanylglycerol(Ref. 0002)
EEL0003
Yosuke Koga
Glc ArOH(Ref. 0002)
C49H98O8 815.298

[a]D = -11.30; MD = -91.98(Ref. 0002)
13C-NMR, 68.84 (C-1 of sn-2 phytanyl chain), 70.18 (C-1 of sn-3 phytanyl chain), 69.42 (C-1 of glycerol), 78.39 (C-2 of glycerol), 70.84 (C-3 of glycerol), 103.87 (C-1 of sugar), 74.10 (C-2 of sugar), 76.90 (C-3 of sugar), 70.38 (C-4 of sugar), 76.68 (C-5 of sugar), 61.82 (C-6 of sugar)(Ref. 0002)


TLC chloroform-methanol-acetic acid-water (85:22.5:10:4) Rf=0.95(Ref. 0002)chromatogram :
[Chromatogram 0001]
Methanococcus voltae(Ref. 0002)




4
b-hydroxyarchaetidylserine(Ref. 0003)
2,3-di-O-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol-1-phosphoserine/ 2,3-di-O-phytanyl-sn-glycerol-1-phosphoserine(Ref. 0003)
EEL0004
Yosuke Koga
b-OH-AS(Ref. 0003)
C46H94O9NP 836.214


positive FAB m/z 858 (M+Na) (Ref. 0003)

TLC, chloroform-methanol-conc-aqueous ammonia (65:35:8) Rf=0.37; chloroform-methanol-acetic acid-water (80:30:15:5) Rf=0.38(Ref. 0003)chromatogram :
[Chromatogram 0002] (Ref. 0003)
Methanosarcina barkeri(Ref. 0003)




5
b-hydroxyarchaetidyl-myo-inositol(Ref. 0003)
2-O-(3'-hydroxy-3',7',11',15'-tetramethyl)hexadecyl-3-O-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol-1-phospho-myo-inositol
EEL0005
Yosuke Koga
b-OH-AI(Ref. 0003)
C49H99O12P 911.277


positive FAB m/z 933 (M+Na)

TLC, chloroform-methanol-conc-aqueous ammonia (65:35:8) Rf=0.34; chloroform-methanol-acetic acid-water (80:30:15:5) Rf=0.30(Ref. 0003)chromatogram :
[Chromatogram 0002] (Ref. 0003)
Methanosarcina barkeri(Ref. 0003)




6
archaetidyl(glucosaminyl)-myo-inositol(Ref. 0009)
2,3-di-O-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol-1-phospho-1''-[6''-O-(2'''-amino-deoxy-a-D-glucopyranosyl)]-1''-D-myo-inositol/2,3-di-O-phytanyl-sn-glycerol-1-phospho(glucosaminyl)-myo-inositol(Ref. 0009)
EEL0006
Yosuke Koga
Ar(GlcN)I(Ref. 0009)
C55H110NO15P 1056.433

-CH3 and -CH2-, 2840-2950, 1465, 1375cm-1; -CH(CH3)2, 1360cm-1; ether C-O-C, 1110 cm-1; P=O, P-O, P-O-C, 1220, 1100, 1050cm-1; -NH2, 3390, 1640, 1560cm-1; -OH, 3400cm-1;(Ref. 0009)
positive FAB m/z 1056 (m+1),

chromatogram :
[Chromatogram 0002] (Ref. 0003)
Methanosarcina barkeri(Ref. 0009)




7
b-hydroxyarchaetidylglycerol(Ref. 0010)
2-O-(3'-hydroxy-3',7',11',15'-tetramethyl)hexadecyl)-3-O-(3'',7'',11'',15''-tetramethyl)hexadecyl-sn-glycerol-1-phospho-3'''-sn-glycerol/ 2-O-(3'-hydroxy)phytanyl-3-O-phytanyl-sn-glycerol-1-phospho-3''-sn-glycerol
EEL0007
Yosuke Koga
b-OH-AG(Ref. 0010)
C46H95O9P 823.215


positive FAB m/z 845 (M+H+Na), 867 (M+2Na)spectrum :
[Spectrum 0004] (Ref. 0010)

TLC, chloroform-methanol-acetic acid-water (90:30:15:4) Rf=0.64; chloroform-methanol-conc-aqueous ammonia (65:35:8) Rf=0.67(Ref. 0010)chromatogram :
[Chromatogram 0002] (Ref. 0003)
Methanosarcina barkeri(Ref. 0010)




8
b-hydroxyarchaetidylethanolamine(Ref. 0010)
2-O-(3'-hydroxy-3',7',11',15'-tetramethyl)hexadecyl-3-O-(3'',7'',11'',15''-tetramethyl)hexadecyl-sn-glycerol-1-phosphoethanolamine/ 2-O-(3'-hydroxy)phytanyl-3-O-phytanyl-sn-glycerol-1-phosphoethanolamine
EEL0008
Yosuke Koga
b-OH-AE(Ref. 0010)
C45H94O7NP 792.204


positive FAB m/z 792 (M+H)spectrum :
[Spectrum 0004] (Ref. 0010)

TLC, chloroform-methanol-acetic acid-water (90:30:15:4) Rf=0.74; chloroform-methanol-conc-aqueous ammonia (65:35:8) Rf=0.72(Ref. 0010)chromatogram :
[Chromatogram 0002] (Ref. 0003)
Methanosarcina barkeri(Ref. 0010)




9
b-hydroxyarchaeol(Ref. 0003)
2-O-(3'-hydroxy-3',7',11',15'-tetramethyl)hexadecyl-3-O-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol/ 2-O-(3'-hydroxy)phytanyl-3-O-phytanyl-sn-glycerol
EEL0009
Yosuke Koga
b-OH-ArOH(Ref. 0003)
C43H88O4 669.156

[a]D=+5.65 degree
13C-NMR, 67.49 (C1 sn-2), 70.23 (C1 sn-3), 39.97 (C2 sn-2), 36.59 (C2 sn-3), 72.47 (C3 sn-2), 29.92 (C3 sn-3), 43.12 (C4 sn-2), 37.31-37.48 (C4 sn-3), 21.49 (C5 sn-2), 24.39 (C5 sn-3), 26.66 (C17 sn-2), 19.76-19.71 (C17 sn-3). Carbon numbers of the hydrocarbon chains are shown.
positive FAB m/z 691 ([M+Na]); GC-MS of acetylated derivative m/z 397 (M-OC20H40OCOCH3), m/z 355 (OC20H40OCOCH3)

TLC, light petroleum-ethyl ether-acetic acid (50:50:1) Rf=0.19 (Ref. 0003)chromatogram:
[Chromatogram 0003](Ref. 0003)
Methanosarcina barkeri(Ref. 0003), Methanosarcina mazei(Ref. 0011), Methanococcus vannielii(Ref. 0121), Methanococcus voltae(Ref. 0121), Methanolobus tindarius(Ref. 0121), Methanohalophilus mahii(Ref. 0121)




10
b-methoxyarchaeol(Ref. 0011)
2-O-(3'-methoxy-3',7',11',15'-tetramethyl)hexadecyl-3-O-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol/ 2-O-(3'-methoxy)phytanyl-3-O-phytanyl-sn-glycerol
EEL0010
Yosuke Koga
b-Me-OH-ArOH(Ref. 0011)
C44H90O4 683.183



Methanosarcina barkeri (methanolysis by-product)(Ref. 0011), Methanosarcina mazei (methanolysis by-product)(Ref. 0011)




11
b-hydroxyarchaeol methyl ether(Ref. 0011)
1-O-methyl-2-O-(3'-hydroxy-3',7',11',15'-tetramethyl)hexadecyl-3-O-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol/ 1-O-methyl-2-O-(3'-hydroxy)phytanyl-3-O-phytanyl-sn-glycerol
EEL0011
Yosuke Koga
b-OH-ArO-Me(Ref. 0011)
C44H90O4 683.183




Methanosarcina barkeri (methanolysis by-product) (Ref. 0011)




12
b-methoxyarchaeol methyl ether(Ref. 0011)
1-O-methyl-2-O-(3'-methoxy-3',7',11',15'-tetramethyl)hexadecyl-3-O-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol/ 1-O-methyl-2-O-(3'-methoxy)phytanyl-3-O-phytanyl-sn-glycerol
EEL0012
Yosuke Koga
DMe-OH-ArOH(Ref. 0011)
C45H92O4 697.210




Methanosarcina barkeri (methanolysis by-product)(Ref. 0011)




13
3-O-monophytanyl-sn-glycerol(Ref. 0011)
3-O-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol
EEL0013
Yosuke Koga
3-MAGro(Ref. 0011)
C23H48O3 372.625




Methanosarcina barkeri (methanolysis by-product) (Ref. 0011)




14
glucosyl-galactosyl caldarchaetidyltrimethyl aminopentanetetrol(Ref. 0014)
D-glucopyranosyl(a1-2)b-D-galactofuranosyl caldarchaetidyl-N,N,N-trimethyl aminopentanetetrol
EEL0014
Yosuke Koga
Glc-Gal-CATMAPT/PGL III (Ref. 0014)
C106H212O23NP 1899.784

13C-NMR, 107.26 (C1 of Gal), 89.32 (C2 of Gal), 76.79(C3 of Gal), 83.39(C4 of Gal), 71.85 (C5 of Gal), 64.66 (C6of Gal), 99.79 (C1 of Glc), 72.93 (C2 of Glc), 74.60 (C3 of Glc), 71.60 (C4 of Glc), 73.79 (C5 of Glc), 62.73 (C6 of Glc), 67.83 (C1 of TMAPT), 72.35 (C2 of TMAPT), 73.52 (C3 of TMAPT), 73.22 (C4 of TMAPT), 64.66 (C5 of TMAPT), 54.33 (N-CH3of TMAPT), 67.87 (C1 of Gro), 78.68 (C2 of Gro), 71.88 (C3 of Gro), 65.92 (C1 of Gro), 78.95 (C2 of Gro), 71.49 (C3of Gro) (Ref. 0014)

chromatogram:
[Chromatogram 0006] (Ref. 0014)
Methanospirillum hungatei(Ref. 0014)




15
galactosyl-galactosyl caldarchaetidyltrimethyl aminopentanetetrol(Ref. 0014)
D-galctofuranosyl(b1-6)b-D-galactofuranosyl caldarchaetidyl-N,N,N-trimethyl aminopentanetetrol
EEL0015
Yosuke Koga
Gal-Gal-CATMAPT/PGL IV (Ref. 0014)
C106H212O23NP 1899.784

13C-NMR, 109.25 (C1 of Gal), 81.92 (C2 of Gal), 79.06(C3 of Gal), 86.07(C4 of Gal), 70.97 (C5 of Gal), 70.42 (C6 of Gal), 109.68 (C1 of Gal), 81.92 (C2 of Gal), 79.06 (C3 of Gal), 85.51 (C4 of Gal), 72.12 (C5 of Gal), 64.03 (C6 of Gal), 67.72 (C1 of TMAPT), 62.33 (C2 of TMAPT), 73.47 (C3 of TMAPT), 73.19 (C4 of TMAPT), 64.6 (C5 of TMAPT), 54.21 (N-CH3 of TMAPT), 67.72 (C1 of Gro), 78.55(C2 of Gro), 71.69 (C3 of Gro), 65.87 (C1 of Gro), 78.90(C2 of Gro), 71.86 (C3of Gro) (Ref. 0014)

chromatogram:
[Chromatogram 0006] (Ref. 0014)
Methanospirillum hungatei(Ref. 0014)




16
glucosyl-galactosyl caldarchaetidyldimethyl aminopentanetetrol(Ref. 0014)
D-glucopyranosyl(a1-2)b-D-galactofuranosyl caldarchaetidyl-N,N-dimethyl aminopentanetetrol
EEL0016
Yosuke Koga
Glc-Gal-CADMAPT/PGL VI (Ref. 0014)
C105H208O22NP 1867.742

13C-NMR, 107.19 (C1 of Gal), 89.11 (C2 of Gal), 76.81(C3 of Gal), 83.57 (C4 of Gal), 71.7 (C5 of Gal), 64.69 (C6of Gal), 99.70 (C1 of Glc), 72.85 (C2 of Glc), 74.55 (C3 of Glc), 71.61 (C4 of Glc), 73.78 (C5 of Glc), 62.77 (C6 of Glc), 60.48 (C1 of DMAPT), 72.05 (C2 of DMAPT), 73.20 (C3 of DMAPT), 72.85 (C4 of DMAPT), 64.37(C5 of DMAPT), 42.42,44.85 (N-CH3 of DMAPT), 67.83 (C1 of Gro), 78.63 (C2 of Gro), 71.86 (C3 of Gro), 66.30(C1 of Gro), 78.87 (C2 of Gro), 71.61C3of Gro) (Ref. 0014)

chromatogram:
[Chromatogram 0006] (Ref. 0014)
Methanospirillum hungatei(Ref. 0014)




17
galactosyl-galactosyl caldarchaetidyl dimethylaminopentanetetrol(Ref. 0014)
D-galactofuranosyl(b1-6)b-D-galactofuranosyl caldarchaetidyldimethyl aminopentanetetrol
EEL0017
Yosuke Koga
Gal-Gal-CADMAPT/PGL VI I (Ref. 0014)
C105H208O22NP 1867.742

13C-NMR, 109.22 (C1 of Gal), 81.76 (C2 of Gal), 79.08 (C3 of Gal), 86.21 (C4 of Gal), 70.94 (C5 of Gal), 70.41 (C6 of Gal), 109.66(C1 of Gal), 81.76 (C2 of Gal), 79.08 (C3 of Gal), 85.59 (C4 of Gal), 72.09 (C5 of Gal), 64.03 (C6 of Gal), 60.60 (C1 of DMAPT), 71.81 (C2 of DMAPT), 73.40(C3 of DMAPT), 72.75 (C4 of DMAPT), 64.26 (C5 of DMAPT), 43.2 (N-CH3 of DMAPT), 67.67 (C1 of Gro), 78.50(C2 of Gro), 71.55 (C3 of Gro), 66.19 (C1 of Gro), 78.80(C2 of Gro), 71.55 (C3 of Gro) (Ref. 0014)

chromatogram:
[Chromatogram 0006] (Ref. 0014)
Methanospirillum hungatei (Ref. 0014)




18
glucosyl-galactosyl-(galactosyl) caldarchaeol(Ref. 0014)
1-D-glucopyranosyl(a1-2)-b-D-galactofuranosyl-(1'-b-D-galactofuranosyl) caldarchaeol
EEL0018
Yosuke Koga
Glc-Gal-(Gal)-CA/TGT-I (Ref. 0014)
C104H202O21 1788.704

13C-NMR, 107.16 (C1 of Gal), 89.28 (C2 of Gal), 76.75(C3 of Gal), 83.51 (C4 of Gal), 71.65 (C5 of Gal), 64.54 (C6 of Gal), 99.71 (C1 of Glc), 72.82 (C2 of Glc), 74.59(C3 of Glc), 71.65 (C4 of Glc), 73.68 (C5 of Glc), 62.76 (C6 of Glc), 109.13 (C1 of Gal), 81.55 (C2 of Gal), 73.96 (C3 of Gal), 85.86 (C4 of Gal), 72.11 (C5 of Gal), 64.25 (C6 of Gal), 67.79 (C1 of Gro), 78.57 (C2 of Gro), 71.65 (C3 of Gro), 67.46 (C1 of Gro), 78.45 (C2 of Gro), 71.65C3of Gro)(Ref. 0014)


chromatogram:
[Chromatogram 0006](Ref. 0014)
Methanospirillum hungatei(Ref. 0014)




19
glucosyl-6-acetylgalactosyl-caldarchaeol(Ref. 0014)
D-glucopyranosyl(a1-2)-6-acetyl-b-D-galactofuranosyl caldarchaeol
EEL0019
Yosuke Koga
Glc-6-AcGal-CAOH /Ac-DGT-I(Ref. 0014)
C100H194O17 1668.600

13C-NMR, 107.17 (C1 of Gal), 89.08 (C2 of Gal), 76.47 (C3 of Gal), 83.26 (C4 of Gal), 68.42 (C5 of Gal), 66.34 (C6 of Gal), 99.78 (C1 of Glc), 72.72 (C2 of Glc), 74.84 (C3 of Glc), 71.66 (C4 of Glc), 73.58 (C5 of Glc), 62.73 (C6 of Glc), 67.84 (C1 of Gro), 78.46 (C2 of Gro), 71.66 (C3 of Gro), 62.64 (C1 of Gro), 79.87 (C2 of Gro), 71.66C3of Gro) (Ref. 0014)


chromatogram:
[Chromatogram 0006] (Ref. 0014)
Methanospirillum hungatei(Ref. 0014)




20
glucosyl-6-acetylgalactosyl-archaeol(Ref. 0014)
D-glucopyranosyl(a1-2)-6-acetyl-b-D-galactofuranosyl archaeol
EEL0020
Yosuke Koga
Glc-6-AcGal-ArOH /Ac-DGD-I(Ref. 0014)
C57H110O14 1019.475

13C-NMR, 107.33 (C1 of Gal), 89.22 (C2 of Gal), 76.55 (C3 of Gal), 83.23 (C4 of Gal), 68.45 (C5 of Gal), 66.51 (C6 of Gal), 99.71 (C1 of Glc), 72.85 (C2 of Glc), 74.54 (C3 of Glc), 71.62 (C4 of Glc), 73.70(C5 of Glc), 62.74 (C6 of Glc), 67.96 (C1 of Gro), 78.56 (C2 of Gro), 71.62 (C3 of Gro)(Ref. 0014)


chromatogram:
[Chromatogram 0006](Ref. 0014)
Methanospirillum hungatei(Ref. 0014)




21
caldarchaetidylglycerol(Ref. 0014)
EEL0021
Yosuke Koga
CAG/TsPG(Ref. 0014) A1-1
C89H179O11P 1456.341

liquid SIMS 1454.8(M-H)- (Ref. 0168)

HPLC-Evaporative Light-Scattering Detection (Ref. 0168), HPTLC (Ref. 0168)
Methanospirillum hungatei(Ref. 0014) / Thermoplasma acidophilum (Ref. 0168)




22
galactosyl-galactosyl a-hydroxyarchaeol(Ref. 0016)
1-D-galactopyranosyl(b1-6)-b-D-galactopyranosyl 2-O-(3',7',11',15'-tetramethyl)hexadecyl-3-O-(3'-hydroxy-3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol/ 1-D-galactopyranosyl(b1-6)-b-D-galactopyranosyl 2-O-phytanyl-3-O-(3'-hydroxy)phytanyl-sn-glycerol
EEL0022
Yosuke Koga
Gal-Gal-a-OH-ArOH/GL-1(Ref. 0016)
C55H108O14 993.438

13C-NMR, 104.73 (C1 of Gal), 71.96 (C2 of Gal), 74.00 (C3 of Gal), 68.89 (C4 of Gal), 74.14 (C5 of Gal), 68.45 (C6 of Gal), 104.56 (C1' of Gal), 71.96 (C2' of Gal), 74.28 (C3' of Gal), 69.75 (C4' of Gal), 75.82 (C5' of Gal), 62.22 (C6' of Gal), 69.45 (C1 of Gro), 78.39 (C2 of Gro), 71.40 (C3 of Gro), 69.10 (C1 of sn-3 phytanyl), 68.89 (C1 of sn-2 phytanyl)(Ref. 0016), 1H-NMR(Ref. 0016)

TLC, chloroform-methanol-acetic acid-water (85:22.5:10:4) Rf 0.46chromatogram:
[Chromatogram 0007] (Ref. 0016)
Methanosaeta concilii(Ref. 0016)




23
mannosyl-galactosyl archaeol(Ref. 0016)
1-D-mannopyranosyl(a1-3)-b-D-galactopyranosyl 2,3-di-O-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol/ 1-D-mannopyranosyl(a1-3)-b-D-galactopyranosyl-2,3-di-O-phytanyl-sn-glycerol
EEL0023
Yosuke Koga
Man-Gal-ArOH/GL-2(Ref. 0016)
C55H108O13 977.438

13C-NMR, 104.77 (C1 of Gal), 70.25 (C2 of Gal), 77.51(C3 of Gal), 65.28 (C4 of Gal), 75.33 (C5 of Gal), 61.83 (C6 of Gal), 97.11 (C1' of Man), 71.56 (C2' of Man), 71.94 (C3' of Man), 67.98 (C4' of Man), 73.61 (C5' of Man), 62.26 (C6' of Man), 69.74 (C1 of Gro), 78.66 (C2 of Gro), 71.49 (C3 of Gro), 70.40 (C1 of sn-3 phytanyl), 69.11 (C1 of sn-2 phytanyl)(Ref. 0016), 1H-NMR(Ref. 0016)

TLC, chloroform-methanol-acetic acid-water (85:22.5:10:4) Rf 0.50chromatogram:
[Chromatogram 0007](Ref. 0016)
Methanosaeta concilii(Ref. 0016)




24
a-hydroxyarchaetidylethanolamine(Ref. 0017)
2-O-(3',7',11',15'-tetramethyl)hexadecyl-3-O-(3'-hydroxy-3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol-1-phosphoethanolamine/ 2-O-phytanyl-3-O-(3'-hydroxy)phytanyl-sn-glycerol-1-phosphoethanolamine
EEL0024
Yosuke Koga
a-OH-AE/PEDOH(Ref. 0017)
C45H94O7NP 792.204

O-H, 3514cm-1; NH2, 3348, 1742, 1638, 1552cm-1; C-H, 2920, 2959, 1457cm-1; -CH(CH3)2, 1376, 1362cm-1; CH3, 2870cm-1; P=O, 1229cm-1; P-0, 1086cm-1, P-O-C, 1033cm-1(Ref. 0017)

[Spectrum 0009]A1 (13C-NMR),
[Spectrum 0009]A2 (DEPT) (Ref. 0017)13C-NMR, 65.29 (C1 of Gro), 78.38 (C2 of Gro), 70.89 (C3 of Gro), 68.83 (C1 of sn-2 phytanyl), 69.03 (C1 of sn-3 phytanyl), 40.79 (CH2-NH2), 62.79 (O-CH2), 72.39 (C3 of sn-3 phytanyl) (Ref. 0017)

[Spectrum 0008]A(Ref. 0017)positive FAB, m/z 792, 774 (M-H2O), 757 (M-H2O-NH3), 496 (M-hydroxyphytanyl)

chromatogram:
[Chromatogram 0008] (Ref. 0017)
Methanosaeta concilii(Ref. 0017)




25
galactosyl-archaeol(Ref. 0017)
b-D-galactopyranosyl 2,3-di-O-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol/b-D-galactopyranosyl-2,3-di-O-phytanyl-sn-glycerol
EEL0025
Yosuke Koga
Gal-ArOH/GalD(Ref. 0017)
C49H98O8 815.298

13C-NMR,
[Spectrum 0010]B(Ref. 0017)13C-NMR, 104.41 (C1 of Gal), 71.99 (C2 of Gal), 74.17 (C3 of Gal), 69.52 (C4 of Gal), 75.55 (C5 of Gal), 62.95 (C6 of Gal), 69.07 (C1 of Gro), 78.70 (C2 of Gro), 71.18 (C3 of Gro), 69.52 (C1 of sn-2 phytanyl), 70.39 (C1 of sn-3 phytanyl), 30.0 (C3 of sn-3 phytanyl)


chromatogram:
[Chromatogram 0008] (Ref. 0017)
Methanosaeta concilii(Ref. 0017)




26
galactosyl-a-hydroxyarchaeol(Ref. 0017)
1-b-D-galactopyranosyl 2-O-(3',7',11',15'-tetramethyl)hexadecyl-3-O-(3'-hydroxy-3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol/ 1-b-D-galactopyranosyl-2-O-phytanyl-3-O-(3'-hydroxy)phytanyl-sn-glycerol
EEL0026
Yosuke Koga
Gal-a-OH-ArOH/GalDOH(Ref. 0017)
C49H98O9 831.297

13C-NMR,
[Spectrum 0010]A2(Ref. 0017)13C-NMR, 104.41 (C1 of Gal), 71.91 (C2 of Gal), 74.23 (C3 of Gal), 69.73 (C4 of Gal), 75.69 (C5 of Gal), 62.14 (C6 of Gal), 68.81 (C1 of Gro), 78.20 (C2 of Gro), 71.99 (C3 of Gro), 69.93(C1 of sn-2 phytanyl), 69.73 (C1 of sn-3 phytanyl), 72.59 (C3 of sn-3 phytanyl)(Ref. 0017)


chromatogram:
[Chromatogram 0008] (Ref. 0017)
Methanosaeta concilii(Ref. 0017)




27
galactosyl-glucosyl-galactosyl-a-hydroxyarchaeol(Ref. 0017)
1-O-D-galactopyranosyl(b1-6)-[D-glucopyranosyl(b1-3)]-b-galactopyranosyl-2-O-(3',7',11',15'-tetramethyl)hexadecyl-3-O-(3'-hydroxy-3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol/ 1-D-galactopyranosyl(b1-6)-[D-glucopyranosyl(b1-3)]-b-galactopyranosyl-2-O-phytanyl-3-O-(3'-hydroxy)phytanyl-sn-glycerol
EEL0027
Yosuke Koga
Gal-(Glcp)-Galp-a-OH-ArOH/TGDOH(Ref. 0017)
C61H118O19 1155.578

13C-NMR,
[Spectrum 0010]C2(Ref. 0017)13C-NMR, 104.45 (C1 of Gal), 69.72 (C2 of Gal), 79.97 (C3 of Gal), 68.68 (C4 of Gal), 75.71 (C5 of Gal), 67.96 (C6 of Gal), 104.39 (C1' of 2nd Gal), 71.77 (C2' of 2nd Gal), 74.20 (C3' of 2nd Gal), 69.72 (C4' of 2nd Gal), 75.10 (C5' of 2nd Gal), 62.40 (C6' of 2nd Gal), 103.04 (C1 of Glc), 73.92 (C2 of Glc), 77.35 (C3 of Glc), 70.90 (C4 of Glc), 77.08 (C5 of Glc), 62.12 (C6 of Glc), 69.32 (C1 of Gro), 78.22 (C2 of Gro), 71.55 (C3 of Gro), 68.86 (C1 of sn-2 phytanyl), 69.03 (C1 of sn-3 phytanyl), 72.59 (C3 of sn-3 phytanyl) (Ref. 0017)


chromatogram:
[Chromatogram 0008] (Ref. 0017)
Methanosaeta concilii(Ref. 0017)




28
6-aminoethyl-phosphoryl-glucosyl-cyclic archaeol(Ref. 0019)
1-6'-aminoethyl-phosphoryl-b-D-glucopyranosyl 2,3-O-(3',7',11',15',18',22',26',30'-octamethyl)dotriacontanediyl-sn-glycerol/ 6-aminoethyl-phosphoryl-b-D-glucopyranosyl-2,3-di-O-phytanediyl-sn-glycerol
EEL0028
Yosuke Koga
6-aminoethyl-P-Glc-cycArOH/PEGlcDM(Ref. 0019)
C51H102O11NP 936.329

O-H & N-H, 3064-3500cm-1; NH2, 1726, 1637, 1534cm-1; CH3, 2887, 1378cm-1; CH2, 2956, 1471cm-1; P=O, 1235cm-1; P-O & ether C-O-C, 1098cm-1; P-O-C, 1049cm-1; absence of isopropyl doublet

[Spectrum 0011]A (Ref. 0019)13C-NMR, 69.99 (C1 of Gro), 78.59 (C2 of Gro), 71.75 (C3 of Gro), 70.27 (C1 of sn-3 alkyl), 68.93 (C1 of sn-2 alkyl), 104.47 (C1 of Glc), 74.35 (C2 of Glc), 76.89 (C3 of Glc), 69.92 (C4 of Glc), 75.92 (C5 of Glc), 65.17 (C6 of Glc)
negative FAB, m/z 934 (M - 1), 891 (M - CH2=CH-NH2), 792 (M - phosphoethanolamine), 917 (M - NH3)

chromatogram:
[Chromatogram 0009]IV (Ref. 0019)TLC, chloroform-methanol-acetic acid-water (85:22.5:10:4) Rf 0.16 (Ref. 0019)
Methanococcus jannaschii(Ref. 0019)




29
glucosyl-cyclic archaeol(Ref. 0019)
1-b-D-glucopyranosyl 2,3-O-(3',7',11',15',18',22',26',30'-octamethyl)dotriacontanediyl-sn-glycerol/ b-D-glucopyranosyl-2,3-di-O-phytanediyl-sn-glycerol
EEL0029
Yosuke Koga
Glc-cycArOH/GlcDM(Ref. 0019)
C49H96O8 813.282

[a]D = -7.67 degree/MD = -62.28 degree (Ref. 0019)
O-H, 3360cm-1; CH2, 2920, 2955, 1460cm-1; CH3, 2870cm-1; C-O-C, 1065cm-1;

[Spectrum 0011]B,
[Spectrum 0012]A (Ref. 0019)13C-NMR, 69.56 (C1 of Gro), 78.63 (C2 of Gro), 71.31 (C3 of Gro), 70.22 (C1 of sn-3 alkyl), 68.81 (C1 of sn-2 alkyl), 104.10 (C1 of Glc), 74.33 (C2 of Glc), 76.84 (C3 of Glc), 70.85 (C4 of Glc), 77.21 (C5 of Glc), 62.25 (C6 of Glc)


chromatogram:
[Chromatogram 0009] (Ref. 0019)TLC, chloroform-methanol-acetic acid-water (85:22.5:10:4) Rf 0.88 (Ref. 0019)
Methanococcus jannaschii(Ref. 0019)




30
gentiobiosyl-cyclic archaeol(Ref. 0019)
D-glucopyranosyl-(b1-6)-D-glucopyranosyl 2,3-O-(3',7',11',15',18',22',26',30'-octamethyl)dotriacontanediyl-sn-glycerol/ b-D-glucopyranosyl-(b1-6)-D-glucopyranosyl -2,3-di-O-phytanediyl-sn-glycerol
EEL0030
Yosuke Koga
Gen-cycArOH/GlcGlcDM(Ref. 0019)
C55H106O13 975.422

MD = -176.88 degree (Ref. 0019)

[Spectrum 0012]B(Ref. 0019)13C-NMR, 69.88 (C1 of Gro), 78.61 (C2 of Gro), 71.50 (C3 of Gro), 70.23 (C1 of sn-3 alkyl), 68.87 (C1 of sn-2 alkyl), 104.32 (C1 of Glc), 74.31 (C2 of Glc), 76.95 (C3 of Glc), 70.16 (C4 of Glc), 75.07 (C5 of Glc), 68.99 (C6 of Glc), 104.11 (C1' of Glc), 74.26 (C2' of Glc), 77.03 (C3' of Glc), 70.62 (C4' of Glc), 77.11 (C5' of Glc), 62.06 (C6'of Glc)


chromatogram:
[Chromatogram 0009] (Ref. 0019)TLC, chloroform-methanol-acetic acid-water (85:22.5:10:4) Rf 0.37 (Ref. 0019)
Methanococcus jannaschii(Ref. 0019)




31
cyclic archaetidylethanolamine(Ref. 0019)
2,3-O-(3',7',11',15',18',22',26',30'-octamethyl)dotriacontanediyl-sn-glycerol-1-phosphoethanolamine/ 2,3-di-O-phytanediyl-sn-glycerol-1-phosphoethanolamine
EEL0031
Yosuke Koga
cycAE/PEDM(Ref. 0019)
C45H92O6NP 774.189

N-H, 3350cm-1; NH2, 1740, 1640, 1550cm-1; P=O, 1229cm-1; P-O & ether C-O-C, 1090cm-1; P-O-C, 1030cm-1

[Spectrum 0012]C (Ref. 0019)13C-NMR, 65.85 (C1 of Gro), 78.71 (C2 of Gro), 71.57 (C3 of Gro), 70.21 (C1 of sn-3 alkyl), 68.96 (C1 of sn-2 alkyl), 40.82 (CH2-NH2)
positive FAB, m/z 776 (M + 1),

chromatogram:
[Chromatogram 0009](Ref. 0019)TLC, chloroform-methanol-acetic acid-water (85:22.5:10:4) Rf 0.48 (Ref. 0019)
Methanococcus jannaschii(Ref. 0019)




32
2,3-di-geranylgeranyl-sn-glycerol(Ref. 0020)
2,3-di-O-(3',7',11',15'-tetramethyl)hexadec-2',6',10',14'-tetraenyl-sn-glycerol
EEL0032
Yosuke Koga
DGGG/unsaturated archaeol
C43H72O3 637.030





Methanopyrus kandleri(Ref. 0020)




33
archaetidylcholine(Ref. 0021)
2,3-di-O-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol-1-phosphocholine/2,3-di-O-phytanyl-sn-glycerol-1-phosphocholine
EEL0033
Yosuke Koga
C48H101O6NP 819.292


Negative FAB, m/z 802.7 (M-H) (Ref. 0021)


Methanopyrus kandleri(Ref. 0021)




34 No image
acetyldiglycosyl archaeol(Ref. 0021)
EEL0034
Yosuke Koga
AcdiGly-ArOH(Ref. 0021)
C57H110O14 1019.475


negative FAB, m/z 1016.9 (Ref. 0021)


Methanothermus fervidus(Ref. 0021)




35 No image
acetyldiglycosyl caldarchaetidyl inositol (Ref. 0021)
EEL0035
Yosuke Koga
AcdiGly-CAI(Ref. 0021)
C106H205O25P 1910.721


negative FAB, m/z 1907.4 (Ref. 0021)


Methanothermus fervidus(Ref. 0021)




36
archaetidyl glycero(methyl)phosphate(Ref. 0022)
2,3-di-O-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol-1-phosphoglycerol-3''-(methyl)phosphate
EEL0036
Yosuke Koga
AGPMe(Ref. 0022)
C47H98O11P2 901.222

negative FAB, m/z 899.6 (M-1)
[Spectrum 0013](Ref. 0022)

TLC, chloroform-methanol-acetic acid-water (65:4:31.5:3.5) Rf 0.44 (Ref. 0022)TLC, chloroform-methanol-conc. ammonia (65:35:5) Rf 0.26(Ref. 0019)
Halobacterium salinarium (Ref. 0022)/Natronobacterium sp. from India (Ref. 0030)




37
glucosyl mannosyl glucosyl archaeol (Ref. 0024/0070/0093/0114/0093)
1-[D-glucopyranosyl (b1'-6')-D-mannopyranosyl (a1'-2')a-D-glucopyranosyl]-2,3-di-O-(3'',7'',11'',15''-tetramethyl)hexadecyl-sn-glycerol(Ref. 0024/0070/0093/0114/0093)
EEL0037
Yosuke Koga
Glcp(b1-6)-Manp(a1-2)-aGlcp-ArOH/TGA-2 (Ref. 0024)
C61H118O18 1139.579

[a]D = +34.6 degree; MD = +394 degree (Ref. 0024)



chromatogram,
[Chromatogram 0010] (Ref. 0024)
HALOBACTERIUM CUTIRUBRUM (Ref. 0093)/Halobacterium marismortui (Haloarcula) (Ref. 0024)




38
2-HSO3-mannosyl glucosyl archaeol(Ref. 0025)
1-[2'-hydroxysulfonyloxy-D-mannopyranosyl (a1'-2')a-D-glucopyranosyl]-2,3-di-O-(3'',7'',11'',15''-tetramethyl)hexadecyl-sn-glycerol
EEL0038
Yosuke Koga
2-HSO3-Manp(a1-2)-aGlcp-ArOH/S-DGA-5 (Ref. 0025)
C55H108O16S 1057.502

13C-NMR, 68.92 (C1 of Gro), 78.52 (C2 of Gro), 72.27 (C3 of Gro), 70.11 (C1 of sn-3 alkyl), 68.92 (C1 of sn-2 alkyl), 97.69 (C1 of Glc), 78.18 (C2 of Glc), 73.52 (C3 of Glc), 71.45 (C4 of Glc), 74.11 (C5 of Glc), 61.65 (C6 of Glc), 97.69 (C1 of Man), 77.94 (C2 of Man), 71.88 (C3 of Man), 68.66 (C4 of Man), 74.84 (C5 of Man), 62.56 (C6 of Man)


TLC, chloroform-methanol-water (65:25:4) Rf 0.26TLC, chloroform-methanol-acetic acid-water (85:22.5:10:4) Rf 0.30
Halobacterium trapanicum(Ref. 0025)




39
6-HSO3-mannosyl glucosyl archaeol(Ref. 0026/0070/0093/0095/0098)
1-[6'-hydroxysulfonyloxy-D-mannopyranosyl (a1'-2')-a-D-glucopyranosyl] 2,3-di-O-(3'',7'',11'',15''-tetramethyl)hexadecyl-sn-glycerol
EEL0039
Yosuke Koga
6-HSO3-Manp(a1-2)-aGlcp-ArOH/S-DGA-1/S-DGD-1 (Ref. 0026)
C55H108O16S 1057.502

[a]D = +42.8degree; MD = +466.7 degree (Ref. 0026)

[Spectrum 0015](Ref. 0029)O-H, 3420cm-1; CH3 & CH2, 2970, 2940, 2880, 1470cm-1; isopropyl, 1385, 1370cm-1; S=O, 1250cm-1; ether C-O-C, 1100cm-1; alcoholic C-O, 1070cm-1 (Ref. 0026)


chromatogram,
[Chromatogram 0011](Ref. 0026)
Haloferax mediterranei (Ref. 0029)/halophilic bacterial strain (R-4) (Haloferax) (Ref. 0026)/Halococcus(Ref. 0036)




40
mannosyl glucosyl archaeol(Ref. 0026)
1-[D-mannopyranosyl (a1-2)-a-D-glucopyranosyl] 2,3-di-O-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol(Ref. 0070/0093/0098)
EEL0040
Yosuke Koga
Manp(a1-2)-aGlcp-ArOH/DGA-1(Ref. 0026)
C55H108O13 977.438

[a]D = +61.1 degree; MD = +597 degree (Ref. 0026)



chromatogram,
[Chromatogram 0011](Ref. 0026)
Haloferax(Ref. 0026)/Halobacterium cutirubrum(Ref. 0070/0093/0098)




41
2-HSO3-mannosyl glucosyl archaeol(Ref. 0027)
1-[2'-hydroxysulfonyloxy-D-mannopyranosyl (a1'-4')a-D-glucopyranosyl] 2,3-di-O-(3'',7'',11'',15''-tetramethyl)hexadecyl-sn-glycerol
EEL0041
Yosuke Koga
2-HSO3-Manp(a1-4)-a-Glcp-ArOH/S-DGA-3 (Ref. 0027)
C55H108O16S 1057.502

[a]D = +26.4 degree (Ref. 0027)
S=O, 1250cm-1; S-O-C, 830cm-1(Ref. 0027)
1H-NMR, 4.78, 4.7313C-NMR, 71.5 (C1 of Gro), 78.4 (C2 of Gro), 72.27 (C3 of Gro), 70.7 (C1 of sn-3 alkyl), 68.5 (C1 of sn-2 alkyl), 96.9 (C1 of Glc), 72.0 (C2 of Glc), 72.2 (C3 of Glc), 77.1 (C4 of Glc), 70.5 (C5 of Glc), 61.5 (C6 of Glc), 96.9 (C1 of Man), 77.6 (C2 of Man), 71.8 (C3 of Man), 67.7 (C4 of Man), 73.4 (C5 of Man), 61.8 (C6 of Man)
positive FAB, m/z 1078 (M+Na); negative FAB, 1055 (M-H) (Ref. 0027)

TLC, chloroform-methanol-water (65:25:4) Rf 0.35 (Ref. 0027)
Halobacterium (Halorubrum) sodomense (Ref. 0027)/(Ref. 0028)




42
2,6-di-HSO3-mannosyl glucosyl archaeol (Ref. 0029)
1-[2',6'-hydroxysulfonyloxy-D-mannopyranosyl (a1'-2')-a-D-glucopyranosyl] 2,3-di-O-(3'',7'',11'',15''-tetramethyl)hexadecyl-sn-glycerol
EEL0042
Yosuke Koga
2,6-diHSO3-Manp(a1-2)-a-Glcp-ArOH/S2-DGA-1 (Ref. 0029)
C55H108O19S2 1137.567

1H-NMR
[Spectrum 0019](Ref. 0029)13C-NMR
[Spectrum 0020](Ref. 0029)13C-NMR, 95.74 (C1 of Glc), 74.78 (C2 of Glc), 71.44 (C3 of Glc), 70.14 (C4 of Glc), 72.54 (C5 of Glc), 60.84 (C6 of Glc), 95.66 (C1 of Man), 75.41 (C2 of Man), 69.42 (C3 of Man), 67.76 (C4 of Man), 71.44 (C5 of Man), 66.08 (C6 of Man) (Ref. 0029)

[Spectrum 0018] (Ref. 0029)negative FAB, m/z 1157 (M+Na-2H), 1055 (M-SO3H) (Ref. 0029)

chromatogram,
[Chromatogram 0012](Ref. 0029)TLC, chloroform-methanol-acetic acid-water (85:22.5:10:4, double development) Rf 0.18
Natrialba(Ref. 0029)




43
2,6-di-HSO3-mannosyl glucosyl C20,C25-archaeol(Ref. 0029)
1-[2',6'-hydroxysulfonyloxy-D-mannopyranosyl (a1'-2')-a-D-glucopyranosyl] 2-O-(3'',7'',11'',15''-tetramethyl)hexadecyl-3-O-(3''',7''',11''',15''',19'''-pentamethyl)icosanyl-sn-glycerol
EEL0043
Yosuke Koga
2,6-diHSO3-Manp(a1-2)-a-Glcp-C20,C25-ArOH/S2-DGA-1 (Ref. 0029)
C60H118O19S2 1207.700

1H-NMR
[Spectrum 0019](Ref. 0029)13C-NMR
[Spectrum 0020] (Ref. 0029)13C-NMR, 95.74 (C1 of Glc), 74.78 (C2 of Glc), 71.44 (C3 of Glc), 70.14 (C4 of Glc), 72.54 (C5 of Glc), 60.84 (C6 of Glc), 95.66 (C1 of Man), 75.41 (C2 of Man), 69.42 (C3 of Man), 67.76 (C4 of Man), 71.44 (C5 of Man), 66.08 (C6 of Man) (Ref. 0029)

[Spectrum 0018] (Ref. 0029)negative FAB, m/z 1227 (M+Na-2H), 1125 (M-SO3H) (Ref. 0029)

chromatogram,
[Chromatogram 0012](Ref. 0029)TLC, chloroform-methanol-acetic acid-water (85:22.5:10:4, double development) Rf 0.18
Natrialba(Ref. 0029)




44
C20,C25-archaetidylglycerol(Ref. 0029)
2-O-(3',7',11',15'-tetramethyl)hexadecyl-3-O-(3'',7'',11'',15'',19''-pentamethyl)icosanyl-sn-glycerol-1-phosphoglycerol
EEL0044
Yosuke Koga
C20,C25-AG(Ref. 0029)
C51H105O8P 877.348




chromatogram,
[Chromatogram 0012] (Ref. 0029)TLC, chloroform-methanol-acetic acid-water (85:22.5:10:4, double development) Rf 0.92
Natrialba(Ref. 0029)/Halococcus(Ref. 0036)




45
C20,C25-archaetidyl glycero(methyl)phosphate(Ref. 0029)
2-O-(3',7',11',15'-tetramethyl)hexadecyl-3-O-(3'',7'',11'',15'',19''-pentamethyl)icosanyl-sn-glycerol-1-phosphoglycerol-(methyl)phosphate
EEL0045
Yosuke Koga
C20,C25-AGP-Me(Ref. 0029)
C52H108O11P2 971.355




chromatogram,
[Chromatogram 0012] (Ref. 0029)TLC, chloroform-methanol-acetic acid-water (85:22.5:10:4, double development) Rf 0.68
Natrialba(Ref. 0029)




46
glucosyl glucosyl archaeol(Ref. 0030)
1-[D-glucopyranosyl-(b1-6)-a-D-glucopyranosyl]-2,3-di-O-(3'',7'',11'',15''-tetramethyl)hexadecyl-sn-glycerol
EEL0046
Yosuke Koga
Glcp(b1-6)-a-Glcp-C20,C20-ArOH/DGA-4 (Ref. 0030)
C55H108O13 977.438

1H-NMR, 4.125-4.150 (doublet, J, 7.5Hz); 4.613-4.625 (doublet, J, 3.75 Hz)
negative FAB, m/z 976 (M-H);

TLC, chloroform-methanol-conc.ammonia (65:35:5) Rf 0.20TLC, chloroform-methanol-acetic acid-water (85:22.5:8:3, ) Rf 0.39
Natronobacterium sp. from India(Ref. 0030)




47
glucosyl-glucosyl-tetraunsat.-C20,C20-archaeol(Ref. 0030)
EEL0047
Yosuke Koga
Glcp(b1-6)-a-Glcp-tetraunsat.-C20,C20-ArOH/DGA-4 (Ref. 0030)
C60H118O13 1047.571

1H-NMR, 4.125-4.150 (doublet, J, 7.5Hz); 4.613-4.625 (doublet, J, 3.75 Hz)
negative FAB, m/z 967.8 (M-H);


Natronobacterium sp. from India(Ref. 0030)




48
glucosyl-glucosyl-tetraunsat.-C20,C25-archaeol(Ref. 0030)
EEL0048
Yosuke Koga
Glcp(b1-6)-a-Glcp-tetraunsat.-C20,C25-ArOH/DGA-4 (Ref. 0030)
C65H128O13 1117.704

1H-NMR, 4.125-4.150 (doublet, J, 7.5Hz); 4.613-4.625 (doublet, J, 3.75 Hz)
negative FAB, m/z 1037.6 (M-H);

TLC, chloroform-methanol-conc.ammonia (65:35:5) Rf 0.20TLC, chloroform-methanol-acetic acid-water (85:22.5:8:3, ) Rf 0.44
Natronobacterium sp. from India(Ref. 0030)




49
glucosyl-glucosyl-monounsat.-C20,C20- hydroxyarchaeol(Ref. 0030)
EEL0049
Yosuke Koga
Glcp(b1-6)-a-Glcp-OH-C20, monounsat.-C20-ArOH/DGA-4 (Ref. 0030)
C60H118O14 1063.571

1H-NMR, 4.125-4.150 (doublet, J, 7.5Hz); 4.613-4.625 (doublet, J, 3.75 Hz)
negative FAB, m/z 989.7 (M-H);


Natronobacterium sp. from India(Ref. 0030)




50
glucosyl-glucosyl-diunsat. C20,C25- hydroxyarchaeol(Ref. 0030)
EEL0050
Yosuke Koga
Glcp(b1-6)-a-Glcp-OH-C20, diunsat.-C25-ArOH/DGA-4 (Ref. 0030)

1H-NMR, 4.125-4.150 (doublet, J, 7.5Hz); 4.613-4.625 (doublet, J, 3.75 Hz)
negative FAB, m/z 1057 (M-H);


Natronobacterium sp. from India(Ref. 0030)




51
glucosyl-glucosyl-diunsat. C25,C25-hydroxyarchaeol(Ref. 0030)
EEL0051
Yosuke Koga
Glcp(b1-6)-a-Glcp-OH-C25, diunsat. C25-ArOH/DGA-4 (Ref. 0030)

1H-NMR, 4.125-4.150 (doublet, J, 7.5Hz); 4.613-4.625 (doublet, J, 3.75 Hz)
negative FAB, m/z 1127 (M-H);


Natronobacterium sp. from India(Ref. 0030)




52
archaetidylglycero cyclic phosphate(Ref. 0031)
2,3-di-O-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol-1-phosphoglycerol-1'',2''-cyclic phosphate
EEL0052
Yosuke Koga
AGcycP(Ref. 0031)/PL2
C46H94O10P2 869.180

13C-NMR, 65.5 (C1 of Gro), 78.1 (C2 of Gro), 71.5 (C3 of Gro), 66.8 (C1' of Gro), 74.6 (C2' of Gro), 66.9 (C3' of Gro), 69.5 (C1 of sn-2 alkyl), 70.8 (C1 of sn-3 alkyl)


chromatogram,
[Chromatogram 0013](Ref. 0031)TLC, chloroform-methanol-water (65:25:4) Rf 0.3 (Ref. 0031)
Natronococcus occultus(Ref. 0031)




53
C20,C25-archaetidyl glycero cyclic phosphate(Ref. 0031)
2-O-(3',7',11',15'-tetramethyl)hexadecyl-3'- O-(3'',7'',11'',15'',19''-pentamethyl)icosanyl- sn-glycerol-1-phosphoglycerol-1''',2'''-cyclic phosphate
EEL0053
Yosuke Koga
C20,C25-AGcycP(Ref. 0031)
C51H104O10P2 939.313

13C-NMR, 65.5 (C1 of Gro), 78.1 (C2 of Gro), 71.5 (C3 of Gro), 66.8 (C1' of Gro), 74.6 (C2' of Gro), 66.9 (C3' of Gro), 69.5 (C1 of sn-2 alkyl), 70.8 (C1 of sn-3 alkyl)


chromatogram,
[Chromatogram 0013](Ref. 0031)TLC, chloroform-methanol-water (65:25:4) Rf 0.3 (Ref. 0031)
Natronococcus occultus(Ref. 0031)




54
dihexadecylglycerol(Ref. 0032)/dipalmitylglycerol
1,2-di-O-hexadecyl-sn-glycerol
EEL0054
Yosuke Koga
diC16-Gro(Ref. 0032)
C35H72O3 540.944

[a]D = -3.1 degree; MD = -16.7 degree (Ref. 0032)

GC-methane-CI-MS, 541 (M+1)

chromatogram,
[Chromatogram 0014] (component 2),
[Chromatogram 0015] (Ref. 0032)TLC, n-hexane-diethyl ether-acetic acid (70:30:1) Rf 0.42 (Ref. 0032)
Thermodesulfotobacterium commune(Ref. 0032)/Aquifex pyrophilus(Ref. 0034)




55
1-hexadecyl-2-heptadecyl-glycerol(Ref. 0032)
1-O-hexadecyl-2-O-heptadecyl-sn-glycerol
EEL0055
Yosuke Koga
C16, C17-Gro(Ref. 0032)
C36H74O3 554.971

[a]D = -3.1 degree; MD = -16.7 degree (Ref. 0032)

GC-methane-CI-MS, 555 (M+1)

chromatogram,
[Chromatogram 0014](component 2),
[Chromatogram 0015] (Ref. 0032)TLC, n-hexane-diethyl ether-acetic acid (70:30:1) Rf 0.42 (Ref. 0032)
Thermodesulfotobacterium commune(Ref. 0032)




56
diheptadecyl-glycerol(Ref. 0032)
1,2-di-O-heptadecyl-sn-glycerol
EEL0056
Yosuke Koga
di-C17-Gro(Ref. 0032)
C37H76O3 568.998

[a]D = -3.1 degree; MD = -16.7 degree (Ref. 0032)

GC-methane-CI-MS, 569 (M+1)
[Spectrum 0022]

chromatogram,
[Chromatogram 0014] (component 2),
[Chromatogram 0015] (Ref. 0032)TLC, n-hexane-diethyl ether-acetic acid (70:30:1) Rf 0.42 (Ref. 0032)
Thermodesulfotobacterium commune(Ref. 0032)




57
heptadecyl octadecyl glycerol(Ref. 0032)
1-O-heptadecyl-2-O- octadecyl-sn-glycerol
EEL0057
Yosuke Koga
C17,C18-Gro(Ref. 0032)
C38H78O3 583.024

[a]D = -3.1 degree; MD = -16.7 degree (Ref. 0032)

GC-methane-CI-MS, 583 (M+1)

chromatogram,
[Chromatogram 0014](component 2),
[Chromatogram 0015](Ref. 0032)TLC, n-hexane-diethyl ether-acetic acid (70:30:1) Rf 0.42 (Ref. 0032)
Thermodesulfotobacterium commune(Ref. 0032)/Aquifex pyrophilus(Ref. 0034)




58
dioctadecyl-glycerol(Ref. 0032)
1,2-di-O-octadecyl-sn-glycerol
EEL0058
Yosuke Koga
di-C18-Gro(Ref. 0032)
C39H80O3 597.051

[a]D = -3.1 degree; MD = -16.7 degree (Ref. 0032)

GC-methane-CI-MS, 597 (M+1)

chromatogram,
[Chromatogram 0014](component 2),
[Chromatogram 0015] (Ref. 0032)TLC, n-hexane-diethyl ether-acetic acid (70:30:1) Rf 0.42 (Ref. 0032)
Thermodesulfotobacterium commune(Ref. 0032)




59
isohexadecyl-glycerol(Ref. 0032)
1-O-(14'-methyl)pentadecyl-sn-glycerol(Ref. 0032)
EEL0059
Yosuke Koga
isoC16-Gro(Ref. 0032)
C19H40O3 316.519


GC-ammonia-CI-MS, 418 (M+18)

chromatogram,
[Chromatogram 0014] (component 3),
[Chromatogram 0016]TLC, n-hexane-diethyl ether-acetic acid (70:30:1) Rf 0.06 (Ref. 0032)
Thermodesulfotobacterium commune(Ref. 0032)




60
hexadecyl-glycerol(Ref. 0032)
1-O-hexadecyl-sn-glycerol
EEL0060
Yosuke Koga
C16-Gro(Ref. 0032)
C19H40O3 316.519


GC-ammonia-CI-MS, 418 (M+18)

chromatogram,
[Chromatogram 0014] (component 3),
[Chromatogram 0016]TLC, n-hexane-diethyl ether-acetic acid (70:30:1) Rf 0.06 (Ref. 0032)
Thermodesulfotobacterium commune(Ref. 0032)




61
isoheptadecyl-glycerol(Ref. 0032)
1-O-(15'-methyl)hexadecyl-sn-glycerol
EEL0061
Yosuke Koga
isoC17-Gro(Ref. 0032)
C20H42O3 330.546


GC-ammonia-CI-MS, 432 (M+18)

chromatogram,
[Chromatogram 0014] (component 3),
[Chromatogram 0016]TLC, n-hexane-diethyl ether-acetic acid (70:30:1) Rf 0.06 (Ref. 0032)
Thermodesulfotobacterium commune(Ref. 0032)




62
anteisoheptadecyl-glycerol(Ref. 0032)
1-O-(14'-methyl)hexadecyl-sn-glycerol
EEL0062
Yosuke Koga
anteisoC17-Gro(Ref. 0032)
C20H42O3 330.546


GC-ammonia-CI-MS, 432 (M+18)
[Spectrum 0023]

chromatogram,
[Chromatogram 0014] (component 3),
[Chromatogram 0016]TLC, n-hexane-diethyl ether-acetic acid (70:30:1) Rf 0.06 (Ref. 0032)
Thermodesulfotobacterium commune(Ref. 0032)




63
isooctadecyl-glycerol(Ref. 0032)
1-O-(16-methyl)heptaptadecyl-sn-glycerol
EEL0063
Yosuke Koga
isoC18-Gro(Ref. 0032)
C21H44O3 344.572


GC-ammonia-CI-MS, 446 (M+18)

chromatogram,
[Chromatogram 0014] (component 3),
[Chromatogram 0016]TLC, n-hexane-diethyl ether-acetic acid (70:30:1) Rf 0.06 (Ref. 0032)
Thermodesulfotobacterium commune(Ref. 0032)




64
octadecyl-glycerol(Ref. 0032)
1-O-octadecyl-sn-glycerol
EEL0064
Yosuke Koga
C18-Gro(Ref. 0032)
C21H44O3 344.572


GC-ammonia-CI-MS, 446 (M+18)

chromatogram,
[Chromatogram 0014] (component 3),
[Chromatogram 0016]TLC, n-hexane-diethyl ether-acetic acid (70:30:1) Rf 0.06 (Ref. 0032)
Thermodesulfotobacterium commune(Ref. 0032)




65
isononadecyl-glycerol(Ref. 0032)
1-O-(17'-methyl)octadecyl-sn-glycerol
EEL0065
Yosuke Koga
isoC19-Gro(Ref. 0032)
C22H46O3 358.599


GC-ammonia-CI-MS, 460 (M+18)

chromatogram,
[Chromatogram 0014] (component 3),
[Chromatogram 0016]TLC, n-hexane-diethyl ether-acetic acid (70:30:1) Rf 0.06 (Ref. 0032)
Thermodesulfotobacterium commune(Ref. 0032)




66
anteisononadecyl-glycerol(Ref. 0032)
1-O-(16'-methyl)octadecyl-sn-glycerol
EEL0066
Yosuke Koga
anteisoC19-sn-Gro(Ref. 0032)
C22H46O3 358.599


GC-ammonia-CI-MS, 460 (M+18)

chromatogram,
[Chromatogram 0014] (component 3),
[Chromatogram 0016]TLC, n-hexane-diethyl ether-acetic acid (70:30:1) Rf 0.06 (Ref. 0032)
Thermodesulfotobacterium commune(Ref. 0032)




67
diabolic acid-containing lipid 22/di(butyroyl PlaG) diabolate(Ref. 0033)
EEL0067
Yosuke Koga
di(acyl PlaG) diabolate(Ref. 0033)
C84H160O20P2 1552.105





Butyrivibrio sp.(Ref. 0033)




68
diabolic acid containing alkenyl galactophospholipid 14/(Ref. 0033)
EEL0068
Yosuke Koga
C87H164O20P 1561.195





Butyrivibrio sp.(Ref. 0033)




69
diheptadecyl-glycerol(Ref. 0034)
1,2-di-O-heptadecyl-sn-glycerol
EEL0069
Yosuke Koga
di-C17-Gro(Ref. 0034)
C37H76O3 568.998





Aquifex pyrophilus(Ref. 0034)




70
19:cyc acyl plasmenylglycerol(Ref. 0038)
EEL0070
Yosuke Koga
19:cyc acyl PlaG(Ref. 0038)





Clostridium butyricum(Ref. 0038)




71
C20,C25-archaetidylglycerophosphate(Ref. 0036)
2-(3'',7'',11''.15'',19''-pentamethyl)icosyl-3-(3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol-1-phosphoglycerophosphate
EEL0071
Yosuke Koga
C20,C25-AGP(Ref. 0036)
C51H106O11P2 957.328

1H-NMR, 0.82 (CH3); 1.0-1.1 ((CH3)2C-); 1.2-1.3 (CH2); 1.48-1.50 (CH-); 3.42-3.44 (RCH2-O-); 3.56-3.58 (-CH2-O-R, -CH-O-R); 3.9-4.0 (-CH2-O-P)
negative FAB, m/z 972 (M-NH4)

TLC, chloroform-methanol-acetic acid-water (85:22.5:10:4) double development Rf 0.44 chloroform-methanol-acetic acid (65:4:35) Rf 0.54 chloroform-methanol-ammonia (65:35:5) double development Rf 0.27 (Ref. 0036)
Halococcus(Ref. 0036)/Clostridium acetobutylicum(Ref. 0148)




72 No image
phospho-(galactosyl, mannosyl, glucosyl)-monounsaturated ArOH(Ref. 0036)
EEL0072
Yosuke Koga
H2PO3-Gal-Man-Glc-ArOH/P-TGD(Ref. 0036)

1H-NMR, 0.82 (CH3); 1.60-1.65 (allylic CH3); 2.0 (allylic CH2); 5.1-5.2 (olefinic isoprenoid H)


TLC, chloroform-methanol-acetic acid-water (85:22.5:10:4) double development Rf 0.14 chloroform-methanol-acetic acid (65:4:35) Rf 0.04 chloroform-methanol-ammonia (65:35:5) double development Rf 0.11(Ref. 0036)
Halococcus(Ref. 0036)




73
C20,unsat.C20-archaetidylglycerophosphate(Ref. 0036)
EEL0073
Yosuke Koga
C20,unsat.C20-AGP(Ref. 0036)




TLC, chloroform-methanol-acetic acid-water (85:22.5:10:4) double development Rf 0.39chloroform-methanol-acetic acid (65:4:35) Rf 0.50chloroform-methanol-ammonia (65:35:5) double development Rf 0.23(Ref. 0036)
Halococcus(Ref. 0036)




74
plasmenylserine(Ref. 0035)
EEL0074
Yosuke Koga
PlaS(Ref. 0035)




chromatogram,
[Chromatogram 0017]
Megasphaera elsdenii(Ref. 0035)




75
16:0 acyl plasmenylmethylethanolamine(Ref. 0038)
EEL0075
Yosuke Koga
16:0 acyl PlaME(Ref. 0038)





Clostridium butyricum(Ref. 0038)




76
16:1 acyl plasmenylmethylethanolamine(Ref. 0038)
EEL0076
Yosuke Koga
16:1 acyl PlaME(Ref. 0038)





Clostridium butyricum(Ref. 0038)




77
17:cyc acyl plasmenylmethylethanolamine(Ref. 0038)
EEL0077
Yosuke Koga
17:cyc acyl PlaME(Ref. 0038)





Clostridium butyricum(Ref. 0038)




78
18:0 acyl plasmenylmethylethanolamine(Ref. 0038)
EEL0078
Yosuke Koga
18:0 acyl PlaME(Ref. 0038)





Clostridium butyricum(Ref. 0038)




79
18:1 acyl plasmenylmethylethanolamine(Ref. 0038)
EEL0079
Yosuke Koga
18:1 acyl PlaME(Ref. 0038)





Clostridium butyricum(Ref. 0038)




80
19:cyc acyl plasmenylmethylethanolamine(Ref. 0038)
EEL0080
Yosuke Koga
19:cyc acyl PlaME(Ref. 0038)





Clostridium butyricum(Ref. 0038)




81
16:0 acyl plasmenylethanolamine(Ref. 0038)
EEL0081
Yosuke Koga
16:0 acyl PlaE(Ref. 0038)





Clostridium butyricum(Ref. 0038)




82
16:1 acyl plasmenylethanolamine(Ref. 0038)
EEL0082
Yosuke Koga
16:1 acyl PlaE(Ref. 0038)





Clostridium butyricum(Ref. 0038)




83
17:cyc acyl plasmenylethanolamine(Ref. 0038)
EEL0083
Yosuke Koga
17:cyc acyl PlaE(Ref. 0038)





Clostridium butyricum(Ref. 0038)




84
18:0 acyl plasmenylethanolamine(Ref. 0038)
EEL0084
Yosuke Koga
18:0 acyl PlaE(Ref. 0038)





Clostridium butyricum(Ref. 0038)




85
18:1 acyl plasmenylethanolamine(Ref. 0038)
EEL0085
Yosuke Koga
18:1 acyl PlaE(Ref. 0038)





Clostridium butyricum(Ref. 0038)




86
19:cyc acyl plasmenylethanolamine(Ref. 0038)
EEL0086
Yosuke Koga
19:cyc acyl PlaE(Ref. 0038)





Clostridium butyricum(Ref. 0038)




87
16:0 acyl plasmenylglycerol(Ref. 0038)
EEL0087
Yosuke Koga
16:0 acyl PlaG(Ref. 0038)





Clostridium butyricum(Ref. 0038)/Clostridium acetobutylicum(Ref. 0148)




88
16:1 acyl plasmenylglycerol(Ref. 0038)
EEL0088
Yosuke Koga
16:1 acyl PlaG(Ref. 0038)





Clostridium butyricum(Ref. 0038)/Clostridium acetobutylicum(Ref. 0148)




89
17:cyc acyl plasmenylglycerol(Ref. 0038)
EEL0089
Yosuke Koga
17:cyc acyl PlaG(Ref. 0038)





Clostridium butyricum(Ref. 0038)/Clostridium acetobutylicum(Ref. 0148)




90
18:0 acyl plasmenylglycerol(Ref. 0038)
EEL0090
Yosuke Koga
18:0 acyl PlaG(Ref. 0038)





Clostridium butyricum(Ref. 0038)/Clostridium acetobutylicum(Ref. 0148)




91
18:1 acyl plasmenylglycerol(Ref. 0038)
EEL0091
Yosuke Koga
18:1 acyl PlaG(Ref. 0038)





Clostridium butyricum(Ref. 0038)/Clostridium acetobutylicum(Ref. 0148)




92
diabolic acid-containing lipid 26/di-PlaG diabolate(Ref. 0033)
EEL0092
Yosuke Koga
di-PlaG diabolate(Ref. 0033)
C76H148O18P2 1411.925





Butyrivibrio sp.(Ref. 0033)




93
diabolic acid-containing lipid 20/butyroyl PlaG, palmitoyl PlaG diabolate(Ref. 0033)
EEL0093
Yosuke Koga
di(acylPlaG) diabolate(Ref. 0033)
C96H184O20P2 1720.424





Butyrivibrio sp.(Ref. 0033)




94
diabolic acid containing alkenyl galactophospholipid 11/(Ref. 0033)
EEL0094
Yosuke Koga
C87H164O20P 1561.195





Butyrivibrio sp.(Ref. 0033)




95
diabolic acid-containing lipid 25/butyroyl PlaG,PlaG diabolate(Ref. 0033)
EEL0095
Yosuke Koga
acyl PlaG,PlaG diabolate(Ref. 0033)
C80H154O19P2 1482.015





Butyrivibrio sp.(Ref. 0033)




96 No image
phospho-galactosyl-mannosyl-glucosyl-ArOH(Ref. 0036)
EEL0096
Yosuke Koga
H2PO3-Gal-Man-Glc-ArOH/P-TGD(Ref. 0036)




TLC, chloroform-methanol-acetic acid-water (85:22.5:10:4) double development Rf 0.14 chloroform-methanol-acetic acid (65:4:35) Rf 0.04 chloroform-methanol-ammonia (65:35:5) double development Rf 0.11(Ref. 0036)
Halococcus(Ref. 0036)




97
a-hydroxyarchaeol
2-O-(3',7',11',15'-tetramethyl)hexadecyl-3-O-(3'-hydroxy-3',7',11',15'-tetramethyl)hexadecyl-sn-glycerol/ 2-O-(3'-hydroxy)phytanyl-3-O-phytanyl-sn-glycerol(Ref. 0015)
EEL0097
Yosuke Koga
a-OH-ArOH
C43H88O4 669.156

13C-NMR, 68.77 (sn-2 C1), 68.90 (sn-3 C1), 37.10 (sn-2 C2), 39.78 (sn-3 C2), 29.90 (sn-2 C3), 72.37 (sn-3 C3), 37.32-37.57 (sn-2 C4), 42.92 (sn-2 C4), 24.39 (sn-2 C5), 21.51 (sn-3 C5), 37.32-37.57 (sn-2 C6), 37.71 (sn-3 C6) (Ref. 0015)
[Spectrum 0024]
[Spectrum 0025]
[Spectrum 0026] (Ref. 0015)



Methanosaeta concilii (Ref. 0015), Methanosphaera stadtmanae (Ref. 0121), Methanococcus thermolithotrophicus (Ref. 0121)




98
3-palmitylglycerophosphate
3-O-hexadecyl-sn-glycerol-1-phosphate(Ref. 0048)
EEL0098
Yosuke Koga
C16:0-GP monoether/3Hx-GPA
C19H41O6P 396.499
prepared by alkaline hydrolysis of 3-O-hexadecyl-2-acetyl GPC followed by hydrolysis with phospholipase D (Ref. 0048)





prepared by alkaline hydrolysis of 3-O-hexadecyl-2-acetyl GPC followed by hydrolysis with phospholipase D (Ref. 0048)



99
3-O-hexadecyl-sn-glycero-1-phosphocholine(Ref. 0048)
EEL0099
Yosuke Koga
C16:0-GPC/3Hx-GPC
C24H52O6PN 481.647





synthetic compound




100
1-O-hexadecylglycerol (Ref. 0040)
EEL0100
Yosuke Koga
16:0-Gro monoether
C19H40O3 316.519

58.5degC(Ref. 0067)



TLC, THF-H2O (1:1) Rf 0.44
synthetic product




101
1-O-octadecylglycerol (Ref. 0040)
EEL0101
Yosuke Koga
18:0-Gro monoether
C19H40O3 316.519

58.5degC(Ref. 0067)



TLC, THF-H2O (1:1) Rf 0.34
synthetic product




102
1-O-cis-9-hexadecenyglycerol (Ref. 0040)
EEL0102
Yosuke Koga
16:1-Gro monoether
C19H38O3 314.503

58.5degC(Ref. 0067)



TLC, THF-H2O (1:1) Rf 0.51
synthetic product




103
1-O-cis-9-octadecenyglycerol (Ref. 0040)
EEL0103
Yosuke Koga
18:1-Gro monoether
C21H42O3 342.556

58.5degC(Ref. 0067)



TLC, THF-H2O (1:1) Rf 0.40
synthetic product




104
1-O-trans-9-octadecenyglycerol (Ref. 0040)
EEL0104
Yosuke Koga
18:1-Gro monoether
C21H42O3 342.556

58.5degC(Ref. 0067)



TLC, THF-H2O (1:1) Rf 0.42
synthetic product




105
1-palmityl-2-acetylglycerophosphate
1-O-hexadecyl-2-acetyl-sn-glycerol-3-phosphate(Ref. 0048)
EEL0105
Yosuke Koga
C16:0-Ac-GP monoether/1Hx-2Ac-GPA
C19H41O6P 396.499
prepared by acetylation of 1-O-hexadecyl-GPC with acetic anhydride followed by hydrolysis with phospholipase D (Ref. 0048)




synthetic compound
prepared by acetylation of 1-O-hexadecyl-GPC with acetic anhydride followed by hydrolysis with phospholipase D (Ref. 0048)



106
3-palmityl-2-acetylglycerophosphate
3-O-hexadecyl-2-acetyl-sn-glycerol-1-phosphate(Ref. 0048)
EEL0106
Yosuke Koga
C16:0-Ac-GP monoether/3Hx-2Ac-GPA
C19H41O6P 396.499
prepared by acetylation of 1-O-hexadecyl-GPC with acetic anhydride followed by hydrolysis with phospholipase D (Ref. 0048)




synthetic compound
prepared by acetylation of 1-O-hexadecyl-GPC with acetic anhydride followed by hydrolysis with phospholipase D (Ref. 0048)



107
1-palmityl-2-acetylglycerophosphocholine
3-O-hexadecyl-2-acetyl-sn-glycero-1-phosphocholine(Ref. 0048)
EEL0107
Yosuke Koga
C16:0-Ac-GPC monoether/3Hx-2Ac-GPC
C19H41O6P 396.499
prepared by acetylation of 1-O-HEXADECYL-GPC with acetic anhydride(Ref. 0048)




synthetic compound
prepared by acetylation of 1-O-HEXADECYL-GPC with acetic anhydride(Ref. 0048)



108
PAF
1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine(Ref. 0048)
EEL0108
Yosuke Koga
C16:0-Ac-GPC/1Hx-2Ac-GPC
C24H52O6PN 481.647










109
1-(9'-cis-octadecenyl)-2-octadecanoylglycerol/1-oleyl-2-stearoylglycerol
1-O-(9'-cis-octadecenyl)-2-O-octadecanoylglycerol(Ref. 0049)
EEL0109
Yosuke Koga
C39H76O4 609.018

[a]D = -3.9degMD = -23.8deg




synthetic compound




110
1-(9'-cis-octadecenyl)-3-octadecanoylglycerol/1-oleyl-3-stearoylglycerol
1-O-(9'-cis-octadecenyl)-3-O-octadecanoylglycerol(Ref. 0049)
EEL0110
Yosuke Koga
C39H76O4 609.018

43.0-43.5degC
[a]D = -0.7deg/MD = -4.3deg




synthetic compound




111
1-(9'-cis-octadecenyl)-2,3-di-hexadecanoylglycerol/1-oleyl-2,3-palmitoylglycerol
1-O-(9'-cis-octadecenyl)-2,3-di-O-hextadecanoylglycerol(Ref. 0049)
EEL0111
Yosuke Koga
C53H102O5 819.374

36.5-37.5degC
[a]D = -6.6deg/MD = -55.3deg




synthetic compound




112
1-(9'-cis-octadecenyl)-2,3-di-octadecanoylglycerol/1-oleyl-2,3-stearoylglycerol
1-O-(9'-cis-octadecenyl)-2,3-di-O-octadecanoylglycerol(Ref. 0049)
EEL0112
Yosuke Koga
C57H110O5 875.480

37.0-38.0degC
[a]D = -6.5deg/MD = -56.4deg




synthetic compound




113
1,2-di-(9'-cis-octadecenyl)-3-tritylglycerol/1,2-oleyl-3-tritylglycerol
1,2-di-O-(9'-cis-octadecenyl)-3-O-tritylglycerol(Ref. 0049)
EEL0113
Yosuke Koga
C58H90O3 835.333

[a]D = +4.1deg/MD = +28.5deg




synthetic compound




114
1,2-di-(9'-cis-octadecenyl)-3-acetylglycerol/1,2-oleyl-3-acetylglycerol
1,2-di-O-(9'-cis-octadecenyl)-3-O-acetylglycerol(Ref. 0049)
EEL0114
Yosuke Koga
C41H78O4 635.056

[a]D = -5.2deg/MD = -33.0deg




synthetic compound




115
3-octadecylglycerol/3-stearylglycerol(Ref. 0049)
3-O-octadecylglycerol
EEL0115
Yosuke Koga
3-C18:0-Gro monoether
C21H44O3 344.572

70.5-71.5degC
[a]D = +16.0deg




synthetic product




116
3-hexadecylglycerol/3-palmitylglycerol(Ref. 0049)
3-O-hexadecylglycerol
EEL0116
Yosuke Koga
3-C16:0-Gro monoether
C19H40O3 316.519

65.5-66.5degC
[a]D = +17.5deg




synthetic product




117
1,2-ditosyl-3-octadecylglycerol/1,2-ditosyl-3-stearylglycerol
1,2-ditosyl-3-O-octadecylglycerol(Ref. 0049)
EEL0117
Yosuke Koga
1,2-diTs-3-C18:0-Gro monoether
C35H56O7S2 652.947 Download ChemDraw structure file

[a]D = +0.6deg




synthetic product




118
1,2-ditosyl-3-hexadecylglycerol/1,2-ditosyl-3-palmitylglycerol
1,2-ditosyl-3-O-hexadecylglycerol(Ref. 0049)
EEL0118
Yosuke Koga
1,2-diTs-3-C16:0-Gro monoether
C33H52O7S2 624.894

[a]D = +0.5deg




synthetic product




119
1-octadecyl-2,3-di-O-acetylglycerol/1-stearyl-2,3-di-O-acetylglycerol
1-O-octadecyl-2,3-di-O-acetylglycerol(Ref. 0049)
EEL0119
Yosuke Koga
C25H48O5 428.646

39.0-40.0degC
[a]D = -11.8deg




synthetic product




120
1-hexadecyl-2,3-di-O-acetylglycerol/1-palmityl-2,3-di-O-acetylglycerol
1-O-hexadecyl-2,3-di-O-acetylglycerol(Ref. 0049)
EEL0120
Yosuke Koga
C23H44O5 400.592

[a]D = -12.8deg




synthetic product




121
1-(9'-cis-octadecenyl)-2-octadecanoyl-3-glycerophosphoethanolamine/1-oleyl-2-stearoyl-3-glycerophosphoethanolamine
1-O-(9'-cis-octadecenyl)-2-O-octadecanoyl-3-glycerophosphoethanolamine(Ref. 0049)
EEL0121
Yosuke Koga
1-C18:1-2-C18:0-GPE monoether/ether analog of PE
C41H84O7NP 734.082

192-193deg
[a]D = +3.1deg/MD = 22.6deg




synthetic product




122
1-(9'-cis-octadecenyl)-2-octadecanoyl-3-glycerophosphocholine/1-oleyl-2-stearoyl-3-glycerophosphocholine
1-O-(9'-cis-octadecenyl)-2-O-octadecanoyl-3-glycerophosphocholine(Ref. 0049)
EEL0122
Yosuke Koga
1-C18:1-2-C18:0-GPC monoether/ether analog of PC
C44H89O7NP 775.154

232deg
[a]D = +2.6deg/MD = 20.6deg




synthetic product




123
3-O-{[2-(pyrrolidino)ethyl]-N-acetylcarbamoyl}-2-O-methyl-1-O-(octadecylcarbamoyl)glycerol(Ref. 0067)
EEL0123
Yosuke Koga
C32H61O6N3 583.843





synthetic product(Ref. 0067)




124
3-O-{[2-(N-morphoryl)ethyl]-N-acetylcarbamoyl}-2-O-methyl-1-O-(octadecylcarbamoyl)glycerol(Ref. 0067)
EEL0124
Yosuke Koga
C32H61O7N3 599.843





synthetic product(Ref. 0067)




125
plasmenylglycerol phosphatidic acid/plasmenylcardiolipin(Ref. 0148)/(Ref. 0152)
EEL0125
Yosuke Koga
PlaGPA/PlaCL(Ref. 0148)/(Ref. 0152)
Download ChemDraw structure file





Clostridium acetobutylicum(Ref. 0148)/Clostridium innocuum(Ref. 0152)




126
alkenyl form of monogalactosyl diradylglycerol(Ref. 0148)
1-O-alk-1'-enyl-2-O-acyl-3-O-galactosyl-sn-glycerol(Ref. 0148)
EEL0126
Yosuke Koga
Download ChemDraw structure file





Clostridium acetobutylicum(Ref. 0148)




127
alkenyl form of diglycosyl-diradylglycerol(Ref. 0148)
1-O-alk-1'-enyl-2-O-acyl-3-O-b-glucosylgalactosyl-sn-glycerol(Ref. 0148)
EEL0127
Yosuke Koga
Download ChemDraw structure file





Clostridium acetobutylicum(Ref. 0148)




128
phosphatidylglycerol acetal of plasmenylethanolamine(Ref. 0149)
EEL0128
Yosuke Koga
PGAPlaE(Ref. 0149)
C83H157O17P2N 1503.079 Download ChemDraw structure file

positive FAB-MS
[Spectrum 0035] (Ref. 0149), negative FAB-MS
[Spectrum 0036] (Ref. 0149),
[Spectrum 0037] (Ref. 0149)

Clostridium butyricum(Ref. 0149)




129
plasmenylglycerol acetal of plasmenylethanolamine(Ref. 0149)
EEL0129
Yosuke Koga
PlaGAPlaE(Ref. 0149)
C83H157O16P2N 1487.079 Download ChemDraw structure file


Clostridium butyricum(Ref. 0149)




130
phosphatidylglycerol acetal of plasmenylcardiolipin(Ref. 0150)
EEL0130
Yosuke Koga
PGAPlaCL(Ref. 0150)
Download ChemDraw structure file

1H-NMR, 3.53 ppm, 4.53 ppm, 5.9 ppm (a-vinyl ether proton), 5.1 ppm; 13C-NMR, 103 ppm, 65.3 ppm (Ref. 0150)


Clostridium innocuum(Ref. 0150)




131
plasmenylglycerol acetal of plasmenylcardiolipin(Ref. 0150)
EEL0131
Yosuke Koga
PlaGAPlaCL(Ref. 0150)
Download ChemDraw structure file

1H-NMR, 3.53 ppm, 4.53 ppm, 5.9 ppm (a-vinyl ether proton), 5.1 ppm; 13C-NMR, 103 ppm, 65.3 ppm (Ref. 0150)



Clostridium innocuum(Ref. 0150)




132
phosphatidylglycerol acetal of alkenylplasmenylcardiolipin(Ref. 0150)
EEL0132
Yosuke Koga
PGAPlaCL(Ref. 0150)
Download ChemDraw structure file

1H-NMR, 3.53 ppm, 4.53 ppm, 5.9 ppm (a-vinyl ether proton), 5.1 ppm; 13C-NMR, 103 ppm, 65.3 ppm (Ref. 0150)



Clostridium innocuum(Ref. 0150)




133 No image
lyso form of phosphatidylglycerol acetal of plasmenylcardiolipin(Ref. 0150)
EEL0133
Yosuke Koga
LPGAPlaCL(Ref. 0150)

1H-NMR, 3.53 ppm, 4.53 ppm, 3.6 ppm (Ref. 0150)



Clostridium innocuum(Ref. 0150)




134
phosphatidylglycerol acetal of plasmenylglycerol(Ref. 0150)
EEL0134
Yosuke Koga
PGAPlaG(Ref. 0150)
Download ChemDraw structure file





Clostridium innocuum(Ref. 0150)




135
3-O-{2'-[6''-(s-2'''-amino-1''',3'''-dihydroxypropane-3'''-phospho)-a-D-galactopyranosyl]-a-D-glucopyranosyl}-1-alk-1''''-enyl-2-O-acyl-sn-glycerol(Ref. 0151)
EEL0135
Yosuke Koga
Phosphoglycolipid I
Download ChemDraw structure file


[Spectrum 0044] (Ref. 0151),
[Spectrum 0045] (Ref. 0151),
[Spectrum 0046](Ref. 0151) 13C-NMR (in ppm), 98.27 (C1 of D-Gal), 69.43 (C2of D-Gal), 70.18 (C3 of D-Gal), 69.57 (C4of D-Gal), 70.70 (C5 of D-Gal), 65.31 (C6 of D-Gal), 59.47 (C1 of aminopropanediol), 53.98 (C2 of aminopropanediol), 63.41 (C3 of aminopropanediol), 97.28 (C1 of D-Glc), 78.11 (C2 of D-Glc), 72.61 (C3 of D-Glc), 70.18 (C4 of D-Glc), 72.81 (C5 of D-Glc), 61.57 (C6 of D-Glc), 63.34 (C1 of Gro), 70.61 (C2 of Gro), 66.49 (C3 of Gro) 1H-NMR (in ppm), 4.95 (H1 of D-Gal), 3.74 (H2 of D-Gal), 3.80 (H3 of D-Gal), 3.94 (H4 of D-Gal), 4.25 (H5 of D-Gal), 3.97 (H6 of D-Gal), 3.97 (H6' of D-Gal), 3.68 (H1 of aminopropanediol), 3.75 (H1' of aminopropanediol), 3.42 (H2 of aminopropanediol), 3.98 (H3 of aminopropanediol), 4.03 (H3' of aminopropanediol), 4.98 (H1 of D-Glc), 3.55 (H2 of D-Glc), 3.75 (H3 of D-Glc), 3.43 (H4 of D-Glc), 3.54 (H5 of D-Glc), 3.79 (H6 of D-Glc), 3.79 (H6' of D-Glc), 4.16 (H1 of Gro), 4.42 (H1' of Gro), 5.20 (H2 of Gro), 3.62 (H3 of Gro), 3.80 (H3' of Gro),

Clostridium innocuum(Ref. 0151)




136
3-O-{2'-[6''-(s-2'''-amino-1''',3'''-dihydroxypropane-3'''-phospho)-a-D-galactopyranosyl]-6'-O-acyl-a-D-glucopyranosyl}-1-alk-1''''-enyl-2-O-acyl-sn-glycerol(Ref. 0151)
EEL0136
Yosuke Koga
Phosphoglycolipid II
Download ChemDraw structure file



[Spectrum 0038] (Ref. 0151),
[Spectrum 0043] (Ref. 0151) 13C-NMR (in ppm), 98.77 (C1 of D-Gal), 69.27 (C2of D-Gal), 70.30 (C3 of D-Gal), 69.37 (C4of D-Gal), 70.58 (C5 of D-Gal), 64.89 (C6 of D-Gal), 59.39 (C1 of aminopropanediol), 54.05 (C2 of aminopropanediol), 63.21 (C3 of aminopropanediol), 97.17 (C1 of D-Glc), 77.79 (C2 of D-Glc), 72.59 (C3 of D-Glc), 70.29 (C4 of D-Glc), 70.50 (C5 of D-Glc), 70.86 (C6 of D-Glc), 63.33 (C1 of Gro), 70.95 (C2 of Gro), 66.40(C3 of Gro) 1H-NMR (in ppm), 4.93 (H1 of D-Gal), 3.73 (H2 of D-Gal), 3.79 (H3 of D-Gal), 3.94 (H4 of D-Gal), 4.24 (H5 of D-Gal), 3.97 (H6 of D-Gal), 3.93 (H6' of D-Gal), 3.66 (H1 of aminopropanediol), 3.74 (H1' of aminopropanediol), 3.41 (H2 of aminopropanediol), 3.96 (H3 of aminopropanediol), 4.03 (H3' of aminopropanediol), 4.94 (H1 of D-Glc), 3.56 (H2 of D-Glc), 3.72 (H3 of D-Glc), 3.29 (H4 of D-Glc), 3.75 (H5 of D-Glc), 4.18 (H6 of D-Glc), 4.36 (H6' of D-Glc), 4.20 (H1 of Gro), 4.42 (H1' of Gro), 5.20 (H2 of Gro), 3.62 (H3 of Gro), 3.78 (H3' of Gro),

Clostridium innocuum(Ref. 0151)




137
alkenyl form of diglycosyl-diradylglycerol
3-O-[2'-a-D-galactopyranosyl-a-D-glucopyranosyl]-2-O-acyl-1-O-alk-1''-enyl-sn-glycerol(Ref. 0152)
EEL0137
Yosuke Koga
Download ChemDraw structure file





Clostridium innocuum(Ref. 0152)




138
alkenyl form of monoglycosyl-diradylglycerol
3-O-a-D-glucopyranosyl-2-O-acyl-1-O-alk-1''-enyl-sn-glycerol(Ref. 0152)
EEL0138
Yosuke Koga
Download ChemDraw structure file





Clostridium innocuum(Ref. 0152)




139
3-O-phytyl-2-O-phytanyl-sn-glycerol(Ref. 0153)/(Ref. 0154)
EEL0139
Yosuke Koga
C43H86O3 651.141 Download ChemDraw structure file




Methanococcoides burtonii(Ref. 0153)/ Halobacterium lacusprofundi(Halorubrum lacusprofundi)(Ref. 0154)




140
3-O-phytanyl-2-O-phytyl-sn-glycerol(Ref. 0153)/(Ref. 0154)
EEL0140
Yosuke Koga
C43H86O3 651.141 Download ChemDraw structure file




Methanococcoides burtonii(Ref. 0153)/ Halobacterium lacusprofundi(Halorubrum lacusprofundi) (Ref. 0154)




141
H-shaped caldarchaeol(Ref. 0155)
EEL0141
Yosuke Koga
C86H170O6 1300.266 Download ChemDraw structure file




Methanothermus fervidus(Ref. 0155)




142
C25,C25-archaetidyl(glucosyl)inositol(Ref. 0156)
2,3-di-O-sesterterpanyl-sn-glycerol-1-phospho-1'-(2'-O-a-D-glucosyl)-myo-inositol(Ref. 0156)
EEL0142
Yosuke Koga
C65H129O16P 1197.684 Download ChemDraw structure file


Aeropyrum pernix(Ref. 0156)




143
C25,C25-archaetidylinositol(Ref. 0156)
2,3-di-O-sesterterpanyl-sn-glycerol-1-phospho-myo-inositol(Ref. 0156)
EEL0143
Yosuke Koga
C59H119O11P 1035.543 Download ChemDraw structure file




Aeropyrum pernix(Ref. 0156)




144
1-O-octadec-9-enylglycerol(Ref. 0157)
EEL0144
Yosuke Koga
C21H42O3 342.556 Download ChemDraw structure file




deep sea shark liver oil (Centrophorus squamosus) (Ref. 0157)




145
1-O-hexadec-9-enylglycerol(Ref. 0157)
EEL0145
Yosuke Koga
C19H38O3 314.503 Download ChemDraw structure file




deep sea shark liver oil (Centrophorus squamosus) (Ref. 0157)




146
HSO3-Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL0146
Yosuke Koga
C98H192O19S 1706.628 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




147
HSO3-Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL0147
Yosuke Koga
C98H190O19S 1704.612 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




148
HSO3-Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL0148
Yosuke Koga
C98H188O19S 1702.596 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




149
HSO3-Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL0149
Yosuke Koga
C98H186O19S 1700.580 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




150
HSO3-Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL0150
Yosuke Koga
C98H184O19S 1698.564 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




151
HSO3-Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL0151
Yosuke Koga
C98H182O19S 1696.548 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




152
HSO3-Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL0152
Yosuke Koga
C98H180O19S 1694.532 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




153
HSO3-Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL0153
Yosuke Koga
C98H178O19S 1692.517 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




154
HSO3-Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL0154
Yosuke Koga
C98H176O19S 1690.501 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




155
HSO3-Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0155
Yosuke Koga
C104H203O27PS 1948.748 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




156
HSO3-Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0156
Yosuke Koga
C104H201O27PS 1946.732 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




157
HSO3-Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0157
Yosuke Koga
C104H199O27PS 1944.716 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




158
HSO3-Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0158
Yosuke Koga
C104H197O27PS 1942.701 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




159
HSO3-Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0159
Yosuke Koga
C104H195O27PS 1940.685 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




160
HSO3-Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0160
Yosuke Koga
C104H193O27PS 1938.669 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




161
HSO3-Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0161
Yosuke Koga
C104H191O27PS 1936.653 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




162
HSO3-Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0162
Yosuke Koga
C104H189O27PS 1934.637 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




163
HSO3-Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0163
Yosuke Koga
C104H187O27PS 1932.621 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




164
HSO3-Glcp-b-1-calditocaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0164
Yosuke Koga
C104H203O27PS 1948.748 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




165
HSO3-Glcp-b-1-calditocaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0165
Yosuke Koga
C104H201O27PS 1946.732 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




166
HSO3-Glcp-b-1-calditocaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0166
Yosuke Koga
C104H199O27PS 1944.716 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




167
HSO3-Glcp-b-1-calditocaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0167
Yosuke Koga
C104H197O27PS 1942.701 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




168
HSO3-Glcp-b-1-calditocaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0168
Yosuke Koga
C104H195O27PS 1940.685 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




169
HSO3-Glcp-b-1-calditocaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0169
Yosuke Koga
C104H193O27PS 1938.669 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




170
HSO3-Glcp-b-1-calditocaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0170
Yosuke Koga
C104H191O27PS 1936.653 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




171
HSO3-Glcp-b-1-calditocaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0171
Yosuke Koga
C104H189O27PS 1934.637 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




172
HSO3-Glcp-b-1-calditocaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL0172
Yosuke Koga
C104H187O27PS 1932.621 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




173
b-D-glucopyranosyl-diglycerol tetraether (Ref. 0159)/ b-D-Glcp-caldarchaeol
EEL0173
Yosuke Koga
GL-IV(Ref. 0159)
C92H178O11 1460.391 Download ChemDraw structure file

molecular rotation +24deg(20 C, in chloroform)
103.6ppm indicates a b-glucosidic linkage



Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




174
b-D-glucopyranosyl-diglycerol tetraether (Ref. 0159)/ b-D-Glcp-caldarchaeol
EEL0174
Yosuke Koga
GL-IV(Ref. 0159)
C92H176O11 1458.375 Download ChemDraw structure file

molecular rotation +24deg(20 C, in chloroform)
103.6ppm indicates a b-glucosidic linkage



Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




175
b-D-glucopyranosyl-diglycerol tetraether (Ref. 0159)/ b-D-Glcp-caldarchaeol
EEL0175
Yosuke Koga
GL-IV(Ref. 0159)
C92H174O11 1456.359 Download ChemDraw structure file

molecular rotation +24deg(20 C, in chloroform)
103.6ppm indicates a b-glucosidic linkage



Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




176
Glcp-b1'-2'Glcp-b1'-1caldarchaeol/b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyldiglycerol tetraether/b-D-Glcp-(1,2)-b-D-Glcp-caldarchaeol(Ref. 0159)
EEL0176
Toshihiro Itoh
GL-III(Ref. 0159)
C98H192O16 1626.563 Download ChemDraw structure file





Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




177
Glcp-b1'-2'Glcp-b1'-1caldarchaeol/b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyldiglycerol tetraether/b-D-Glcp-(1,2)-b-D-Glcp-caldarchaeol(Ref. 0159)
EEL0177
Toshihiro Itoh
GL-III(Ref. 0159)
C98H190O16 1624.548 Download ChemDraw structure file





Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




178
Glcp-b1'-2'Glcp-b1'-1caldarchaeol/b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyldiglycerol tetraether/b-D-Glcp-(1,2)-b-D-Glcp-caldarchaeol(Ref. 0159)
EEL0178
Toshihiro Itoh
GL-III(Ref. 0159)
C98H188O16 1622.532 Download ChemDraw structure file





Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




179
Glcp-b1'-2'Glcp-b1'-1caldarchaeol/b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyldiglycerol tetraether/b-D-Glcp-(1,2)-b-D-Glcp-caldarchaeol(Ref. 0159)
EEL0179
Toshihiro Itoh
GL-III(Ref. 0159)
C98H186O16 1620.516 Download ChemDraw structure file





Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




180
Glcp-b1'-2'Glcp-b1'-1caldarchaeol/b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyldiglycerol tetraether/b-D-Glcp-(1,2)-b-D-Glcp-caldarchaeol(Ref. 0159)
EEL0180
Toshihiro Itoh
GL-III(Ref. 0159)
C98H184O16 1618.500 Download ChemDraw structure file





Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




181
b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyldiglycerol tetraether(Ref. 0159) / b-D-Glcp-(1,2)-b-D-Glcp-(1,2)-b-D-Glcp-caldarchaeol
EEL0181
Toshihiro Itoh
GL-II(Ref. 0159)
C104H202O21 1788.704 Download ChemDraw structure file





Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




182
b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyldiglycerol tetraether(Ref. 0159) / b-D-Glcp-(1,2)-b-D-Glcp-(1,2)-b-D-Glcp-caldarchaeol
EEL0182
Toshihiro Itoh
GL-II(Ref. 0159)
C104H200O21 1786.688 Download ChemDraw structure file





Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




183
b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyldiglycerol tetraether(Ref. 0159) / b-D-Glcp-(1,2)-b-D-Glcp-(1,2)-b-D-Glcp-caldarchaeol
EEL0183
Toshihiro Itoh
GL-II(Ref. 0159)
C104H198O21 1784.672 Download ChemDraw structure file





Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




184
b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyldiglycerol tetraether(Ref. 0159) / b-D-Glcp-(1,2)-b-D-Glcp-(1,2)-b-D-Glcp-caldarchaeol
EEL0184
Toshihiro Itoh
GL-II(Ref. 0159)
C104H196O21 1782.656 Download ChemDraw structure file





Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




185
b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyldiglycerol tetraether(Ref. 0159) / b-D-Glcp-(1,2)-b-D-Glcp-(1,2)-b-D-Glcp-caldarchaeol
EEL0185
Toshihiro Itoh
GL-II(Ref. 0159)
C104H194O21 1780.641 Download ChemDraw structure file





Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




186
b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyl-(1,2)-b-D-glucopyranosylcaldarchaetidyl-myo-inositol(Ref. 0159)/ b-D-Glcp-(1,2)-b-D-Glcp-(1,2)-b-D-Glcp-caldarchaetidyl-myo-inositol(Ref. 0159)
EEL0186
Toshihiro Itoh
GLP-I(Ref. 0159)
C110H213O29P 2030.825 Download ChemDraw structure file





Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




187
b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyl-(1,2)-b-D-glucopyranosylcaldarchaetidyl-myo-inositol(Ref. 0159)/ b-D-Glcp-(1,2)-b-D-Glcp-(1,2)-b-D-Glcp-caldarchaetidyl-myo-inositol(Ref. 0159)
EEL0187
Toshihiro Itoh
GLP-I(Ref. 0159)
C110H211O29P 2028.809 Download ChemDraw structure file





Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




188
b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyl-(1,2)-b-D-glucopyranosylcaldarchaetidyl-myo-inositol(Ref. 0159)/ b-D-Glcp-(1,2)-b-D-Glcp-(1,2)-b-D-Glcp-caldarchaetidyl-myo-inositol(Ref. 0159)
EEL0188
Toshihiro Itoh
GLP-I(Ref. 0159)
C110H209O29P 2026.793 Download ChemDraw structure file





Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




189
b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyl-(1,2)-b-D-glucopyranosylcaldarchaetidyl-myo-inositol(Ref. 0159)/ b-D-Glcp-(1,2)-b-D-Glcp-(1,2)-b-D-Glcp-caldarchaetidyl-myo-inositol(Ref. 0159)
EEL0189
Toshihiro Itoh
GLP-I(Ref. 0159)
C110H207O29P 2024.777 Download ChemDraw structure file





Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




190
b-D-glucopyranosyl-(1,2)-b-D-glucopyranosyl-(1,2)-b-D-glucopyranosylcaldarchaetidyl-myo-inositol(Ref. 0159)/ b-D-Glcp-(1,2)-b-D-Glcp-(1,2)-b-D-Glcp-caldarchaetidyl-myo-inositol(Ref. 0159)
EEL0190
Toshihiro Itoh
GLP-I(Ref. 0159)
C110H205O29P 2022.761 Download ChemDraw structure file





Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




191
unsaturated lysoarchaetidic acid
(S)-3-O-geranylgeranylglycerylphosphate/3-geranylgeranyl-sn-glycerol-1-phosphate/3-(3',7',11',15'-tetramethylhexadec-2',6',10',14'-tetraenyl)-sn-glycerol-1-phosphate
EEL0201
Yosuke Koga
LysoAA/LAA
C23H41O6P 444.542 Download ChemDraw structure file
biosynthetic intermediate




Methanothermobacter marburgensis enzymatic synthesis(Ref. 0174)

biosynthesized from sn-G-1-P and GGPP by GGGPsynthase

192
unsaturated archaetidic acid
2,3-di-O-geranylgeranyl-sn-glycerol-1-phosphate/2,3-di-O-geranylgeranyl-sn-glycerol-1-phosphate/2,3-di-O-(3',7',11',15'-tetramethylhexadec-2',6',10',14'-tetraenyl)-sn-glycerol-1-phosphate
EEL0202
Yosuke Koga
unsaturated AA
C43H73O6P 717.010 Download ChemDraw structure file
biosynthetic intermediate

positive FAB-MS 740(M+Na+H)+, negative FAB-MS 715(M-H)-(Ref. 0166)


Methanothermobacter marburgensis enzymatic synthesis(Ref. 0174)(Ref. 0166)

biosynthesized from GGGP DGGGP synthase


193
CDP-archaeol
cytidine-diphospho-(2,3-di-O-geranylgeranyl-sn-glycerol)/cytidine-diphospho-(2,3-di-O-3',7',11',15'-tetramethylhexadec-2',6',10',14'-tetraenyl)-sn-glycerol
EEL0203
Yosuke Koga
C52H85O13N3P2 1022.191 Download ChemDraw structure file
biosynthetic intermediate

positive FAB-MS 739(M-CMP+Na+H)+, 1021(M)+, 1043(M-H+Na)+, 1065(M-2H+2Na)+(Ref. 0166)

TLC Rf=0.37 chloroform-methanol-NH3 (60:35:8);
Rf=0.40 chloroform-methanol-acetic acid-water(80:30:15:5)(Ref. 0166)
Methanothermobacter thermautotrophicus(Ref. 0166)
biosynthesized from unsaturated AA/CDP-archaeol synthase


194
unsaturated archaetidylserine
2,3-di-O-geranylgeranyl-sn-glycerol-1-phospho-L-serine/2,3-di-O-(3',7',11',15'-tetramethylhexadec-2',6',10',14'-tetraenyl)-sn-glycerol-1-phospho-L-serine
EEL0204
Yosuke Koga
AS
C46H78O8NP 804.087 Download ChemDraw structure file
biosynthetic intermediate

positive FAB-MS 803(M)+, 827(M+Na+H)+, 762(M-serine+Na+H)+, 784(M-serine+3Na)+(Ref. 0175)


Methanothermobacter thermautotrophicus(Ref. 0175)(Ref. 0166)

synthesized from CDP-archaeol and L-serine, AS synthase
MT1027/A69004(Ref. 0175)(Ref. 0178)

195
a-monogeranylgeranylglycerol
(R)-3-O-GGglycerol/3-geranylgeranyl-sn-glycerol/3-(3',7',11',15'-tetramethylhexadec-2',6',10',14'-tetraenyl)-sn-glycerol
EEL0205
Yosuke Koga
C23H40O3 364.562 Download ChemDraw structure file

[a]d-25=-2.3deg (C1.5, CHCl3)(Ref. 0174)
(CCl4)3590, 3454 (Br), 2970, 2924, 2863, 1704, 1648, 1530, 1364, 1310, 1098, 1048, 1027, 809 (Ref. 0174)
1H NMR (300MHz, CDCl3)1.5-1.7 (15H, d, 5 CH3), 1.9-2.1(12H, m, 6 CH2), 3.1(br, H, on hydroxyl), 3.49(2 H, m), 3.62(1 H, dd, J=4.3, 11.8Hz), 3.70(1 H, dd, J=4.3, 11.8Hz), 3.85(1 H, m), 4.0[2H, d, J=6.7Hz, H at C(1) on geranylgeranyl], 5.0-5.13[3H, m, H at C(6), C(10), and C(14) on geranylgeranyl], 5.30[1 H, t, J=6.7Hz, H at C(2) on geranylgeranyl];
13C NMR (75MHz, CDCl3)16.0(q), 16.5(q), 17.7(q), 25.7(q), 26.3(t), 26.6(t), 26.8(t), 39.6(t), 39.68(t), 39.71(t), 64.2(t), 67.9(t), 70.5(d), 71.6(t), 120.3(d), 123.7(d), 124.2(d), 124.4(d), 131.3(s), 135.0(s), 135.4(s), 141.0(s) (Ref. 0174)
(CI, methane) 69(100), 81(29.7), 95(12.9), 109(13.7), 121(15), 135(13.2), 149(7.2), 163(5.2), 175(3), 189(4.2), 211(4), 225(2.6), 253(2.6), 267(3.8), 273(6.1), 351(2.5), 365(M+1, 5.7) (Ref. 0174)

silica gel flash chromatography (Rf=0.30, ethyl acetate-hexane(1:1))(Ref. 0174)
synthetic compound(Ref. 0174)



196
CDP-archaeol
cytidine-diphospho-(2,3-di-O-phytanyl-sn-glycerol)/cytidine-diphospho-(2,3-di-O-3',7',11',15'-tetramethylhexadecyl)-sn-glycerol
EEL0206
Yosuke Koga
C52H101O13N3P2 1038.318 Download ChemDraw structure file


FAB-MS 731(M-CMP)-, 1036(M-H)(Ref. 0166)

TLC Rf=0.37 chloroform-methanol-NH3(60:35:8); Rf=0.40 chloroform-methanol-acetic acid-water (80:30:15:5)(Ref. 0166)
synthetic compound(Ref. 0166)



197
b-monogeranylgeranylglycerol
(R)-2-O-GGglycerol/2-geranylgeranyl-sn-glycerol/2-(3',7',11',15'-tetramethylhexadec-2',6',10',14'-tetraenyl)-sn-glycerol
EEL0207
Yosuke Koga
C23H40O3 364.562 Download ChemDraw structure file

IR(neat) 3450(br), 2965, 2925, 2875, 1710, 1670, 1445, 1380, 1110, 1050, 910, 730(Ref. 0174)
1H NMR (300MHz,CDCl3)1.5-1.7(15H,5CH3), 1.9-2.1(12H,6CH2), 3.5(1H, m), 3.67(2H, dd, J=4.3, 11.6Hz, H of glyceryl methylene), 3.75(2H, dd, J=4.3Hz, 11.6Hz, H of glyceryl methylene), 4.13[2H, d, J=6.7Hz, H at C(1) on geranylgeranyl], 5.08[3H, m, H at C(6), C(10) and C(14) on geranylgeranyl], 5.35[1H, t, J=6.7Hz H at C(2) on geranylgeranyl]
13C NMR(75MHz,CDCl3)16.1(q), 16.7(q), 17.8(q), 25.8(q), 26.3(t), 26.7(t), 26.8(t), 39.6(t), 39.7(t), 39.8(t), 62.4(t), 66.4(t), 78.7(d), 120.4(d), 123.6(d), 124.1(d), 124.3(d), 131.2(s), 134.9(s), 135.4(s), 141.0(s)(Ref. 0174)
(EI 17eV)69(100), 81(99), 93(50), 107(25.8), 121(32.8), 135(37.5), 149(9.0), 161(6.6), 175(2.7), 189(3.4), 203(6.3), 215(1.4), 229(2.9), 243(1.1), 257(1.9), 272(2.5), 364(M+, 1.2)(Ref. 0174)

TLC Rf=0.30, ethyl acetate-hexane(1:1)(Ref. 0174)
synthetic compound(Ref. 0174)



198
(S)-1,2-O-Isopropylidene-3-O-geranylgeranylglycerol
EEL0208
Yosuke Koga
C25H41O3 389.591 Download ChemDraw structure file

[a]d-25=+7.5deg (C0.83, CHCl3)(Ref. 0174)
1H NMR (300MHz,CDCl3)1.33(3H, s, CH3), 1.42(3H, s, CH3), 1.55-1.65(15H, m, 5CH3 on geranylgeranyl), 1.9-2.1(12H, br m, 6CH2 on geranylgeranyl), 3.38-3.68(3H, br m), 4.0-4.1(3H, m), 4.23-4.3(1H, m), 5.08[3H, br m, H at C(6), C(10) and C(14) on geranylgeranyl], 5.3[1H, t, J=6.8Hz H at C(2) on geranylgeranyl]
13C NMR(75MHz,CDCl3)16.1(q), 16.6(q), 17.8(q), 25.5(q), 25.8(q), 26.4(t), 26.7(t), 26.87(t), 26.93(q), 39.7(t), 39.81(t), 39.87(t), 67.1(t), 68.1(t), 71.1(t), 74.9(d), 109.5(s), 120.7(d), 123.9(d), 124.3(d), 124.5(d), 131.4(s), 135.1(s), 135.4(s), 140.6(s)(Ref. 0174)
(EI 70eV)69(100), 93(22), 121(10.6), 135(15.9), 161(5.7), 175(2.9), 189(1.9), 203(2.9), 225(2.4), 272(3.9), 389(M-CH3, 2.1), 404(M+, 0.7)(Ref. 0174)

silica gel flash chromatography (Rf=0.35, ethyl acetate-hexane(2:23) )(Ref. 0174)
synthetic compound(Ref. 0174)



199
(S)-1-O-(tert-butyldimethylsilyl)-2-O-geranylgeranyl-3-O-benzylglycerol
EEL0209
Yosuke Koga
C36H60O3Si 568.945 Download ChemDraw structure file

[a]d-25=-2.4deg (C3.2, CHCl3)(Ref. 0174)
1H NMR (300MHz,CDCl3) 0.1(6H, s, 2CH3 on Si), 0.9(9H, s, 3CH3 on tert-butyl), 1.55-1.7(15H, m, 5CH3 on geranylgeranyl), 1.95-3.15(12H, br m, 6CH2 on geranylgeranyl), 3.45-3.70(5H, br m), 4.18[2H, d, J=6.7Hz H at C(1) on geranylgeranyl], 4.58(2H, s, CH2), 5.0-5.2[3H m, H at C(6), C(10) and C(14)], 5.4 [1H, t, J=6.7Hz H at C(2) on geranylgeranyl], 7.25(5H, br m)
13C NMR(75MHz, CDCl3)-5,2(q), 16.0(q), 16.5(q), 17.7(q), 18.2(q), 18.5(s), 25.2(q), 25.9(q), 26.37(t), 26.44(t), 27.8(t), 39.6(t), 39.7(t), 63.0(t), 66.9(t), 70.2(t), 73.5(t), 78.5(d), 121.2(d), 123.9(d), 124.2(d), 124.4(d), 127.46(d), 127.50(d), 128.3(d), 128.5(s), 132.0(s), 134.9(s), 135.2(s), 139.7(s)(Ref. 0174)
(CI methane) 69(61.9), 81(40.9), 91(90.9), 109(15.5), 121(15.1), 137(18.9), 149(15.7), 163(7.4), 175(3.3), 189(8.6), 217(9.1), 239(11.4), 257(2.2), 273(19.4), 297(100), 568(M+1, 2.0)(Ref. 0174)

chromatography on silica (Rf=0.57, ethyl acetate-hexane(2:23) )(Ref. 0174)
synthetic compound(Ref. 0174)



200
(S)-1-O-(tert-butyldimethylsilyl)-2-O-geranylgeranylglycerol
EEL0210
Yosuke Koga
C29H54O3Si 478.823 Download ChemDraw structure file

[a]d-25= -13.9deg (C3, CHCl3)(Ref. 0174)
1H NMR (300MHz,CDCl3) 0.1(6H, s, 2CH3 on Si), 0.95(9H, s, 3CH3 on tert-butyl), 1.6-1.75(15H, m, 5CH3 on geranylgeranyl), 2.1-2.3(12H, br m, 6CH2 on geranylgeranyl), 3.5-3.85(5H, m), 4.15[1H, dd, J=5.9, 11.2Hz H at C(1) on geranylgeranyl], 4.24[1H, dd, J=5.9, 11.2Hz H at C(1) on geranylgeranyl], 5.12[3H, m, H at C(6), C(10) and C(14) on geranylgeranyl], 5.45 [1H, t, J=5.9Hz, H at C(2) on geranylgeranyl],
13C NMR(75MHz, CDCl3)-5,2(q), 16.0(q), 16.5(q), 17.7(q), 18.2(q), 18.5(s), 25.7(q), 25.8(q), 26.3(t), 26.6(t), 26.7(t), 39.6(t), 39.67(t), 39.70(t), 63.0(t), 63.1(t), 66.6(t), 78.9(d), 120.7(d), 123.8(d), 124.1(d), 124.3(d), 131.3(s), 134.9(s), 135.4(s), 140.5(s)(Ref. 0174)
(EI 70eV) 69(100), 81(99), 93(59.8), 107(39), 121(62.9), 137(99), 149(44), 161(10.8), 189(11.6), 203(31.5), 229(5.5), 257(3.1), 272(8.4), 478(M+, 1.6)(Ref. 0174)

chromatography on silica (Rf= 0.36, ethyl acetate-hexane(15:85) )(Ref. 0174)
synthetic compound(Ref. 0174)




201
(S)-1-O-(tert-butyldimethylsilyl)-2,3-di-O-geranylgeranylglycerol
EEL0211
Yosuke Koga
C49H86O3Si 751.291 Download ChemDraw structure file

1H NMR (300MHz,CDCl3) 0.10(6H, s, 2CH3 on Si), 0.85(9H, s, 3CH3 on tert-butyl), 1.55-1.75(30H, m, 10CH3 on geranylgeranyl), 1.95-2.15(24H, br m, 12CH2 on geranylgeranyl), 3.44-3.65(5H, m), 3.95(2H, d, J=6.6Hz), 4.13(2H, d, J=6.8Hz), 5.05(6H, br m), 5.36(2H, m)
13C NMR(75MHz, CDCl3)-5,2(q), 16.1(q), 16.7(q), 17.8(q), 18.4(q), 25.8(q), 26.0(q), 26.5(t), 26.8(t), 26.9(t), 39.7(t), 38.8(t), 63.1(t), 67.0(t), 70.8(t), 73.4(t), 78.6(d), 121.3(d), 123.9(d), 124.1(d), 124.3(d), 127.4(d), 127.5(d), 128.2(d), 131.1(s), 134.8(s), 135.1(s), 138.4(s),139.6(s)(Ref. 0174)
(CI, methane) 69(100), 81(68.4), 93(29.9), 107(13.8), 123(26.3), 135(13), 149(15.5), 161(7.5), 171(4.6), 189(11.3), 207(34.9), 217(11.1), 273(18.4), 477(18.8), 545(2.5), 750(M+1, 1.3)(Ref. 0174)

TLC (Rf= 0.15 ethyl acetate-hexane(1:50))(Ref. 0174)
synthetic compound(Ref. 0174)



202
unsaturated benzylarchaeol
2,3-di-O-geranylgeranyl-1-benzyl-sn-glycerol/2,3-di-O-(3',7',11',15'-tetramethylhexadec-2',6',10',14'-tetraenyl)-1-benzyl-sn-glycerol
EEL0212
Yosuke Koga
C50H78O3 727.153 Download ChemDraw structure file





synthetic compound(Ref. 0166)



203
1,2-di-O-geranylgeranyl-3-benzyl-sn-glycerol/1,2-di-O-(3',7',11',15'-tetramethylhexadec-2',6',10',14'-tetraenyl)-3-benzyl-sn-glycerol
EEL0213
Yosuke Koga
C50H78O3 727.153 Download ChemDraw structure file





synthetic compound(Ref. 0166)



204
benzylarchaeol
2,3-di-O-phytyl-1-benzyl-sn-glycerol/2,3-di-O-(3',7',11',15'-tetramethylhexadec-2'-enyl)-1-benzyl-sn-glycerol
EEL0214
Yosuke Koga
C50H90O3 739.248 Download ChemDraw structure file





synthetic compound(Ref. 0166)



205
2,3-di-O-oleyl-1-benzyl-sn-glycerol/2,3-di-O-(9'-cis-octadecenyl)-sn-glycerol
EEL0215
Yosuke Koga
C46H82O3 683.141 Download ChemDraw structure file





synthetic compound(Ref. 0166)



206
unsaturated archaeol
(R)-2,3-di-O-geranylgeranylglycerol/2,3-di-O-geranylgeranyl-sn-glycerol/2,3-di-O-(3',7',11',15'-tetramethyl-2',6',10',14'-tetraenyl)-sn-glycerol
EEL0216
Yosuke Koga
C43H72O3 637.030 Download ChemDraw structure file

[a]D= +9.6deg (Ref. 0166)/[a]d-25= -1.2deg (C0.83, CHCl3)(Ref. 0174)
1H NMR (300MHz,CDCl3) 1.55-1.75(30H, m, 10CH3), 1.90-2.15(24H, br m, 12CH2), 3.43-3.55(4H, m), 3.67-3.76(1H, m), 3.98-4.01[2H, d, J=6.8Hz, H at C(1) of geranylgeranyl at glyceryl C(3)], 4.05-4.11[1H, dd, J=7.1, 12.8Hz, H at C(1) of geranylgeranyl at glyceryl C(2)], 4.14-4.20[1H, dd, J=7.1, 12.8Hz, H at C(1) of geranylgeranyl at glyceryl C(2)], 5.15(6H, m), 5.4(2H, m)
13C NMR(75MHz, CDCl3) 16.1(q), 16.60(q), 16.63(q), 17.8(q), 25.8(q), 26.4(q), 26.5(t), 26.7(t), 26.9(t), 29.8(t), 39.7(t), 39.76(t), 39.78(t), 63.2(t), 66.6(t), 68.0(t), 70.1(t), 77.5(d), 120.5(d), 120.8(d), 123.8(d), 124.2(d), 124.4(d), 131.2(s), 134.9(s), 135.30(s), 135.32(s), 140.5(s)(Ref. 0174)
(EI 7eV) 69(100), 81(99), 93(89), 103(47.6), 107(55.5), 121(60.2), 135(65.6), 147(28.1), 161(25.4), 177(7.8), 191(4.7), 203(25.6), 229(3.1), 257(2.3), 272(25.8), 363(26.5), 636(M+, 0.5)(Ref. 0174)

TLC Rf= 0.22 ethyl acetate-hexane (3:22)
Methanopyrus kandleri(Ref. 0166)(Ref. 0167)(Ref. 0176)



207
1,2-di-O-geranylgeranyl-sn-glycerol/1,2-di-O-(3',7',11',15'-tetramethyl-2',6',10',14'-tetraenyl)-sn-glycerol
EEL0217
Yosuke Koga
C43H72O3 637.030 Download ChemDraw structure file

[a]D= -9.7deg (Ref. 0166)




synthetic compound(Ref. 0166)



208
2,3-di-O-phytyl-sn-glycerol/2,3-di-O-(3',7',11',15'-tetramethyl-2'-hexadecyl)-sn-glycerol
EEL0218
Yosuke Koga
C43H84O3 649.125 Download ChemDraw structure file





synthetic compound(Ref. 0166)



209
2,3-di-O-oleyl-sn-glycerol/2,3-di-O-(9'-cis-octadecenyl)-sn-glycerol
EEL0219
Yosuke Koga
C39H76O3 593.019 Download ChemDraw structure file





synthetic compound(Ref. 0166)



210
2,3-di-O-geranylgeranyl-1-(dimethylphospho)-sn-glycerol/2,3-di-O-(3',7',11',15'-tetramethylhexadec-2',6',10',14'-tetraenyl)-1-(dimethylphospho)-sn-glycerol
EEL0220
Yosuke Koga
C45H77O6P 745.063 Download ChemDraw structure file





synthetic compound(Ref. 0166)



211
1,2-di-O-geranylgeranyl-3-(dimethylphospho)-sn-glycerol/1,2-di-O-(3',7',11',15'-tetramethylhexadec-2',6',10',14'-tetraenyl)-3-(dimethylphospho)-sn-glycerol
EEL0221
Yosuke Koga
C45H77O6P 745.063 Download ChemDraw structure file





synthetic compound(Ref. 0166)



212
2,3-di-O-phytyl-1-(dimethylphospho)-sn-glycerol/2,3-di-O-(3',7',11',15'-tetramethylhexadec-2'-enyl)-1-(dimethylphospho)-sn-glycerol
EEL0222
Yosuke Koga
C45H89O6P 757.158 Download ChemDraw structure file





synthetic compound(Ref. 0166)



213
2,3-di-O-oleyl-1-(dimethylphospho)-sn-glycerol/2,3-di-O-(9'-cis-octadecenyl)-1-(dimethylphospho)-sn-glycerol
EEL0223
Yosuke Koga
C41H81O6P 701.052 Download ChemDraw structure file





synthetic compound(Ref. 0166)



214
1,2-di-O-geranylgeranyl-sn-glycerol-3-phosphate/1,2-di-O-(3',7',11',15'-tetramethylhexadec-2',6',10',14'-tetraenyl)-sn-glycerol-3-phosphate
EEL0224
Yosuke Koga
C43H73O6P 717.010 Download ChemDraw structure file


positive FAB-MS 740(M+Na+H)+, negative FAB-MS 715(M-H)-(Ref. 0166)


synthetic compound(Ref. 0166)



215
unsaturated archaetidic acid
2,3-di-O-phytyl-sn-glycerol-1-phosphate/2,3-di-O-(3',7',11',15'-tetramethylhexadec-2'-enyl)-sn-glycerol-1-phosphate
EEL0225
Yosuke Koga
C43H85O6P 729.105 Download ChemDraw structure file


FAB-MS 752(M+Na+H)+(Ref. 0166)


synthetic compound(Ref. 0166)



216
2,3-di-O-oleyl-sn-glycerol-1-phosphate/2,3-di-O-(9'-cis-octadecenyl)-sn-glycerol-1-phosphate
EEL0226
Yosuke Koga
C39H77O6P 672.999 Download ChemDraw structure file


FAB-MS 695(M+Na)+(Ref. 0166)


synthetic compound(Ref. 0166)




217
2,3-di-O-phytanyl-1-(diphenylphospho)-sn-glycerol/2,3-di-O-(3',7',11',15'-tetramethylhexadecyl)-1-sn-glycerol
EEL0227
Yosuke Koga
C55H97O6P 885.329 Download ChemDraw structure file





synthetic compound(Ref. 0166)



218
CDP-digeranylgeranylglycerol
cytidine-diphospho-(1,2-di-O-geranylgeranyl)-sn-glycerol/cytidine-diphospho-(1.2-di-O-3',7',11',15'-tetramethylhexadec-2',6',10',14'-tetraenyl)-sn-glycerol
EEL0228
Yosuke Koga
C52H86O13N3P2 1023.199 Download ChemDraw structure file









219
CDP-1,2-dioleylglycerol
cytidine-diphospho-(1,2-di-O-oleyl)-sn-glycerol/cytidine-diphospho-(1,2-di-O-9'-cis-octadecenyl-sn-glycerol)
EEL0229
Yosuke Koga
C48H90O13N3P2 979.188 Download ChemDraw structure file





synthetic compound(Ref. 0175)



220
archaetidylcholine (mixed hydrocarbon)
2,3-di-O-alkyl-sn-glycerol-1-phosphocholine
EEL0230
Yosuke Koga
Download ChemDraw structure file


FAB-MS 818, 781, 536, 240, 224, 840, 816, 538, 308, 256
[Spectrum 0058] (Ref. 0167)
[Spectrum 0057]

TLC Rf=0.20 chloroform-methanol-acetone-acetic acid-water(6:2:8:2:1) (Ref. 0167)
Methanopyrus kandleri(Ref. 0167)




221
archaetidylcholine
2,3-di-O-phytanyl-sn-glycerol-1-phosphocholine/2,3-di-O-(3',7',11',15'-tetramethylhexadecanyl)-sn-glycerol-1-phosphocholine
EEL0231
Yosuke Koga
C48H106O6NP 824.332 Download ChemDraw structure file


FAB-MS 818(M+H)+, 781(M+Na-N(CH3)3)+, 536(M-C20H41)+, 240(M+H-C20H41-OC20H41)+, 224(M+H-2(OC20H41))+, 840(M+Na)+(Ref. 0167)

TLC Rf=0.20 chloroform-methanol-acetone-acetic acid-water(6:2:8:2:1) (Ref. 0167)
Methanopyrus kandleri(Ref. 0167)




222
b-D-gulosylcaldarchaeol
EEL0232
Yosuke Koga
GL-1a
C92H178O11 1460.391 Download ChemDraw structure file




TLC Rf=0.52 chloroform-methanol-1M NH4OH (65:35:5):
[Chromatogram 0025] (Ref. 0170)
[Chromatogram 0026] (Ref. 0170)
Thermoplasma acidophilum(Ref. 0170)




223
a-D-glucosylcaldarchaeol
EEL0233
Yosuke Koga
GL-1b
C92H182O11 1464.423 Download ChemDraw structure file




TLC Rf=0.76 chloroform-methanol-1M NH4OH (65:35:5):
[Chromatogram 0025] (Ref. 0170)
[Chromatogram 0026] (Ref. 0170)
Thermoplasma acidophilum(Ref. 0170)




224
1-(b-D-gulosyl)-1'-(b-D-gulosyl)-caldarchaeol
EEL0234
Yosuke Koga
GL-2a
C98H188O16 1622.532 Download ChemDraw structure file


TLC Rf=0.17 chloroform-methanol-1M NH4OH (65:35:5):
[Chromatogram 0025] (Ref. 0170)
[Chromatogram 0026] (Ref. 0170)
Thermoplasma acidophilum(Ref. 0170)




225
1-(b-D-gulosyl)-1'-(a-D-glucosyl)-caldarchaeol
EEL0235
Yosuke Koga
GL-2b
C98H188O16 1622.532 Download ChemDraw structure file



TLC Rf=0.33 chloroform-methanol-1M NH4OH (65:35:5):
[Chromatogram 0025] (Ref. 0170)
[Chromatogram 0026] (Ref. 0170)
Thermoplasma acidophilum(Ref. 0170)




226
1-(a-D-glucosyl)-1'-(a-D-glucosyl)-caldarchaeol
EEL0236
Yosuke Koga
GL-2c
C98H188O16 1622.532 Download ChemDraw structure file




TLC Rf=0.56 chloroform-methanol-1M NH4OH (65:35:5):
[Chromatogram 0025] (Ref. 0170)
[Chromatogram 0026] (Ref. 0170)
Thermoplasma acidophilum(Ref. 0170)




227
a-D-glucosylcaldarchaetidylglycerol
EEL0237
Yosuke Koga
GPL-K
C95H187O16P 1616.465 Download ChemDraw structure file

1H NMR 13C NMR(Ref. 0171)
FAB-MS 1614(M-H)-, 1452(M-hexose)-(Ref. 0171)

boronic acid-impregnated silica gel HPTLC
Rf= 0.26 chloroform-methanol-NH3(65:35:5):
[Chromatogram 0027] (Ref. 0171)
Thermoplasma acidophilum(Ref. 0171)




228
b-D-gulosylcaldarchaeol
EEL0238
Yosuke Koga
U4
C92H182O11 1464.423 Download ChemDraw structure file




Thermoplasma acidophilum(Ref. 0168)




229
1-b-D-gulosyl-1'-b-D-gulosyl-caldarchaeol
EEL0239
Yosuke Koga
A2
C98H184O16 1618.500 Download ChemDraw structure file

SIMS 1616.9(M-H)-(Ref. 0168)

HPLC-evaporative light-scattering detection:
[Chromatogram 0029] (Ref. 0168)
HPTLC:
[Chromatogram 0028] (Ref. 0168)
Thermoplasma acidophilum(Ref. 0168)




230
b-D-gulosylcaldarchaetidylglycerol
EEL0240
Yosuke Koga
A3
C95H189O16P 1618.481 Download ChemDraw structure file

SIMS 1616.9(M-H)-(Ref. 0168)

HPLC-evaporative light-scattering detection:
[Chromatogram 0029] (Ref. 0168)
HPTLC:
[Chromatogram 0028] (Ref. 0168)
Thermoplasma acidophilum(Ref. 0168)




231
b-D-gulosylcaldarchaetidylglycerol
EEL0241
Yosuke Koga
A4-1
C95H183O16P 1612.434 Download ChemDraw structure file

SIMS 1609.9(M-H)-(Ref. 0168)

HPLC-evaporative light-scattering detection:
[Chromatogram 0029] (Ref. 0168)
HPTLC:
[Chromatogram 0028] (Ref. 0168)
Thermoplasma acidophilum(Ref. 0168)




232
a-mannosyl(1-3)-b-gulosylcaldarchaeol
EEL0242
Yosuke Koga
A4-2
C98H188O16 1622.532 Download ChemDraw structure file

SIMS 1620.7(M-H)-(Ref. 0168)

HPLC-evaporative light-scattering detection:
[Chromatogram 0029] (Ref. 0168)
HPTLC:
[Chromatogram 0028] (Ref. 0168)
Thermoplasma acidophilum(Ref. 0168)




233
1-a-mannosyl-(1-3)-b-gulosyl-1'-b-gulosylcaldarchaeol
EEL0243
Yosuke Koga
A5
C104H196O21 1782.656 Download ChemDraw structure file



HPLC-evaporative light-scattering detection:
[Chromatogram 0029] (Ref. 0168)
HPTLC:
[Chromatogram 0028] (Ref. 0168)
Thermoplasma acidophilum(Ref. 0168)




234
a-D-mannosyl-(1-3)-a-D-mannosyl-(1-3)-b-gulosyl-caldarchaeol
EEL0244
Yosuke Koga
A6
C104H196O21 1782.656 Download ChemDraw structure file

SIMS 1786.0(M-H)- (cyclopentane ring, 0)(Ref. 0168)

HPLC-evaporative light-scattering detection:
[Chromatogram 0029] (Ref. 0168)
HPTLC:
[Chromatogram 0028] (Ref. 0168)
Thermoplasma acidophilum(Ref. 0168)




235
trimannosyl-glucosylcaldarchaeol
EEL0245
Yosuke Koga
A7
C110H212O26 1950.845 Download ChemDraw structure file

SIMS 1946.3(M-H)-(Ref. 0168)

HPLC-evaporative light-scattering detection:
[Chromatogram 0029] (Ref. 0168)
HPTLC:
[Chromatogram 0028] (Ref. 0168)
Thermoplasma acidophilum(Ref. 0168)




236
a-D-mannosyl-(1-3)-b-D-gulosylcaldarchaetidylglycerol
EEL0246
Yosuke Koga
C2
C101H193O21P 1774.574 Download ChemDraw structure file

SIMS 1771.3(M-H)-(Ref. 0168)

HPLC-evaporative light-scattering detection:
[Chromatogram 0029] (Ref. 0168)
HPTLC:
[Chromatogram 0028] (Ref. 0168)
Thermoplasma acidophilum(Ref. 0168)




237
a-D-mannosyl-(1-3)-a-D-mannosyl-(1-3)-b-D-gulosylcaldarchaetidylglycerol
EEL0247
Yosuke Koga
C3
C107H205O26P 1938.731 Download ChemDraw structure file

SIMS 1933.7(M-H)-(Ref. 0168)

HPLC-evaporative light-scattering detection:
[Chromatogram 0029] (Ref. 0168)
HPTLC:
[Chromatogram 0028] (Ref. 0168)
Thermoplasma acidophilum(Ref. 0168)




238
a-D-mannosyl-(1-3)-a-D-mannosyl-(1-3)-a-D-mannosyl-(1-3)-b-D-gulosylcaldarchaetidylglycerol
EEL0248
Yosuke Koga
C5
C113H217O31P 2102.887 Download ChemDraw structure file

SIMS 2098.9(M-H)-(Ref. 0168)

HPLC-evaporative light-scattering detection:
[Chromatogram 0029] (Ref. 0168)
HPTLC:
[Chromatogram 0028] (Ref. 0168)
Thermoplasma acidophilum(Ref. 0168)




239
2-(3'-sulfo-b-D-galactosyl-(1-6)-b-D-mannosyl)-6-archaetidyl-a-D-glucosylarchaeol/3-HSO3-Galp-b1,6Manp-a1,2Glcp-a1,1-[sn-2,3-di-O-phytanylglycerol]-6-[phospho-sn-2,3-di-O-phytanylglycerol
EEL0249
Yosuke Koga
Lipid X
C104H205O26PS 1934.765 Download ChemDraw structure file

1H NMR(Ref. 0173)
13C NMR(Ref. 0173)
31P NMR(Ref. 0173)
ESI-MS 1933.7(M-H)-, 966.0(M-2H)2-, 1955.4(M-2H+Na)-, 1853.8(M-SO3)-

[Spectrum 0060] (Ref. 0173)

TLC Rf= 0.21 chloroform-methanol-90% acetic acid(65:4:35):
[Chromatogram 0030] (Ref. 0173)
Halobacterium salinarum L33 purple membrane(Ref. 0173)




240
1,3-diarchaetidylglycerol/diether analog of cardiolipin /sn-2,3-di-O-phytanyl-1-phosphoglycerol-3-phospho-sn-2,3-di-O-phytanylglycerol
1,3-di-O-(2',3'-di-O-phytanyl-sn-glycerophosphoryl)-glycerol/1,3-di-O-(2',3'-di-O-(3'',7'',11'',15''-tetramethylhexadecyl)-sn-glycerophosphoryl)-glycerol
EEL0250
Yosuke Koga
Lipid Y
C89H182O13P2 1522.337 Download ChemDraw structure file

ESI-MS 1521.3(M-H)-, 760.0(M-2H)2-:
[Spectrum 0062] (Ref. 0173)

TLC Rf= 0.94 chloroform-methanol-90% acetic acid(65:4:35):
[Chromatogram 0030] (Ref. 0173)
Halobacterium salinarum L33 purple membrane(Ref. 0173)




241
crenarchaeol
EEL0251
Yosuke Koga
C86H162O6 1292.203 Download ChemDraw structure file

13C and 1H-NMR(Ref. 0177)

holocene sediments/ancient sediments(Ref. 0169)




242
tetraether lipid X
EEL0252
Yosuke Koga
C66H132O6 1021.751 Download ChemDraw structure file



holocene sediments/ancient sediments(Ref. 0169)




243
tetraether lipid XI
EEL0253
Yosuke Koga
C67H134O6 1035.777 Download ChemDraw structure file



holocene sediments/ancient sediments(Ref. 0169)




244
tetraether lipid XII
EEL0254
Yosuke Koga
C68H136O6 1049.804 Download ChemDraw structure file



holocene sediments/ancient sediments(Ref. 0169)




245
tetraether lipid XIII
EEL0255
Yosuke Koga
C66H130O6 1019.735 Download ChemDraw structure file




holocene sediments/ancient sediments(Ref. 0169)




246
tetraether lipid XIV
EEL0256
Yosuke Koga
C66H128O6 1017.719 Download ChemDraw structure file




holocene sediments/ancient sediments(Ref. 0169)




247
tetraether lipid XV
EEL0257
Yosuke Koga
C78H156O6 1190.070 Download ChemDraw structure file




holocene sediments/ancient sediments(Ref. 0169)




248
crenarchaeol : regioisomer
EEL0258
Yosuke Koga
C86H162O6 1292.203 Download ChemDraw structure file










249
Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL1001
Toshihiro Itoh
C98H190O16 1624.548 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




250
Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL1002
Toshihiro Itoh
C98H188O16 1622.532 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




251
Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL1003
Toshihiro Itoh
C98H186O16 1620.516 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




252
Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL1004
Toshihiro Itoh
C98H184O16 1618.500 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




253
Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL1005
Toshihiro Itoh
C98H182O16 1616.484 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




254
Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL1006
Toshihiro Itoh
C98H180O16 1614.468 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




255
Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL1007
Toshihiro Itoh
C98H178O16 1612.452 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




256
Glcp-b-Galp-b1'-1-caldarchaeol(Ref. 0072/0107/0108/0116/0117/0118/0119/0077/0120/0158)
EEL1008
Toshihiro Itoh
C98H176O16 1610.436 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




257
Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL1009
Toshihiro Itoh
C104H201O24P 1866.668 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




258
Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL1010
Toshihiro Itoh
C104H199O24P 1864.652 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




259
Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL1011
Toshihiro Itoh
C104H197O24P 1862.636 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




260
Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL1012
Toshihiro Itoh
C104H195O24P 1860.620 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




261
Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL1013
Toshihiro Itoh
C104H193O24P 1858.605 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




262
Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL1014
Toshihiro Itoh
C104H191O24P 1856.589 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




263
Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL1015
Toshihiro Itoh
C104H189O24P 1854.573 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




264
Glcp-b-Galp-b-caldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL1016
Toshihiro Itoh
C104H187O24P 1852.557 Download ChemDraw structure file

core lipid (Ref. 0134)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0137/0140/0132)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




265
Glcp-b-calditolcaldarchaeol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0142)
EEL1017
Toshihiro Itoh
C98H190O16 1624.548 Download ChemDraw structure file

core lipid(Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




266
Glcp-b-calditolcaldarchaeol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0142)
EEL1018
Toshihiro Itoh
C98H188O16 1622.532 Download ChemDraw structure file

core lipid(Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




267
Glcp-b-calditolcaldarchaeol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0142)
EEL1019
Toshihiro Itoh
C98H186O16 1620.516 Download ChemDraw structure file

core lipid(Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




268
Glcp-b-calditolcaldarchaeol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0142)
EEL1020
Toshihiro Itoh
C98H184O16 1618.500 Download ChemDraw structure file

core lipid(Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




269
Glcp-b-calditolcaldarchaeol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0142)
EEL1021
Toshihiro Itoh
C98H182O16 1616.484 Download ChemDraw structure file

core lipid(Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




270
Glcp-b-calditolcaldarchaeol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0142)
EEL1022
Toshihiro Itoh
C98H180O16 1614.468 Download ChemDraw structure file

core lipid(Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




271
Glcp-b-calditolcaldarchaeol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0142)
EEL1023
Toshihiro Itoh
C98H178O16 1612.452 Download ChemDraw structure file

core lipid(Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




272
Glcp-b-calditolcaldarchaeol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0142)
EEL1024
Toshihiro Itoh
C98H176O16 1610.436 Download ChemDraw structure file

core lipid(Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0131)/ Sulfolobus solfataricus (Ref. 0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




273
Glcp-b-1-calditolcaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL1025
Toshihiro Itoh
C104H201O24P 1866.668 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




274
Glcp-b-1-calditolcaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL1026
Toshihiro Itoh
C104H199O24P 1864.652 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




275
Glcp-b-1-calditolcaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL1027
Toshihiro Itoh
C104H197O24P 1862.636 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




276
Glcp-b-1-calditolcaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL1028
Toshihiro Itoh
C104H195O24P 1860.620 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




277
Glcp-b-1-calditolcaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL1029
Toshihiro Itoh
C104H193O24P 1858.605 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




278
Glcp-b-1-calditolcaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL1030
Toshihiro Itoh
C104H191O24P 1856.589 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




279
Glcp-b-1-calditolcaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL1031
Toshihiro Itoh
C104H189O24P 1854.573 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




280
Glcp-b-1-calditolcaldarchaetidyl-myo-inositol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077/0158)
EEL1032
Toshihiro Itoh
C104H187O24P 1852.557 Download ChemDraw structure file

core lipid (Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




281
HSO3-O-Glcp-b-calditocaldarchaeol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077)
EEL1033
Toshihiro Itoh
C98H190O19S 1704.612 Download ChemDraw structure file

core lipid(Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




282
HSO3-O-Glcp-b-calditocaldarchaeol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077)
EEL1034
Toshihiro Itoh
C98H188O19S 1702.596 Download ChemDraw structure file

core lipid(Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




283
HSO3-O-Glcp-b-calditocaldarchaeol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077)
EEL1035
Toshihiro Itoh
C98H186O19S 1700.580 Download ChemDraw structure file

core lipid(Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




284
HSO3-O-Glcp-b-calditocaldarchaeol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077)
EEL1036
Toshihiro Itoh
C98H184O19S 1698.564 Download ChemDraw structure file

core lipid(Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




285
HSO3-O-Glcp-b-calditocaldarchaeol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077)
EEL1037
Toshihiro Itoh
C98H182O19S 1696.548 Download ChemDraw structure file

core lipid(Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




286
HSO3-O-Glcp-b-calditocaldarchaeol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077)
EEL1038
Toshihiro Itoh
C98H180O19S 1694.532 Download ChemDraw structure file

core lipid(Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




287
HSO3-O-Glcp-b-calditocaldarchaeol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077)
EEL1039
Toshihiro Itoh
C98H178O19S 1692.517 Download ChemDraw structure file

core lipid(Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




288
HSO3-O-Glcp-b-calditocaldarchaeol(Ref. 0070/0072/0107/0108/0116/0117/0118/0119/0120/0077)
EEL1040
Toshihiro Itoh
C98H176O19S 1690.501 Download ChemDraw structure file

core lipid(Ref. 0126)
hydrocarbon chain (Ref. 0071/0117/0135/0136),core lipid (Ref. 0136/0132/0126)
hydrocarbon chain (Ref. 0071/0139/0137/0138)


Sulfolobus acidocaldarius(Ref. 0071/0125/0126/0128/0129/0131)/ Sulfolobus solfataricus (Ref. 0109/0132/0130)/Desulfurolobus ambivalens(Ref. 0108)




289
b-D-glucopyranosyl-diglycerol tetraether/ b-D-Glcp-caldarchaeol (Ref. 0145/0159)
EEL1041
Toshihiro Itoh
GL-1(Ref. 0145)
C92H180O11 1462.407 Download ChemDraw structure file

molecular rotation +24deg(20 C, in chloroform)
103.6ppm indicates a b-glucosidic linkage



Thermoproteus tenax(Ref. 0145), Pyrobaculum islandicum(Ref. 0159), Pyrobaculum organotrophicum(Ref. 0159)




290
gentiobiosylcaldarchaeol(Ref. 0070/0099/0100/0101/0102)/Glcp-b1'-6'Glcp-b1'-1caldarchaeol/b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyldiglycerol tetraether(Ref. 1005) / b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyl caldarchaeol
EEL1042
Toshihiro Itoh
Gen-CAOH/GL-3(Ref. 0145)
C98H190O16 1624.548 Download ChemDraw structure file

4000-800 cm-1(Ref. 0086)




Thermoproteus tenax(Ref. 0145)




291
b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyldiglycerol tetraether(Ref. 0145) / b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyl caldarchaeol
EEL1043
Toshihiro Itoh
GL-4(Ref. 0145)
C104H200O21 1786.688 Download ChemDraw structure file





Thermoproteus tenax(Ref. 0145)




292
b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyldiglycerol tetraether(Ref. 0145) / b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyl caldarchaeol
EEL1044
Toshihiro Itoh
GL-4(Ref. 0145)
C104H198O21 1784.672 Download ChemDraw structure file





Thermoproteus tenax(Ref. 0145)




293
b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyldiglycerol tetraether(Ref. 0145) / b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyl caldarchaeol
EEL1045
Toshihiro Itoh
GL-4(Ref. 0145)
C104H198O21 1784.672 Download ChemDraw structure file





Thermoproteus tenax(Ref. 0145)




294
b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyldiglycerol tetraether(Ref. 0145) / b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyl caldarchaeol
EEL1046
Toshihiro Itoh
GL-4(Ref. 0145)
C104H196O21 1782.656 Download ChemDraw structure file





Thermoproteus tenax(Ref. 0145)




295
b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyldiglycerol tetraether(Ref. 0145) / b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyl-(1,6)-b-D-glucopyranosyl caldarchaeol
EEL1047
Toshihiro Itoh
GL-4(Ref. 0145)
C104H194O21 1780.641 Download ChemDraw structure file





Thermoproteus tenax(Ref. 0145)




296
b-D-glucopyranosyl-caldarchaetidyl -myo-inositol(Ref. 0145)
EEL1048
Toshihiro Itoh
PL-3(Ref. 0145)
C98H191O19P 1704.528 Download ChemDraw structure file





Thermoproteus tenax(Ref. 0145)/Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




297
b-D-glucopyranosyl-caldarchaetidyl -myo-inositol(Ref. 0145)
EEL1049
Toshihiro Itoh
PL-3(Ref. 0145)
C98H189O19P 1702.512 Download ChemDraw structure file





Thermoproteus tenax(Ref. 0145)




298
b-D-glucopyranosyl-caldarchaetidyl -myo-inositol(Ref. 0145)
EEL1050
Toshihiro Itoh
PL-3(Ref. 0145)
C98H189O19P 1702.512 Download ChemDraw structure file





Thermoproteus tenax(Ref. 0145)/Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




299
b-D-glucopyranosyl-caldarchaetidyl -myo-inositol(Ref. 0145)
EEL1051
Toshihiro Itoh
PL-3(Ref. 0145)
C98H187O19P 1700.496 Download ChemDraw structure file





Thermoproteus tenax(Ref. 0145)/Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




300
b-D-glucopyranosyl-caldarchaetidyl -myo-inositol(Ref. 0145)
EEL1052
Toshihiro Itoh
PL-3(Ref. 0145)
C98H185O19P 1698.480 Download ChemDraw structure file





Thermoproteus tenax(Ref. 0145)/Pyrobaculum islandicum, Pyrobaculum organotrophucum(Ref. 0159)




301
1-O-decylglycerol(Ref. 0040)
EEL2001
Keizo Waku
10:0-Gro monoether
C13H28O3 232.360

38.5degC



TLC, THF-H2O (1:1) Rf 0.86





302
1-O-dodecylglycerol(Ref. 0040)
EEL2002
Keizo Waku
12:0-Gro monoether
C15H32O3 260.413

49.5degC



TLC, THF-H2O (1:1) Rf 0.70





303
1-O-tetradecylglycerol(Ref. 0040)
EEL2003
Keizo Waku
14:0-Gro monoether
C17H36O3 288.466

58.5degC



TLC, THF-H2O (1:1) Rf 0.55





304
1-O-(cis,cis-9,12-octadecadienyl)glycerol(Ref. 0040)
EEL2005
Keizo Waku
18:2-Gro monoether
C21H40O3 340.541

8degC



TLC, THF-H2O (1:1) Rf 0.49





305
1-O-(cis,cis,cis-9,12,15-octadecatrienyl)glycerol(Ref. 0040)
EEL2006
Keizo Waku
18:3-Gro monoether
C21H38O3 338.525

13degC



TLC, THF-H2O (1:1) Rf 0.58





306
1,2-dihexadecylglycerol/dipalmitylglycerol
1,2-di-O-hexadecyl-sn-glycerol(Ref. 0041)
EEL2007
Keizo Waku
di-16:0-Gro diether
C35H72O3 540.944
synthesized by alkylation of L-a-O-benzyl glycerol with hexadecyl bromide and potassium hydroxide in boiling benzene, followed by removal of the benzyl group by hydrogenolysis with palladium catalyst.
48.5-49.5degC
[a]D = -7.5deg, [M]D = -41deg




synthetic compound
synthesized by alkylation of L-a-O-benzyl glycerol with hexadecyl bromide and potassium hydroxide in boiling benzene, followed by removal of the benzyl group by hydrogenolysis with palladium catalyst.



307
1,2-di-O-octadecylglycerol (Ref. 0041)
EEL2008
Keizo Waku
di-18:0-Gro diether
C39H80O3 597.051
synthesized by alkylation of L-a-O-benzyl glycerol with octadecyl bromide and potassium hydroxide in boiling benzene, followed by removal of the benzyl group by hydrogenolysis with palladium catalyst.
53.5-54.5degC
[a]D = -6.9deg, [M]D = -41deg




synthetic compound
synthesized by alkylation of L-a-O-benzyl glycerol with octadecyl bromide and potassium hydroxide in boiling benzene, followed by removal of the benzyl group by hydrogenolysis with palladium catalyst.



308
1-O-octadecyl-2-O-(cis-9-octadecenyl)glycerol(Ref. 0043)
EEL2009
Keizo Waku
18:0, 18:1-Gro diether
C39H78O3 595.035

23-24degC









309
1,2,3-tri-O-octyl-sn-glycerol(Ref. 0044)
EEL2010
Keizo Waku
tri-8:0-Gro triether
C27H56O3 428.732










310
1-O-dodecyl-2,3-di-O-decylglycerol(Ref. 0045/0046)
EEL2011
Keizo Waku
12:0, di-10:0-Gro triether
C35H72O3 540.944

-5degC









311
1,2,3-tri-O-hexadecyl-sn-glycerol(Ref. 0043)
EEL2012
Keizo Waku
tri-16:0-Gro triether
C51H104O3 765.370

47-48degC









312
1,2,3-tri-O-octadecyl-sn-glycerol(Ref. 0043)
EEL2013
Keizo Waku
tri-18:0-Gro triether
C57H116O3 849.529

57.5-58degC









313
1,2,3-tri-O-(cis-9-octadecenyl)-sn-glycerol(Ref. 0043)
EEL2014
Keizo Waku
tri-18:1-Gro triether
C57H110O3 843.482

-11degC









314
2-O-cis-9'-octadecenylglycerol(Ref. 0047)
EEL2015
Keizo Waku
18:1-Gro monoether
C21H42O3 342.556


GC-MS spectra C4-C7 monounsaturations at m/e 55,69,83,97







315
1-palmitylglycerophosphate
1-O-hexadecyl-sn-glycerol-3-phosphate(Ref. 0048)
EEL2016
Keizo Waku
C16:0-GP/1Hx-GPA
C19H41O6P 396.499
Prepared by hydrolysis of 1-O-HEXADECYL-GPC with phospholipase D




synthetic product
Prepared by hydrolysis of 1-O-HEXADECYL-GPC with phospholipase D



316
Lyso PAF
1-O-hexadecyl-sn-glycerophosphocholine(Ref. 0048)
EEL2017
Keizo Waku
C16:0-GPC/1Hx-GPC
C24H52O6PN 481.647
prepared by hydrolysis of 1(3)Hx-2Ac-GPC (racemic compound) with phospholipase A2




known as the PAF precursor
prepared by hydrolysis of 1(3)Hx-2Ac-GPC (racemic compound) with phospholipase A2



317
1,2-di-O-cis-9'-octadecenyl-sn-glycero-3-phosphocholine(Ref. 0049)
EEL2018
Keizo Waku
C44H88O6PN 758.146

214-216degC
[a]D = +1.4deg (34mg/ml CHCl3:MeOH 1:1)









318
1-O-cis-9'-octadecenyl-3-O-octadecanoyl-sn-glycero-2-phosphoethanolamine(Ref. 0049)
EEL2019
Keizo Waku
C41H84O6PN 718.083 Download ChemDraw structure file

192degC
[a]d-22=-3.5 (28mg/ml CHCl3:MeOH 1:1)









319
1-O-cis-9'-octadecenyl-3-O-octadecanoyl-sn-glycero-2-phosphcholine(Ref. 0049)
EEL2020
Keizo Waku
C44H90O6PN 760.162 Download ChemDraw structure file

225-226degC
[a]d-22=-3.8
cis double bond(300cm-1), -CH3,-CH2(2920,2850,1460,1370cm-1), ester C=O(1730cm-1), ether -C-O-C(1110cm-1 as a shoulder), P-O-C(950cm-1),P-O(-)(1070cm-1)P=O(1230cm-1), -OH(H2O)(3330cm-1)









320
1-undecylglycerol(racemic compound)(Ref. 0050)
EEL2021
Keizo Waku
C11:0-Gro monoether
C14H30O3 246.386

37degC (Ref. 0050)
CST(critical solution temperature with nitromethane) 61.5degC(Ref. 0050)




synthetic product (racemic compound)




321
1-tridecylglycerol(racemic compound)(Ref. 0050)
EEL2022
Keizo Waku
C13:0-Gro monoether
C16H34O3 274.439

47.5degC (Ref. 0050)
CST=70.5degC(Ref. 0050)




synthetic product (racemic compound)




322
1-pentadecylglycerol(racemic compound)(Ref. 0050)
EEL2023
Keizo Waku
C15:0-Gro monoether
C18H38O3 302.493

CST=77.5degC(Ref. 0050)




synthetic product (racemic compound)




323
1-anteiso pentadecylglycerol
1-(12'-methyltetradecyl)glycerol(racemic compound)(Ref. 0051)