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Lipopolysaccharide

(total 734)
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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
2'N-3''(tetradecanoyloxy)tetradecanoyl, 3'-O-3''hydroxytetradecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxytetradecanoyl,3-O-3''hydroxydecanoyl D-glucosamine 1,4'-bisphosphate
CLS0101
Yoshio Kumazawa
C78H146O24N2P2 1557.940 Download ChemDraw structure file
B. pertussis endotoxin is inducer of interleukin-1 secretion in human monocytes(Ref. 0103)

252Cf PDM
[Spectrum 0001] 252Cf PDM
[Spectrum 0002] Positive ion FAB/MS
[Spectrum 0003]

Thin-layer chromatography
[Chromatogram 0001]
Bordetella pertussis 1414(Ref. 0101)




2
b-D-Qui3NAc-(1a_right2)-b-D-Qui3NAc
2'N-3''(tetradecanoyloxy)tetradecanoyl, 3'-O-3''hydroxytetradecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxytetradecanoyl,3-O-3''hydroxydodecanoyl D-glucosamine 1,4'-bisphosphate
CLS0102
Yoshio Kumazawa
C80H152O24N2P2 1588.009 Download ChemDraw structure file
toxicity

Positive-ion PDM
[Spectrum 0004] Negative-ion PDM
[Spectrum 0005]


Bordetella bronchiseptica(Ref. 0102)




3 No image
CLS0211
Yoshio Kumazawa
b-D-Qui3NAc-(1a_right2)-b-D-Qui3NAc

1H NMR chemical shift for O:30 C1
[Table 0001]
Positive ion FAB/MS(O:30 C1)
[Spectrum 0006]
Positive ion FAB/MS(O:30 C2 and O:30 C3)
[Spectrum 0007]
EI/MS of alditol acetate derivative
[Spectrum 0008]


Campylobactor coli Serotype O:30(Ref. 0211)




4
2'N-3""(hexadecanoyloxy)tetradecanoyl,3'N-3""(hexadecanoyloxy)tetradecanoyl, 2',3'-dideoxy b-(1a_right6) D-glucosyl 2N-3""hydroxytetradecanoyl,3-O-3""hydroxytetradecanoyl D-glucosamine 1,4'-bisphosphate
CLS0212
Yoshio Kumazawa
C100H189O24N3P2 1879.524 Download ChemDraw structure file
Induce toxic lethality in galactosamine-sensitized mice
[Table 0002]
Pyrogenicity in rabbits
Tumor necrosis factor (TNF) secretion from mouse peritoneal macrophages
[Table 0003]
Inhibition of passive haemolysis
[Table 0004]

Laser desorption mass spectra of dephoshorylated free lipid A
[Spectrum 0009]
EI/MS of permethylated and N-acetylated disaccharides derivatives
[Spectrum 0010]


Campylobactor jejuni(Ref. 0212/0213)



Chemical composition of LPS of C. jejuni strains
[Table 0005]
Stractural analysis of the lipid A component of Campylobactor jejuni CCUG 10936 (serotype O:2)(Ref. 0213)
5
2'N-3''(nonadecanoyloxy)eicosanoyl, 3'-O-pentadecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxytetradecanoyl,3-O-3''hydroxyeicosanoyl D-glucosamine 4'-phosphate
CLS0221
Yoshio Kumazawa
C100H190O19N2P 1755.554 Download ChemDraw structure file
Chlamydial LPS was less potent than Enterobacteriaceae LPS, as defined by its ability to activate mononuclear phagocytes and a Chinese hamster ovary cell line trancefected with the putative LPS receptor CD14(Ref. 0222)

Positive-ion MALDI/TOF MS MALDI/IT MS, and LSIMS spectra
[Spectrum 0011]
High-energy CID spectrum of a quasi-molecular ion (MNa+) at 1794 atomic mass units
[Spectrum 0012]

Reverse-phase HPLC of the dimethyl-monophosphoryl lipid A
[Chromatogram 0002]
Chlamydia trachomatis(Ref. 0221)



Proposed fatty acyl distribution of dimethyl-monophosphoryl lipid A components
[Table 0006]
6 No image
2'-amino-1',3'-dihydroxypropane-3'-p-6-D-Glcp(a1-3)radyl2Gro
CLS0231
Yoshio Kumazawa




Two dimensional TLC of the polar lipids
[Chromatogram 0003]
Clostridium innocuum(Ref. 0231)



Apolar chain compositions of the total lipids and glycolipids I and II
[Table 0007]
Membrane polar lipid composition
[Table 0008]
Comparison of lipid amphiphile composition of Clostridium innocuum and Acholeplasma laidlawii
[Table 0009]
7
2'N-3''(dodecanoyloxy)decanoyl, 3'-O-3''hydroxydecanoyl b-(1a_right6) D-glucosaminyl 2N-3''(tetradecanoyloxy)decanoyl,3-O-3''hydroxydecanoyl D-glucosamine 1,4'-bisphosphate
CLS0241
Yoshio Kumazawa
C78H144O25N2P2 1571.924 Download ChemDraw structure file

600MHz NMR spectra of phosphoryl-methylated lipid A
[Spectrum 0016]
[Table 0011]
EI-MS and fragmentation pattern of fatty acids methyl esters
[Spectrum 0013]
LSI-MS of de-O-acylated lipid A
[Spectrum 0014]
ESI-MS in negative mode of intact lipid A
[Spectrum 0015]


Comamonas testosteroni(Ref. 0241)



Chemical composition of lipid A
[Table 0010]
8
2'N-3''(dodecanoyloxy)tetradecanoyl, 3'-O-3''(hydroxytetradecanoyloxy)tetradecanoyl b-(1a_right6) D-glucosaminyl 2N-3''(hexadecanoyloxy)tetradecanoyl,3-O-3''hydroxytetradecanoyl D-glucosamine 4'-phosphate
CLS0411
Yoshio Kumazawa
C110H206O23N2P 1955.786 Download ChemDraw structure file
Eliminating the pulmonary toxicity(Ref. 0411)

Interpretation of negative-ion ES mass spectra of lipid A
[Table 0012]
Lower mass region of the negative-ion ES mass spectrum of lipid A
[Spectrum 0017]
Negative-ion ES mass spectra of lipid A obtained for LPS hydrosis
[Spectrum 0018]


Enterobacter agglomerans(Ref. 0411)




9
2N-3''hydroxytetradecanoyl, 3-O-3''hydroxytetradecanoyl D-glucosamine 1-phosphate
CLS0421
Yoshio Kumazawa
C34H66O12NP 711.861 Download ChemDraw structure file
No stimulation of lymphocytes from C3H/HeJ mice
Polymyxin B abrogates lymphocyte stimulation
Induction the proliferation and maturation of lymphocytes to antibody-producing plaque-forming cells(Ref. 0421)




Escherichia coli(Ref. 0421)



Postulated structure of lipid A based on the discovery of lipid X
[Table 0013]
10
2'N-3''(dodecanoyloxy)tetradecanoyl, 3'-O-3''(tetradecanoyloxy)tetradecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxytetradecanoyl,3-O-3''hydroxytetradecanoyl D-glucosamine 1,4'-bisphosphate
CLS0422
Yoshio Kumazawa
C94H176O25N2P2 1796.349 Download ChemDraw structure file

1H-1H shift correlation spectrum at 500 MHz of HPLC-purified hexamethyl hexaacyl Re-LPS
[Spectrum 0019]
Proton NMR spectrum of the HPLC-purified hexamethyl hexaacyl Re-LPS
[Spectrum 0021]
13C and 13C-DEPT spectra
[Spectrum 0022]
Partial PD mass spectrum of HPLC-purified hexamethyl hexaacyl Re-LPS
[Spectrum 0020]

Reverse-phase HPLC of hexamethyl Re-LPS
[Chromatogram 0004]
Gel permeation chromatography of hexamethyl Re-LPS
[Chromatogram 0005]
Escherichia coli D31m4(Ref. 0422)



Quantitation of the phosphorus content of the HPLC-purified methylated Re-LPS
[Table 0014]
11
2'N-3''(dodecanoyloxy)tetradecanoyl, 3'-O-3''(tetradecanoyloxy)tetradecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxytetradecanoyl,3-O-3''hydroxytetradecanoyl D-glucosamine 1,4'-bisphosphate
CLS0423
Yoshio Kumazawa
bisphosphorylated disaccharide b-D-GlcpN-4-P-(1a_right6)-a-D-GlcpN-1-P
C94H176O25N2P2 1796.349 Download ChemDraw structure file
Antibody obtained after immunization with the J-5 mutant of Escherichia coli O111 was suited to induce cross-reactive lipid A(Ref. 0425)
13C-NMR spectrum of the hydrophilic backbone from lipid A
[Spectrum 0023]
1H,1H-COSY-NMR spectrum of the hydrophilic backbone from lipid A
[Spectrum 0024]
1H,13C-COSY-NMR spectrum of the hydrophilic backbone from lipid A
[Spectrum 0025]
Laser-desorption mass spectrum of dephosphorylated lipid A
[Spectrum 0026]


Escherichia coli J-5(Ref. 0423)



1H-NMR data
[Table 0015]
13C-NMR data
[Table 0016]
12
2'N-3''(dodecanoyloxy)tetradecanoyl, 3'-O-3''(tetradecanoyloxy)tetradecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxytetradecanoyl,3-O-3''hydroxytetradecanoyl D-glucosamine 1,4'-bisphosphate
CLS0424
Yoshio Kumazawa
C94H176O25N2P2 1796.349 Download ChemDraw structure file
Folding of PhoE protein
[Tables 0017/0018]
LPS-dependent protein folding
[Chromatograms 0006/0007/0008]




Escherichia coli J-5(Ref. 0424)




13
2'N-3''(pentadecanoyloxy)heptadecanoyl, 3'-O-3''hydroxyhexadecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxyheptadecanoyl,3-O-3''hydroxypentadecanoyl D-glucosamine 1-phosphate
CLS0511
Yoshio Kumazawa
C92H174O21N2P 1675.341 Download ChemDraw structure file
low toxicity or non-toxic(Ref. 0511)
1H NMR data for the peracetylated derivative
[Table 0019]
13C NMR data for the peracetylated derivative
[Table 0020]
1H NMR data for phosphoryl-methylated lipid A
[Table 0021]
EI-mass spectrum of methyl ester derivatives of (R)-3-O-(13-methyltetradecanoyl)-15-methylhexadecanoic acid
[Spectrum 0027]
LSI-mass spectrum of de-O-acylated lipid A in the negative-ion mode
[Spectrum 0028]


Flavobacterium meningosepticum IFO12535(Ref. 0511)




14
2'N-3''(tetradecanoyloxy)tetradecanoyl, 3'-O-3''(tetradecanoyloxy)tetradecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxytetradecanoyl,3-O-3''hydroxytetradecanoyl D-glucosamine 1,4'-bisphosphate
CLS0611
Yoshio Kumazawa
dOclApa(2""-6')GlcNpb6GlcNpaP
C96H180O25N2P2 1824.402 Download ChemDraw structure file


Laser desorption mass spectrum of dephosphorylated free lipid A
[Spectrum 0029]
EI mass spectra of permethylated dOclA 4-phosphate and dOclA 5-phosphate
[Spectrum 0030]

SDS/PAGE
[Chromatogram 0009]
Gas-liquid chromatogram of dOclA phosphate derivatives
[Chromatogram 0010]
Haemophilus influenzae strain I-69(Ref. 0611)



Chemical composition
[Table 0022]
15
2'N-3''(octadecanoyloxy)octadecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxyoctadecanoyl D-glucosamine 1-(2-aminoethyl)phosphate
CLS0711
Yoshio Kumazawa
C68H132O17N3P 1294.759 Download ChemDraw structure file

1H-1H COSY and 1H-1H TOCSY spectra of purified lipid A
[Spectrum 0031]
ESI-MS/MS and LSIMS/MS spectra of the purified lipid A
[Spectrum 0032]


Helicobacter pylori strain 206-1(Ref. 0711)




16
2'N-3''(octadecanoyloxy)octadecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxyoctadecanoyl,3-O-3''hydroxyhexadecanoyl D-glucosamine 1-phosphate
CLS0712
Yoshio Kumazawa
C82H156O19N2P 1505.092 Download ChemDraw structure file
Avoid or minimize the host defence(Ref. 0713)
Low pyrogenicity and toxicity
31P-NMR spectrum of free lipid A
[Spectrum 0083]
EI mass spectrum of the permethylated and N-acetylated disaccharide derived from free lipid A
[Spectrum 0082]
Positive-ion LD mass spectra of free dephosphorylated lipid A
[Spectrum 0084]
Assaignment of peaks in the LD mass spectrum of free dephosphorylated lipid A
[Tables 0026/0027]


Helicobacter pylori(Ref. 0712)



Chemical composition of lipid A
[Table 0023]
Identity of methylated sugars
[Table 0024]
Nature and amount of fatty acid methyl esters released from free lipid A
[Table 0025]
Fragmentation patterns of permethylated and N-acylated glucosamine derivatives
[Spectrum 0085]
17
2'N-3''(tetradecanoyloxy)tetradecanoyl, 3'-O-tetradecanoyl b-(1a_right6) D-glucosaminyl 2N-3''(tetradecanoyloxy)tetradecanoyl, 3-O-tetradecanoyl D-glucosamine 1-di ,4'-phosphate
CLS1011
Yoshio Kumazawa
C96H181O28N2P3 1904.382 Download ChemDraw structure file
Activation of the complement system(Ref. 1011)
Aggregation size
[Table 0028]
Activation of the classical pathway and the alternative pathway
[Table 0029]
Functional CP activation
[Table 0030]
Complement consumption by different preparations of LPS
[Table 0031]




Klebsiella pneumoniae I-145(Ref. 1011)




18
2'N-3''(dodecanoyloxy)tetradecanoyl, 3'-O-3''hydroxydodecanoyl b-(1a_right6) D-glucosaminyl 2N-3''(dodecanoyloxy)tetradecanoyl, 3-O-3''hydroxydodecanoyl D-glucosamine 4'-phosphate
CLS1311
Yoshio Kumazawa
C88H164O22N2P 1633.218 Download ChemDraw structure file


HPLC of MLA fraction I, and LD-mass spectra
[Spectrum 0033]
FAB-mass spectrum of HPLC peak 1-3 from MLA fraction I
[Spectrum 0034]

Analytical TLC of silicic acid column purified MLA fractions
[Chromatogram 0011]
Neisseria gonorrhoeae(Ref. 1311)



Fatty acid distribution of HPLC-fractionated dimethyl MLA, fraction I
[Table 0032]
Fatty acid distribution of the major MLA components obtained from the LPS
[Table 0034]
19
2'N-3''(dodecanoyloxy)tetradecanoyl, 3'-O-3''hydroxydodecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxytetradecanoyl, 3-O-3''hydroxydodecanoyl D-glucosamine 4'-phosphate
CLS1313
Yoshio Kumazawa
C76H142O21N2P 1450.915 Download ChemDraw structure file


HPLC of MLA fraction II, and LD-mass spectra
[Spectrum 0035]
FAB-mass spectrum of HPLC peak 1-3 from MLA fraction II
[Spectra 0036]

Analytical TLC of silicic acid column purified MLA fractions
[Chromatogram 0011]
Neisseria gonorrhoeae(Ref. 1311)



Fatty acid distribution of HPLC-fractionated dimethyl MLA, fraction I
[Table 0033]
Fatty acid distribution of the major MLA components obtained from the LPS
[Table 0034]
20
2'N-3''(undecanoyloxy)tridecanoyl, 3'-O-3''(undecanoyloxy)tridodecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxytridecanoyl, 3-O-3''hydroxytridecanoyl D-glucosamine 1-phosphate, 4'-4''-amino-4-deoxyarabinose-phosphate
CLS1411
Yoshio Kumazawa
C97H181O28N3P2 1899.426 Download ChemDraw structure file
Susceptibility of P. cerevisiiphilus
[Table 0037]
31P-NMR spectra of de-O-acylated lipopolysaccharide
[Spectrum 0037]
Positive ion LD-MS of free dephosphorylated lipid A
[Spectrum 0038]
Assignment of peaks in the LD mass spectra of free dephosphorylated lipid A
[Table 0036]
Interpretation of the fragmentation pattern of free dephosphorylated lipid A
[Spectrum 0039]


Pectinatus cerevisiiphilus and Pectinatus frisingensis(Ref. 1411)



Partial chemical composition of P. cerevisiiphilus lipopolysaccharide and subsequent degradation products
[Table 0035]
21
2'N-3''(dodecanoyloxy)tetradecanoyl, 3'-O-3''(tetradecanoyloxy)tetradecanoyl b-(1a_right6) D-glucosaminyl 2N-3''(hexadecanoyloxy)tetradecanoyl, 3-O-3''hydroxytetradecanoyl D-glucosamine 4'-phosphate
CLS1511
Yoshio Kumazawa
C110H206O26N2P2 2034.758 Download ChemDraw structure file
The E. coli type heptaacyl lipid A from P. agglomerans showed the highest activity including endogenous TNF induction(Ref. 1512)
NMR spectral data
[Table 0039]
Positive FAB mass spectrum
[Spectrum 0040]
Summary of mass peaks observed in the positive FAB mass
[Table 0040]

Gas chromatograms of acyl residues liberated from P. agglomerans lipid A
[Chromatogram 0012]
Pantoea agglomerans(Ref. 1511>



Chemical composition of purified lipid A
[Table 0038]
22
2'N-3''(13-methyltetradecanoyloxy)-15''-methylhexadecanoyl, 3'-O-3''hydroxyhexadecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxyhexadecanoyl, 3-O-3''hydroxypentadecanoyl D-glucosamine 1-phosphate
CLS1521
Yoshio Kumazawa
C91H168O21N2P 1657.282 Download ChemDraw structure file


Laser desorption mass spectra of B. fragilis free lipid A
[Spectrum 0041]


Bacteroides fragilis NCTC 9343



Time dependence of phosphate release and appearance of reducing glucosamine
[Table 0041]
Chemical composition of Bacteroides fragilis NCTC 934 lipopolysaccharide
[Table 0042]
Fatty acid composition of B. fragilis lipopolysaccharide
[Table 0043]
Interpretation of the pseudomolecular ion at m/z=1715 (M+Cs)+ obtained with acid-treated B. fragilis lipid A
[Table 0044]
23
2'N-3''(hexadecanoyloxy)-15''-methylhexadecanoyl, 3'-O-3''hydroxy-13""-methyltetradecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxy-15""-methylhexadecanoyl, 3-O-3''hydroxyhexadecanoyl D-glucosamine 1-phosphate
CLS1522
Yoshio Kumazawa
C93H176O21N2P 1689.367 Download ChemDraw structure file
Bone resorption activity and induction of various inflammatory cytokines in human gingival fibroblast cultures(Ref. 1524)
Stimulation of the splenocytes of endotoxin-nonresponsive C3H/HeJ mice to undergo mitosis(Ref. 1525)
31P NMR spectrum of P. gingivalis de-O-acylated lipid A
[Spectrum 0045]
PH-HMQC NMR spectrum of P. gingivalis phosphoryl-methylated lipid A
[Spectrum 0045]
EI-mass spectrum and fragmentation pattern of (R)-3-O-(hexadecanoyl)-15-methylhexadecanoic acid methyl ester
[Spectrum 0042]
LSI-mass spectrum of P. gingivalis native lipid A in negative-ion mode
[Spectrum 0043]
[Table 0045]
FAB-MS/MS of P. gingivalis native lipid A in negative-ion mode
[Spectrum 0044]


Porphyromonas gingivalis(Ref. 1522)




24
2'N-3''(hexadecanoyloxy)-15''-methylhexadecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxy-15""-methylhexadecanoyl D-glucosamine 1-phosphate
CLS1523
Yoshio Kumazawa
C62H118O17N2P 1194.577 Download ChemDraw structure file
Stimulation of the splenocytes from C3H/HeN and C3H/HeJ mice(Ref. 1523)
Low endotoxic properties(Ref. 1526)
Counter plot of the 2D COSY spectrum of the peracetate of dephosphorylated lipid A
[Spectrum 0046]
Negative ion FAB-MS-MS spectrum of P. gingivalis lipid A
[Spectrum 0047]


Porphyromonas (Bacteroides) gingivalis strain 381(Ref. 1523)




25 No image
2,3-diamino-2,3-dideoxy-D-glucose
CLS1532
Yoshio Kumazawa
Endotoxic activities of LPS and free lipid A
[Table 0046]
endotoxic activities including lethal toxicity, pyrogenicity, local Shwartzman activity, body weight-decreasing toxicity and Limulus activity(Ref. 1532)
31P NMR spectra of lipid A and LPS
[Spectrum 0048]


TLC of free lipid A
[Chromatogram 0013]
Pseudomonas diminuta



Chemical composition of LPS and lipid A
[Table 0047]
26 No image
2,3-diamino-2,3-dideoxy-D-glucose
CLS1533
Yoshio Kumazawa
Stronger TNF-inducing activity
[Table 0049]



Thin-layer chromatogram of purified lipid A
[Chromatogram 0014]
Pseudomonas diminuta and Pseudomonas vesicularis(Ref. 1533)



Chemical composition of purified lipid A
[Table 0048]
27
a-(1a_right4) galacturonyl 2'N-3''hydroxytetradecanoyl,3'-O-3''hydroxytetradecanoyl b-(1a_right6) D-glucosaminyl 1-O-27''hydroxyoctacosanoyl 2N-3''hydroxytetradecanoyl,3,4-O-bishydroxytetradecanoyl D-glucosamine-onate
CLS1711
Yoshio Kumazawa
Download ChemDraw structure file

A proton spectrum showing the anomeric region of the N-acetylated hydrazinolysis product of R. leguminosarum lipid A
[Spectrum 0050]
Mass spectra (CI and EI) of the TMS methyl ester of 2-aminogluconic acid
[Spectrum 0049]
Mass spectra of the N-acylglucosamine methyl glycoside released from R. leguminosarum bv. phaseoli lipid A
[Spectrum 0051]
Mass spectra of partially methylated alditol acetates
[Spectrum 0052]
Mass spectra (EI and CI) of the acyloxyacyl residue
[Spectrum 0053]
Complete positive ion electrospray mass spectrum of the R. leguminosarum bv. phaseoli de-O-acyl lipid A
[Spectrum 0054]
FAB-MS spectra of the de-O-acylated lipid A
[Spectrum 0055]Complete positive ion LSI-MS spectrum of the de-O-acyl lipid A
[Spectrum 0056]

Total ion chromatograms of the fatty acids derived from R. leguminosaram bv. phaseoli CE3 lipid A
[Chromatogram 0015]
Total ion chromatogram showing the carbohydrate and fatty acid composition of the de-O-acylated lipid A
[Chromatogram 0016]
Rhizobium leguminosarum bv. phaseoli(Ref. 1711)



Chemical composition of R. leguminosarum bv.phaseoli CE3 lipid A
[Table 0050]
Relative recovery of ester- and amide-linked fatty acids during de-O-acylation of lipid A
[Table 0051]
Ions derived from electrospray mass spectrometry of the de-O-acyl lipid A
[Table 0052]
A special carrier protein for transferring long hydroxylated fatty acids(Ref. 1712)
28
27-hydroxyoctacosanoic acid (a major structural fatty acyl component of LPS)
CLS1721
Yoshio Kumazawa
C28H56O3 440.742 Download ChemDraw structure file

250 MHz-Proton NMR spectrum of the crude LPS of R. trifolli ANU 843
[Spectrum 0057]
Proton NMR spectrum of the purified lipid fragment
[Spectrum 0058]
Proton NMR spectrum of phenylcarbamate derivative of purified lipid A
[Spectrum 0059]
Proton NMR spectrum of the acetylated fatty acid methyl ester
[Spectrum 0060]
Proton NMR spectrum of 1,27-diacetoxyoctacosane
[Spectrum 0062]
Electron impact mass spectrum of the acetylated methyl ester of 27-hydroxyoctacosanoic acid
[Spectrum 0061]
Electron impact mass spectrum of diol diacetate
[Spectrum 0063]


Rhizobium trifolii ANU 843(Ref. 1721)



a major structural fatty acyl component of LPS of R. trifolli ANU 843(Ref. 1721)
29
2N-27'hydroxyoctacosanoyl, 3-O-3'hydroxytetradecanoyl D-glucosamine
CLS1722
Yoshio Kumazawa
C48H93O9N 828.253 Download ChemDraw structure file

250 MHz 1H NMR spectrum of the methanol fraction from C18 reverse-phase chromatography of crude lipid A
[Spectrum 0065]
13C NMR spectrum of the methanol fraction from C18 reverse-phase chromatography
[Spectrum 0066]
250 MHz 1H NMR spectrum of the faster migrating band on preparative TLC analysis of lipid A
[Spectrum 0067]
1H NMR spectrum of the slower migrating band obtained by preparative TLC analysis of lipid A
[Spectrum 0069]
FAB-MS spectrum of the slower migrating TLC band
[Spectrum 0064]
FAB-MS spectrum of the faster migrating band
[Spectrum 0068]


Rhizobium trifolii ANU843(Ref. 1722)




30 No image
2'N-3''(tetradecenoyloxy)tetradecanoyl, 3'-O-3''hydroxydecanoyl b-(1a_right6) D-glucosaminyl 2N-3''ketotetradecanoyl, 3-O-3''hydroxydecanoyl D-glucosamine 1,4'-bisphosphate
CLS1731
Yoshio Kumazawa
C74H136O24N2P2 1499.818
Taxol-induced mitotic arrest
[Table 0053]
LPS inhibitors block taxol-induced gene expression in murine macrophages
[Chromatogram 0018]
LPS inhibitors block taxol-induced TNF secretion in murine macrophages
[Table 0054]
Raising the concentration of taxol overrides RsDPLA inhibition of TNF-a mRNA
[Table 0055]
LPS inhibitors block taxol-induced protein-tyrosine phosphorylation
[Chromatogram 0019]
Stimulation of murine macrophages to express low levels of TNF-a m RNA and bioactivity
[Chromatogram 0020]
Macrophage genes induced by RsDPLA
[Table 0056]
Effects of high concentration of SDZ 880.431 on LPS- and HKSA-induced gene expression
[Table 0057]
RsDPLA and SDZ 880.431 inhibit LPS- but not HKSA-induced TNF secretion
[Table 0058]
Inhibition of LPS-induced gene expression by RsDPLA and SDZ 880.431
[Table 0059]
Effect of serum-free conditions on bidirectional effects of SDZ 880.431
[Table 0060]
Effect of sample dilution on bidirectional effects of SDZ880.431
[Table 0061]
Inhibition of LPS-induced gene expression by RsDPLA and SDZ 880.431
[Chromatogram 0021]
Bidirectional effects on TNF-a and IP-10 expression by the combination of high concentrations of LPS and RsDPLA or SDZ 880.431
[Chromatogram 0022]

LSIMS, MALDI/IT MS, and MALDI/TOF MS positive ion spectra of R. sphaeroides DPLA
[Spectrum 0070]
High-energy CID spectra of carboxylate anions at m/z 187
[Spectrum 0071]
LSIMS negative ion spectrum of R. sphaeroides DPLA
[Spectrum 0072]
High-energy CID spectrum of [M+Na]+
[Spectrum 0073]
Low-energy CID spectrum of oxonium ion B1+
[Spectrum 0074]
High-energy CID spectrum of a carboxylate anion at m/z 22+5
[Spectrum 0075]

Fractionation of tetramethyl DPLA from R. sphaeroides by reversed-phase HPLC
[Chromatogram 0017]
Rhodobacter sphaeroides(Ref. 1731/1732/1733)




31
2'N-3''(dodecanoyloxy)tetradecanoyl, 3'-O-3''(tetradecanoyloxy)tetradecanoyl b-(1a_right6) D-glucosaminyl 2N-3''(hexadecanoyloxy)tetradecanoyl, 3-O-3''hydroxytetradecanoyl D-glucosamine 1,4'-bisphosphate
CLS1811
Yoshio Kumazawa
C110H206O26N2P2 2034.758 Download ChemDraw structure file





Salmonella minnesota(Ref. 1811)



Melting enthalpies of ice-water endotherm
[Table 0062]
Peak position of the symmetric stretching vibration of the methylene groups ns(CH2) versus temperature
[Table 0063]
X-ray diffraction patterns of LPS Rd2 preparations at a water concentration of 70% between 5 and 60degC
[Table 0064]
X-ray diffraction patterns at 40degC and [LPS]:[Mg2+]>>1 versus water content for LPS Rd1(P+) and LPS Rb
[Table 0065]
Deconvoluted X-ray diffraction spectra for LPS Rd2 in 70% distilled water at 20 and 40degC
[Table 0066]
X-ray diffraction patterns at 40degC and 55% water content without Mg2+
[Table 0067]
X-ray diffraction patterns between 20 and 60degC at 70% water content and [LPS]:[Mg2+]=3:1 M
[Table 0068]
Lamellar periodicities d1 of free lipid A and various rough mutant LPS
[Table 0069](Ref. 1811)
32
2'N-3''(dodecanoyloxy)tetradecanoyl, 3'-O-3''(tetradecanoyloxy)tetradecanoyl b-(1a_right6) D-glucosaminyl 2N-3''(hexadecanoyloxy)tetradecanoyl, 3-O-3''hydroxytetradecanoyl D-glucosamine 1,4'-bisphosphate
CLS1813
Yoshio Kumazawa
C108H202O26N2P2 2006.705 Download ChemDraw structure file





Salmonella minesota, Escherichia coli(Ref. 1813)



Band contour analysis of the >C=O ester stretching bands
[Table 0070]
Representative X-ray scattering pattern of synthetic and bacterial lipid A and partial structures
[Table 0071]
Compilation of X-ray and Fourier-transform-infrared data on lipid A, partial structures and analogues of lipid A
[Table 0072]
33
2'N-3''(dodecanoyloxy)tetradecanoyl, 3'-O-3''(tetradecanoyloxy)tetradecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxytetradecanoyl, 3-O-3''hydroxytetradecanoyl D-glucosamine 4'-phosphate
CLS1821
Yoshio Kumazawa
C94H176O22N2P 1717.377 Download ChemDraw structure file

Proton NMR spectrum of the dimethyl pentatrimethylsilyl monophosphoryl lipid A
[Spectrum 0076]
Resolution enhanced spectrum of the dimethyl pentatrimethylsilyl monophosphoryl lipid A
[Spectrum 0077]
Chemical shifts (ppm) and coupling constants (J, in Hz) of protons of dimethyl pentatrimethylsilyl monophosphoryl lipid A
[Table 0073]



Salmonella tryhimurium(Ref. 1821)




34
2'N-3''hydroxytetradecanoyl, 3'-O-3''hydroxytetradecanoyl b-(1a_right6) D-glucosaminyl 2N-3''hydroxytetradecanoyl, 3-O-3''hydroxytetradecanoyl D-glucosamine 1,4'-bisphosphate
CLS1822
Yoshio Kumazawa
C68H127O23N2P2 1402.683 Download ChemDraw structure file

13C NMR spectra of lipid A precursors
[Spectrum 0078]
Proton NMR spectra at 490 MHz of tetramethyl derivatives of IVA and IVB
[Spectrum 0079]
COSY spectra at 490 MHz of the tetramethyl derivatives of lipid A precursors
[Spectrum 0080]
Phosphorus 31 NMR spectra of lipid A precursors at 80.9 MHz with broad band 1H decoupling
[Spectrum 0081]



Salmonella typhimurium(Ref. 1822)



Carbon-13 assignments for GlcN carbons in lipid A precursors and chemical shifts of relevant model saccharides
[Table 0074]
Carbon-13 chemical shifts of acyl carbons in lipid A precursors
[Table 0075]
1H NMR chemical shifts (in ppm from internal Me4Si) and vicinal coupling constants (J, Hz) for tetramethyl derivatives of lipid A precursors IVA and dimethyl lipid Y
[Table 0076]
Phosphorus 31 chemical shifts and 1H-31P coupling data for lipid A precursors and model compounds at pH 9.7
[Table 0077]
Schematic diagram of the proposed structures of lipid A precursors
[Table 0078]
35
2'N-3''(dodecanoyloxy)tetradecanoyl, 3'-O-3''(tetradecanoyloxy)tetradecanoyl b-(1a_right6) D-glucosaminyl 2N-3''(hexadecanoyloxy)tetradecanoyl, 3-O-3''hydroxytetradecanoyl D-glucosamine 1,4'-bisphosphate
CLS1823
Yoshio Kumazawa
C110H214O26N2P2 2042.822 Download ChemDraw structure file




Paper chromatography of glycolipids synthesized by mutant Ts7 and strain Ts6 at 42degC
[Table 0083]
DEAE-cellulose chromatography of radioactive glycolipid A from mutant Ts7
[Table 0084]
Salmonella typhimurium(Ref. 1823)



Properties of the Salmonella mutants employed
[Table 0079]
Dependence of electrophoretic mobilities on the structure of lipopolysaccharides
[Table 0080]
Composition of the glycolipid product synthesized by mutant Ts7 at 42degC after DEAE-cellulose chromatography
[Table 0081]
Profile of 3H dadioactivity following a first and second enrichment of lipid A mutants using free-flow electrophoresis
[Table 0082]
Electrophoretic mobilities of mutant Ts7 and parent Ts6 following a shift from 30degC to 42degC
[Table 0085]
36
Lipid A from Escherichia coli
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2001
Shoichi Kusumoto
#506, LA-15-PH
C94H178N2O25P2 1798.365 Download ChemDraw structure file
IL-6 induction, TNF-a induction, Limulus activity ED50; (Ref. 2001)
1H NMR (600 MHz, CD3OD / CDCl3 = 1 : 1) d = 5.47 (dd, J= 5.8, 2.9 Hz, 1H), 5.24-5.16 (m, 3H), 5.09 (t, J= 8.1 Hz, 1H), 4.55 (d, J= 7.0 Hz, 1H), 4.25 (dd, J= 16.0, 7.9 Hz, 1H), 4.18 (m, 1H), 4.13 (m, 1H), 4.07 (d, J= 9.8 Hz, 1H), 4.02 (dd, J= 11.2, 1.8 Hz, 1H), 4.00 (m, 1H), 3.94-3.87 (m, 2H), 3.84 (dd, J= 10.0, 5.0 Hz, 1H), 3.76 (d, J= 11.4 Hz, 1H), 3.49 (t, J= 7.7 Hz, 1H), 3.37 (m, 1H), 2.71 (dd, J= 13.5, 6.2 Hz, 1H), 2.64 (dd, J= 13.5, 4.3 Hz, 1H), 2.51 (dd, J= 12.6, 7.0 Hz, 1H), 2.50 (dd, J= 12.6, 3.7 Hz, 1H), 2.43 (dd, J= 12.6, 4.0 Hz, 1H), 2.41 (dd,J= 13.1, 7.7 Hz, 1H), 2.35-2.29 (m, 4H), 2.26-2.22 (m, 1H), 2.25 (dd, J= 12.0, 8.0 Hz, 1H), 1.67-1.40 (m, 12H), 1.38-1.22 (m, 108H), 0.89 (t, J= 5.9 Hz, 18H).; (Ref. 2001)
FAB-MS (negative) m/z 1797 [(M-H)-]

liquid-liquid partition column chromatography; 20 g of Sephadex LH-20, chroloform / methanol / water / isopropyl alchol = 8 : 8 : 6 : 1
Escherichia coli
Coupling of the trichloroacetimidate donor with the glycosyl acceptor, which were prepared from allyl 4,6-O-benzylidene-2-deoxy-2-(trichloroethoxycarbonylamino)-D-glucopyranoside, was carried out by the use of tin(II) trifluororomethanesulfonate as a catalyst to give the desired b(1a_right6) disaccharide. Acylation of the 3-position with (R)-3-(benzyloxy)-tetradecanoic acid proceeded smoothly. Deprotection of N2,2,2-trichloroethoxycarbonyl group at the 2'-position was followed by N-acylation with (R)-3-(dodecanoyloxy)-tetradecanoic acid by using DCC. For the introduction of the phosphoryl group at the 1-position, the 1-O-allyl group was then removed. The hydroxy group was then phosphorylated with tetrabenzyl diphosphate to give the 1-a-phosphate. Finally, hydrogenolysis (7 kgcm-2 of hydrogen and Pd-black) of all the benzyl-type protecting groups furnished the desired E-coli lipid A.; (Ref. 2001)



37
Biosynthetic precursor of lipid A from Escherichia coli
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2002
Shoichi Kusumoto
#406, LA-14-PP
C68H130N2O23P2 1405.707 Download ChemDraw structure file
IL-6 inhibiting activity; (Ref. 2007)
1H NMR (500 MHz, DMSO-d6) d=8.76(br s, 1H), 7.32 (d, J=9.0Hz, 1H), 5.24 (dd, J=6.6,1.8Hz, 1H), 5.03 (dd, J=9.9,9.9Hz, 1H), 4.89 (dd, J=11.7,6.4Hz, 1H), 4.88 (d, J=8.2Hz, 1H), 4.03 (ddd, J=6.4,6.4,6.4Hz, 1H), 3.98 (m, 1H), 3.95 (ddd, J=9.0,9.0,1,8Hz, 1H), 3.87 (ddd, J=136.0,12.5,2.7Hz, 1H), 3.85,3.83,3.73 and 3.72 (m, 1H each), 3.77(dd, J=11.7,8.2Hz, 1H), 3.75 (m, 1H), 3.70 (ddd, J=140.0,12.5,6.3Hz, 1H), 3.53 (m, 1H), 3.33 (m, 1H), 3.13 (m, 1H), 2.47 (dd, J= 6.7,13.1Hz, 1H), 2.41 (dd, J= 6.7,15.8Hz, 1H), 2.34 (dd, J= 6.7,15.8Hz, 1H),
2.31-2.26, 2.31-2.26, 2.18-2.13, and 2.18-2.13(m, 1H each), 2.08 (dd, J= 5.5,13.1Hz, 1H), 1.44-1.21 (m,80H), 0.92 (t, J=6.9Hz, 12H).; (Ref. 2005)
ESI-MS (negative, API III) m/z 1404.9 [(M-H)-]

liquid-liquid partition column chromatography; Sephadex LH-20, chroloform / methanol / isopropyl alchol / water / triethylamine = 20 : 20 : 2.5 : 22.5 : 0.001
Escherichia coli
Two appropriately modified acyl-substituted glucosamine units were synthesized from D-glucosamine using (R)-3-(benzyloxy)tetradecanoic acid and then coupled by the Lewis acid-promoted glycosidation via the corresponding trichloroacetoimidate. Glycosyl phosphorylation and hydrogenolytic deprotection, followed by purification by liquid-liquid partition chromatography, afforded the target compound in 2.9% total yields through 13 steps from N-Troc D-glucosamine.; (Ref. 2004/2005/2006)



38
Lipid A analogue of shorter acyl chains
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxydecanoyl]-2-O-[(R)-3-hydroxydecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-O-[(R)-3-hydroxydecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2003
Shoichi Kusumoto
C52H98N2O23P2 1181.282 Download ChemDraw structure file

a]d-24 -21.0 (c 0.03, H2O)
1H NMR (500 MHz, D2O) d=5.36(br s, 1H, H1), 5.16 (m, 1H, H3.), 5.15 (m, 1H, H3), 4.63 (m, 1H, H1.), 4.11 (m, 1H, H2), 4.09 (m, 1H, H4.), 4.08 (m, 1H, H6a), 3.99 (m, 1H, H2.), 3.98,3.97,3.92 and 3.92 (m, 1H each, one of oxymethine protons on acyl groups), 3.95 (m, 1H, H5), 3.84 (m, 1H, H6a.), 3.83 (m, 1H, H6b), 3.80 (m, 1H, H4), 3.75 (m, 1H, H6b.), 3.60 (m, 1H, H5.), 2.59 (dd, J=15.9,5.4Hz, 1H, one of a-CH2 protons on acyl groups), 2.50,2.45,2.39,2.38,2.30,2.25 and 2.25 (m, 1H each, one of a-CH2 protons on acyl groups), 1.50-1.16 (m, 48H, CH2 on acyl groups), 0.86-0.76 (m, 12H, CH3 on acyl groups).; (Ref. 2007)
ESI-MS (nagative) m/z 1179.7 [(M-H)-], 589.1 [(M-2H)2-]

liquid-liquid partition column chromatography; Sephadex LH-20, chroloform / methanol / isopropyl alchol / water / triethylamine = 20 : 20 : 2.5 : 22.5 : 0.001

(Ref. 2007)Two appropriately modified acyl-substituted glucosamine units were synthesized from D-glucosamine using (R)-3-(benzyloxy)decanoic acid and then coupled by the Lewis acid-promoted glycosidation via the corresponding trichloroacetoimidate. Glycosyl phosphorylation and hydrogenolytic deprotection, followed by purification by liquid-liquid partition chromatography, afforded the target compound in 2.9% total yields through 13 steps from N-Troc D-glucosamine.



39
Biosynthetic precursor of lipid A analogue of shorter acyl chains
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxydecanoyl]-2-O-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-O-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2004
Shoichi Kusumoto
C60H114N2O23P2 1293.494 Download ChemDraw structure file
IL-6 inhibiting activity; (Ref. 2007)

ESI-MS (nagative) m/z 1291.6 [(M-H)-], 645.3 [(M-2H)2-]

liquid-liquid partition column chromatography; Sephadex LH-20, chroloform / methanol / isopropyl alchol / water / triethylamine = 20 : 20 : 2.5 : 22.5 : 0.001

(Ref. 2007)Two appropriately modified acyl-substituted glucosamine units were synthesized from D-glucosamine using (R)-3-(benzyloxy)decanoic acid and (R)-3-(benzyloxy)tetradecanoic acid then coupled by the Lewis acid-promoted glycosidation via the corresponding trichloroacetoimidate. Glycosyl phosphorylation and hydrogenolytic deprotection, followed by purification by liquid-liquid partition chromatography, afforded the target compound in 2.9% total yields through 13 steps from N-Troc D-glucosamine.



40
6-13C-labeled biosynthetic precursor of lipid A
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-(6-13C)-glucopyranose 1,4'-Bisphosphate
CLS2005
Shoichi Kusumoto
#406, LA-15-PH
C68H130N2O23P2 1405.707 Download ChemDraw structure file
IL-6 inhibiting activity; (Ref. 2001)
1H NMR (500 MHz, DMSO-d6) d=8.76 (br s, 1H), 7.32 (d, J=9.0Hz, 1H), 5.24 (dd, J=6.6,1.8Hz,1H), 5.03 (dd, J=9.9,9.9Hz, 1H), 4.89 (dd, J=11.7,6.4Hz, 1H), 4.88 (d, J=8.2Hz,1H), 4.03 (ddd, J=6.4,6.4,6.4Hz, 1H), 3.98 (m, 1H), 3.95 (ddd, J=9.0,9.0,1,8Hz, 1H), 3.87 (ddd, J=136.0,12.5,2.7Hz, 1H), 3.85,3.83,3.73 and 3.72 (m, 1H), 3.77 (dd, J=11.7,8.2Hz, 1H), 3.75 (m, 1H), 3.70 (ddd, J=140.0,12.5,6.3Hz, 1H), 3.53 (m, 1H), 3.33 (m, 1H), 3.13 (m, 1H), 2.47 (dd, J= 6.7,13.1Hz, 1H),
2.41 (dd, J= 6.7,15.8Hz, 1H), 2.34 (dd, J= 6.7,15.8Hz, 1H), 2.31-2.26, 2.31-2.26, 2.18-2.13, and 2.18-2.13 (m, 1H each), 2.08 (dd, J= 5.5,13.1Hz, 1H), 1.44-1.21 (m, 80H), 0.92 (t, J=6.9Hz,12H); 13C NMR (125.65 MHz, DMSO-d6) d = 66.4 (C6).; (Ref. 2009)
ESI-MS (nagative API III) m/z 1404.9 [(M-H)-]

liquid-liquid partition column chromatography; Sephadex LH-20, chroloform / methanol / isopropyl alchol / water / triethylamine = 20 : 20 : 2.5 : 22.5 : 0.001
Escherichia coli
(Ref. 2009)D-(6-13C)Glucose was converted into a suitably protected glucosamine derivative via 1,6-anhydro-b-D-glucose. After coupling with glycosyl donors, the desired compounds were synthesized through a 6-step reaction sequence. The total yields were 1.7%, respectively, for a total of 18 steps from D-(6-13C)glucose.



41
6-13C-labeled lipid A analogue of shorter acyl chains
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxydecanoyl]-2-O-[(R)-3-hydroxydecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-O-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2006
Shoichi Kusumoto
C52H98N2O23P2 1181.282 Download ChemDraw structure file

[a]d-24 -21.0 (c 0.03, H2O)
1H NMR (500 MHz, D2O) d=5.36 (br s, 1H, H1), 5.16 (m, 1H, H3.), 5.15 (m, 1H, H3), 4.63(m, 1H, H1.), 4.11 (m, 1H, H2), 4.09 (m, 1H, H4.), 4.08 (m, 1H, H6a), 3.99 (m, 1H, H2.), 3.98,3.97,3.92 and 3.92 (m, 1H each, one of oxymethine protons on acyl groups), 3.95 (m, 1H, H5), 3.84 (m, 1H, H6a.), 3.83 (m, 1H, H6b), 3.80 (m, 1H, H4), 3.75 (m, 1H, H6b.), 3.60 (m, 1H, H5.), 2.59 (dd, J=15.9,5.4Hz, 1H, one of a-CH2 protons on acyl groups), 2.50,2.45,2.39,2.38,2.30,2.25 and 2.25 (m, 1H each, one of a-CH2 protons on acyl groups), 1.50-1.16 (m, 48H, CH2 on acyl groups), 0.86-0.76 (m, 12H, CH3 on acyl groups); 13C NMR (125.65 MHz, D2O) d = 68.5 (C6).; (Ref. 2007)
ESI-MS (nagative) m/z 1179.7 [(M-H)-], 589.1 [(M-2H)2-]

liquid-liquid partition column chromatography; Sephadex LH-20, chroloform / methanol / isopropyl alchol / water / triethylamine = 20 : 20 : 2.5 : 22.5 : 0.001

D-(6-13C)Glucose was converted into a suitably protected glucosamine derivative via 1,6-anhydro-b-D-glucose. After coupling with glycosyl donors, the desired compounds were synthesized through a 6-step reaction sequence. The total yields were 6.4%, respectively, for a total of 18 steps from D-(6-13C)glucose.; (Ref. 2009)



42
Lipid A from Escherichia coli hydroxy analogue of fatty acid S-type
2-Deoxy-6-O-[2-deoxy-2-[(S)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(S)-3-(tetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-3-O-[(S)-3-hydroxytetradecanoyl]-2-[(S)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2007
Shoichi Kusumoto
C94H178N2O25P2 1798.365 Download ChemDraw structure file
IL-6 induction; (Ref. 2010)
1H NMR (500 MHz, CDCl3 ) d = 5.55 (dd, J= 5.8, 2.9 Hz, 1H), 5.22-5.18 (m, 4H), 4.77 (d, J= 8.7 Hz, 1H), 4.27-4.21 (m, 2H), 4.09- 4.03 (m, 2H), 3.90-3.75 (m, 6H), 3.55 (dd, J= 9.6, 9.6 Hz, 1H), 3.49 -3.47 (m, 1H), 2.70 (dd, J= 16.7, 4.8 Hz, 1H), 2.62-2.55 (m, 2H), 2.49-2.47 (m, 2H), 2.43-2.35 (m, 2H), 2.34-2.27 (m, 4H), 2.26-2.22 (m, 1H), 1.66-1.54 (m, 8H), 1.53-1.42 (m, 4H), 1.40-1.24 (m, 108H), 0.88 (t, J= 6.9 Hz, 18H).; (Ref. 2010)
FAB-MS (negative) m/z 1797 [(M-H)-]

centrifugal partition chromatography; n-buthanol / THF / water / triethylamine = 45 : 35 : 100 : 0.02, 1600rpm.(Ref. 2010)

Coupling of the trichloroacetimidate donor with the glycosyl acceptor, which were prepared from allyl 4,6-O-benzylidene-2-deoxy-2-(trichloroethoxycarbonylamino)-D-glucopyranoside, was carried out by the use of tin(II) trifluororomethanesulfonate as a catalyst to give the desired b(1a_right6) disaccharide. Acylation of the 3-position with (S)-3-(benzyloxy)-tetradecanoic acid proceeded smoothly. Deprotection of N2,2,2-trichloroethoxycarbonyl group at the 2'-position was followed by N-acylation with (S)-3-(dodecanoyloxy)-tetradecanoic acid. For the introduction of the phosphoryl group at the 1-position, the 1-O-allyl group was then removed. The hydroxy group was then phosphorylated with tetrabenzyl diphosphate to give the 1-a-phosphate. Finally, hydrogenolysis (7 kgcm-2 of hydrogen and Pd-black) of all the benzyl-type protecting groups furnished the desired E-coli lipidA.; (Ref. 2010)



43
Biosynthetic precursor of lipid A analogue with hydroxy fatty acid S-type
2-Deoxy-6-O-[2-deoxy-3-O-[(S)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(S)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2008
Shoichi Kusumoto
C68H130N2O23P2 1405.707 Download ChemDraw structure file
IL-6 inhibiting activity; (Ref. 2010)

FAB-MS (nagative) m/z 1403 [(M-H)-]

centrifugal partition chromatography; n-buthanol / THF / water / triethylamine = 45 : 35 : 100 : 0.02, 1600rpm.; (Ref. 2010)

Two appropriately modified acyl-substituted glucosamine units were synthesized from D-glucosamine using (R)-3-(benzyloxy)tetradecanoic acid and then coupled by the Lewis acid-promoted glycosidation via the corresponding trichloroacetoimidate. Glycosyl phosphorylation and hydrogenolytic deprotection afforded the target compound through 13 steps from N-Troc D-glucosamine.; (Ref. 2004/2005/2006)



44
a-phosphonooxyethyl analogue of lipid A from Escherichia coli
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-4-O-phosphono-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-1-O-(phosphonooxy)ethyl -a-D-glucopyranoside
CLS2009
Shoichi Kusumoto
#PE-1
C96H182N2O26P2 1842.418 Download ChemDraw structure file
IL-6 induction, TNF-a induction, Limulus activity ED50 2 pg/mL; (Ref. 2011)
1H NMR(600 MHz, CD3OD/CDCl3 =1:1) d = 5.23 (m, 1H), 5.19 (t, J= 8.2 Hz, 1H), 5.17 (m, 1H), 5.14 (t, J= 8.2 Hz, 1H), 4.82(d, J= 3.0 Hz, 1H), 4.56(d, J= 7.4 Hz, 1H), 4.23(q, J= 8.0 Hz, 1H), 4.18 (dd, J= 8.9,3.0 Hz, 1H), 4.08-3.93 (m, 5H), 3.92- 3.82 (m, 4H), 3.80 (dd, J= 10.3,4.5 Hz, 1H), 3.74 (d, J= 10.6 Hz, 1H), 3.63 (m, 1H), 3.56 (t, J= 8.1 Hz, 1H), 3.37 (m, 1H), 2.72 (dd, J= 14.0, 6.6 Hz, 1H), 2.64 (dd, J= 14.0,4.5 Hz, 1H), 2.52-2.36 (m, 2H), 2.36-2.27 (m, 6H), 1.66-1.39 (m, 12H), 1.38-1.20 (m, 108H), 0.89 (t, J= 5.6 Hz, 18H).; (Ref. 2011)
FAB-MS (negative) m/z 1840 [(M-H)-]

liquid-liquid partition column chromatography; 20 g of Sephadex LH-20, chroloform / methanol / water / isopropyl alchol = 15 : 15: 15 : 2




45
a-carboxymethyl analogue of lipid A from Escherichia coli
1-O-Carboxymethyl-2-deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-4-O-phosphoryl-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose
CLS2010
Shoichi Kusumoto
#CM-506
C96H179N2O24P 1776.421 Download ChemDraw structure file
IL-6 induction, TNF-a induction, Limulus activity ED50 1 pg/mL; (Ref. 2011)
1H NMR(600 MHz, CD3OD/CDCl3 =1:1) d = 5.26-5.17 (m, 2H), 5.23 (t, J= 8.4 Hz, 1H), 5.16 (t, J= 9.1 Hz, 1H), 4.78 (d, J= 3.1 Hz, 1H), 4.65 (d, J= 6.9 Hz, 1H), 4.20-4.14 (m, 2H), 4.09(d, J= 12.5 Hz, 1H), 4.08-3.98 (m, 2H), 3.94 (m, 1H), 3.86 (d, J= 12.5 HZ, 1H), 3.91-3.65 (m, 5H), 3.52(t, J= 8.0 Hz, 1H), 3.36 (m, 1H), 2.82 (dd, J= 13.7, 5.4 Hz, 1H), 2.64 (dd, J= 13.7, 4.7 Hz, 1H), 2.54-2.36 (m, 4H), 2.36-2.24 (m, 6H), 1.68-1.40 (m, 12H), 1.39-1.21 (m, 108H), 0.89 (t, J= 5.8 Hz, 18H).; (Ref. 2011)
FAB-MS (negative) m/z 1774[(M-H)-]

liquid-liquid partition column chromatography; 20 g of Sephadex LH-20, chroloform / methanol / water / isopropyl alchol = 100 : 100: 100 : 13




46
a-phosphonooxyethyl analogue of lipid A from Escherichia coli with nonhydroxylated lipid
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-4-O-phosphoryl-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-1-O-(phosphonooxy)ethyl-3-O-[(R)-tetradecanoyl]-2-[(R)-tetradecanoylamino]-a-D-glucopyranoside
CLS2011
Shoichi Kusumoto
#PE-2
C96H182N2O24P2 1810.419 Download ChemDraw structure file
IL-6 induction, TNF-a induction; (Ref. 2012)








47
b-phosphonooxyethyl analogue of lipid A from Escherichia coli
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-4-O-phosphonyl-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-1-O-(phosphonooxy)ethyl-3-O-[(R)-tetradecanoyl]-2-[(R)-tetradecanoylamino]-b-D-glucopyranoside
CLS2012
Shoichi Kusumoto
#PE-3
C96H182N2O24P2 1810.419 Download ChemDraw structure file
IL-6 induction, TNF-a induction; (Ref. 2012)








48
a-phosphonooxyethyl analogue of biosynthetic precursor of lipid A from Eschericha coli
2-(Phosphonooxy)ethyl-2-deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranoside
CLS2013
Shoichi Kusumoto
#PE-4
C70H134N2O24P2 1449.760 Download ChemDraw structure file
IL-6 induction, TNF-a induction; (Ref. 2012)

ESI-MS (nagative, API III) m/z 1404.9 [(M-H)-]






49
a-carboxymethyl analogue of biosynthetic precursor of lipid A from Eschericha coli
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranosyl-oxyacetic Acid
CLS2014
Shoichi Kusumoto
#CM-406
C96H179N2O24P 1776.421 Download ChemDraw structure file









50
Lipid A from Helicobactor pylori strain 206-1
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(octadecanoyloxy)octadecanoylamino]-b-D-glucopyranosyl]-2-[(R)-3-hydroxyoctadecanoylamino]-a-D-glucopyranose 1-(2-Aminoethyl)phosphate
CLS2015
Shoichi Kusumoto
C68H132N3O17P 1294.759 Download ChemDraw structure file
IL-6 induction, TNF-a induction, Limulus activity ED50; (Ref. 2018)
1H NMR; (Ref. 2016/2018)
ESI-MS (negative) m/z 1293.0 [(M-H)-]; (Ref. 2016/2018)


Helicobacter pylori strain 206-1



51
analogue of Lipid A from Helicobactor pylori strain 206-1 without ethanolamine
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(octadecanoyloxy)octadecanoylamino]-b-D-glucopyranosyl]-2-[(R)-3-hydroxyoctadecanoylamino]-a-D-glucopyranose 1-Phosphate
CLS2016
Shoichi Kusumoto
C66H127N2O17P 1251.692 Download ChemDraw structure file

1H NMR; (Ref. 2017)






52
Lipid A from Helicobactor pylori strain 206 tetra-acyl type
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(octadecanoyloxy)octadecanoylamino]-b-D-glucopyranosyl]-3-O-(R)-3-hydroxyhexadecanoyl-2-[(R)-3-hydroxyoctadecanoylamino]-a-D-glucopyranose 1-(2-Aminoethyl)phosphate
CLS2017
Shoichi Kusumoto
#206-2
C84H162N3O19P 1549.168 Download ChemDraw structure file
IL-6 induction, TNF-a induction, Lethal toxicity LD50, Limulus activity; (Ref. 2018)
1H NMR, 31P NMR; (Ref. 2018)
ESI-MS (negative) m/z 1548 [(M-H)-]; (Ref. 2018)


Helicobacter pylori strain 206




53
Lipid A from Haemophilus influenzae
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2018
Shoichi Kusumoto
C96H182N2O25P2 1826.418 Download ChemDraw structure file
IL-6 induction, TNF-a induction, Limulus activity ED50; (Ref. 2019)




Haemophilus influenzae strain I-6P Rd-/b+; (Ref. 5019)(Ref. 5021)




54
Lipid A from Helicobactor pylori hexa-acyl type C12
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(dodecanoyloxy)hexadecanoyl]-2-[(R)-3-(octadecanoyloxy)octadecanoylamino]-4-O-phosphoryl-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxyhexadecanoyl]-2-[(R)-3-hydroxyoctadecanoylamino]-a-D-glucopyranose 1-(2-Aminoethyl)phosphate
CLS2019
Shoichi Kusumoto
C112H215N3O25P2 2065.858 Download ChemDraw structure file

liquid-liquid partition column chromatography; 20 g of Sephadex LH-20, 1-butanol / THF/ methanol / water / = 13 : 7 : 1 : 20
Helicobacter pilori, S-LPS; (Ref. 5021)




55
Lipid A from Helicobactor pylori hexa-acyl type C14
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)hexadecanoyl]-2-[(R)-3-(octadecanoyloxy)octadecanoylamino]-4-O-phosphoryl-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxyhexadecanoyl]-2-[(R)-3-hydroxyoctadecanoylamino]-a-D-glucopyranose 1-(2-Aminoethyl)phosphate
CLS2020
Shoichi Kusumoto
C114H219N3O25P2 2093.911 Download ChemDraw structure file

liquid-liquid partition column chromatography; 20 g of Sephadex LH-20, 1-butanol / THF/ methanol / water / = 13 : 7 : 1 : 20
Helicobacter pilori, S-LPS; (Ref. 5021)




56
Lipid A from Enterobactor agglomerans
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-(hexadecanoyloxy)tetradecanoylamino-3-O-[(R)-3-hydroxytetradecanoyl]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2021
Shoichi Kusumoto
C110H208N2O26P2 2036.774 Download ChemDraw structure file




Enterobactor agglomerans




57
Lipid A from Enterobactor agglomerans
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-(3-hydroxytetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-(hexadecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxytetradecanoyl]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2022
Shoichi Kusumoto
C110H208N2O27P2 2052.773 Download ChemDraw structure file




Enterobactor agglomerans




58
Lipid A from Pantoea agglomerans
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-(3-hydroxytetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-(hexadecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxytetradecanoyl]-a-D-glucopyranose 4'-Phosphate
CLS2023
Shoichi Kusumoto
C110H207N2O23P 1956.794 Download ChemDraw structure file

1H NMR, 13C NMR; (Ref. 2024)
FAB-MS (positive, dimethyl-form) m/z 2008 [(M+Na)+]; (Ref. 2024)

silicagel column chromatography: CHCl3/CH3OH/H2O/(CH3-CH2)3N (87:12:1:0.2, 85:14:1:0.2, 83:16:1:0.2, v/v); (Ref. 2024)
Enterobactor agglomerans; (Ref. 5024)




59
Lipid A from Moraxella catahalis
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(decanoyloxy)dodecanoylamino]-3-O-[(R)-3-hydoroxydecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-(decanoyloxy)dodecanoyl]-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2024
Shoichi Kusumoto
C92H172N2O26P2 1784.295 Download ChemDraw structure file



Enterobactor agglomerans




60
Lipid A from Erwinia carotovora
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(dodecanoyloxy)decanoyl]-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2025
Shoichi Kusumoto
C92H174N2O25P2 1770.312 Download ChemDraw structure file
Limulus test, TNFa induction; (Ref. 2027)
MALDI-TOF-MS (negative) m/z 1769.4 [(M-H)-]; (Ref. 2026/2027)


Erwinia carotovora




61
Lipid A from Erwinia carotovora heptaacyl type
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(dodecanoyloxy)decanoyl]-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-2-[(R)-3-(hexadecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxytetradecanoyl]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2026
Shoichi Kusumoto
C108H204N2O26P2 2008.721 Download ChemDraw structure file
Limulus test, TNFa induction; (Ref. 2027)
MALDI-TOF-MS (negative) m/z 2007.8 [(M-H)-]; (Ref. 2026/2027)


Erwinia carotovora




62
Lipid A from Salmonella enterica sv Minnesota LPS R595
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-(hexadecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxytetradecanoyl]-a-D-glucopyranose 4'-Phosphate
CLS2027
Shoichi Kusumoto
C110H207N2O24P 1972.793 Download ChemDraw structure file

FAB-MS (positive, dimethyl-form) m/z 1983.3; (Ref. 2028)


Salmonella enterica sv Minnesota R595




63
Lipid A from Campylobacter jejuni
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(hexadecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-(hexadecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2028
Shoichi Kusumoto
C100H190N2O25P2 1882.525 Download ChemDraw structure file


Campylobacter jejuni




64
Lipid A from Haemophilus ducreyi
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2029
Shoichi Kusumoto
C96H182N2O25P2 1826.418 Download ChemDraw structure file




Haemophilus ducreyi




65
Lipid A from Klebsiella pneumoniae
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-2-[(R)-3-(hexadecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxytetradecanoyl]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2030
Shoichi Kusumoto
C112H212N2O26P2 2064.827 Download ChemDraw structure file




Klebsiella pneumoniae




66
Lipid A from Legionella pneumophila
2-Deoxy-6-O-[2,3-dideoxy-2-[(R)-3-(hexadecanoyloxy)icosadecanoylamino]-3-O-[(R)-3-(octacosanoyloxy)icosadecanoylamino]-b-D-glucopyranosyl]-2-[(R)-3-hydroxyicosanoylamino]-3-O-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2031
Shoichi Kusumoto
C124H240N4O23P2 2217.193 Download ChemDraw structure file




Legionella pneumophila




67
Lipid A from Pectinatus cerevisiiphilus
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(undecanoyloxy)triradecanoyl]-2-[(R)-3-(undecanoyloxy)tridecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2032
Shoichi Kusumoto
C88H166N2O25P2 1714.206 Download ChemDraw structure file




Pectinatus cerevisiiphilus




68
Lipid A from Pectinatus frisingesis
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(tridecanoyloxy)tridecanoylamino]-3-O-[(R)-3-(undecanoyloxy)triradecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2033
Shoichi Kusumoto
C90H170N2O25P2 1742.259 Download ChemDraw structure file




Pectinatus frisingesis




69
Lipid A from Providencia rettgeri
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tretradecanoyl]-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2034
Shoichi Kusumoto
C96H182N2O25P2 1826.418 Download ChemDraw structure file




Providencia rettgeri




70
Lipid A from Proteus mirabilis
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-(tetradecanoyloxy)tretradecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-(hexadecanoyloxy)tetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2035
Shoichi Kusumoto
C112H212N2O26P2 2064.827 Download ChemDraw structure file




Proteus mirabilis



71
Lipid A from Rhodospirillum fulvum
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(hexadecanoyloxy)hexadecanoylamino]-3-O-[(R)-3-(dodecanoyloxy)tretradecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose
CLS2036
Shoichi Kusumoto
C100H188N2O19 1722.565 Download ChemDraw structure file


Rhodospirillum fulvum




72
Lipid A from Salmonella Typhimurium
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)decanoyl]-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 4'-Phosphate
CLS2037
Shoichi Kusumoto
C94H177N2O22P 1718.385 Download ChemDraw structure file


HPLC; (Ref. 2041)
Salmonella enterica sv.Typhimurium




73
Lipid A from Chromobacterium violaceum
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)dodecanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-(dodecanoyloxy)dodecanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2038
Shoichi Kusumoto
C80H150N2O25P2 1601.993 Download ChemDraw structure file




Chromobacterium violaceum




74
Lipid A from Comamonas testosteroni
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)decanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-(tetradecanoyloxy)decanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2039
Shoichi Kusumoto
C77H144N2O25P2 1559.913 Download ChemDraw structure file


Comamonas testosteroni




75
Lipid A from Neisseria gonorrhoeae hexaacyl type
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)decanoylamino]-3-O-[(R)-3-hydroxytetradecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxytetradecanoyl]-a-D-glucopyranose 4'-Phosphate
CLS2040
Shoichi Kusumoto
C88H165N2O22P 1634.226 Download ChemDraw structure file


HPLC, TLC; (Ref. 2045)
Neisseria gonorrhoeae




76
Lipid A from Neisseria gonorrhoeae pentaacyl type
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)decanoylamino]-3-O-[(R)-3-hydroxytetradecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 4'-Phosphate
CLS2041
Shoichi Kusumoto
C76H143N2O21P 1451.923 Download ChemDraw structure file


HPLC, TLC; (Ref. 2045)
Neisseria gonorrhoeae




77
Lipid A from Neisseria meningitidis
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxydodecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxydodecanoyl]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2042
Shoichi Kusumoto
C88H166N2O25P2 1714.206 Download ChemDraw structure file




Neisseria meningitidis




78
Lipid A from Plesiomonas shigelloides
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxytetradecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2043
Shoichi Kusumoto
C94H178N2O25P2 1798.365 Download ChemDraw structure file




Plesiomonas shigelloides




79
Lipid A from Rhodopseudomonas gelantinosa
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)decanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-(tetradecanoyloxy)decanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2044
Shoichi Kusumoto
C78H146N2O25P2 1573.940 Download ChemDraw structure file




Rhodopseudomonas gelantinosa




80
Lipid A from Shigella sonnei
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2045
Shoichi Kusumoto
C90H170N2O25P2 1742.259 Download ChemDraw structure file

31P NMR; (Ref. 2049)



Shigella sonnei




81
Lipid A from Bordetella pertussis
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2046
Shoichi Kusumoto
C78H148N2O24P2 1559.956 Download ChemDraw structure file



TLC, gas-liquid chromatography; (Ref. 2050)
Bordetella pertussis




82
Lipid A from Chlamydia trachomatis-1
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(octadecanoyloxy)icosanoylamino]-3-O-[(R)-tetradecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-hydroxyicosanoylamino]-3-O-[(R)-tetradecanoyl]-a-D-glucopyranose 4'-Phosphate
CLS2047
Shoichi Kusumoto
C98H187N2O19P 1728.509 Download ChemDraw structure file



reverse-phase HPLC; (Ref. 2051)
Chlamydia trachomatis




83
Lipid A from Chlamydia trachomatis-2
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(nonadecanoyloxy)icosanoylamino]-3-O-[(R)-pentadecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-hydroxyicosanoylamino]-3-O-[(R)-pentadecanoyl]-a-D-glucopyranose 4'-Phosphate
CLS2048
Shoichi Kusumoto
C101H193N2O19P 1770.589 Download ChemDraw structure file



reverse-phase HPLC; (Ref. 2051)
Chlamydia trachomatis




84
Lipid A from Chlamydia trachomatis-3
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-hexadecanoyl]-2-[(R)-3-(icosadecanoyloxy)icosanoylamino]-b-D-glucopyranosyl]-2-[(R)-3-hydroxyicosanoylamino]-3-O-[(R)-pentadecanoyl]-a-D-glucopyranose 4'-Phosphate
CLS2049
Shoichi Kusumoto
C103H197N2O19P 1798.642 Download ChemDraw structure file



reverse-phase HPLC; (Ref. 2051)
Chlamydia trachomatis




85
Lipid A from Escherichia coli msbB mutant
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxytetradecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2050
Shoichi Kusumoto
C80H152N2O24P2 1588.009 Download ChemDraw structure file




Escherichia coli




86
Lipid A from Bacteroides fragilis strain NCTC 9343
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(13-methyltetradecanoyloxy)-15-methylhexadecanoylamino]-3-O-[(R)-3-hydroxyhexadecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxypentadecanoyl]-2-[(R)-3-hydroxyhexadecanoylamino]-a-D-glucopyranose 1-Phosphate
CLS2051
Shoichi Kusumoto
C91H173N2O21P 1662.322 Download ChemDraw structure file




Bacteroides fragilis strain NCTC 9343




87
Lipid A from Bacteroides fragilis
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(13-methyltetradecanoyloxy)hexadecanoylamino]-3-O-[(R)-3-hydroxypentadecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxyhexadecanoyl]-2-[(R)-3-hydroxy-15-methylhexadecanoylamino]-a-D-glucopyranose 1-Phosphate
CLS2052
Shoichi Kusumoto
C91H173N2O21P 1662.322 Download ChemDraw structure file




Bacteroides fragilis




88
Lipid A from Porphyromonas (Bacteroides) gingivalis
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(hexadecanoyloxy)-15-methylhexadecanoylamino]-3-O-[(R)-3-hydroxy-13-methylpentadecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxyhexadecanoyl]-2-[(R)-3-hydroxy-15-methylhexadecanoylamino]-a-D-glucopyranose 1-Phosphate
CLS2053
Shoichi Kusumoto
C93H177N2O21P 1690.375 Download ChemDraw structure file


Porphyromonas (Bacteroides) gingivalis




89
Lipid A from Porphyromonas (Bacteroides) gingivalis triacyl type
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(hexadecanoyloxy)-15-methylhexadecanoylamino]-b-D-glucopyranosyl]-2-[(R)-3-hydroxy-15-methylhexadecanoylamino]-a-D-glucopyranose 1-Phosphate
CLS2054
Shoichi Kusumoto
C62H119N2O17P 1195.585 Download ChemDraw structure file


Porphyromonas (Bacteroides) gingivalis




90
Lipid A from Pseudomonas aeruginosa hexaacyl type
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)dodecanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-(dodecanoyloxy)dodecanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2055
Shoichi Kusumoto
C83H156N2O25P2 1644.073 Download ChemDraw structure file



Pseudomonas aeruginosa




91
Lipid A from Pseudomonas aeruginosa pentaacyl type
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)dodecanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-(dodecanoyloxy)dodecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2056
Shoichi Kusumoto
C71H134N2O23P2 1445.771 Download ChemDraw structure file



Pseudomonas aeruginosa




92
Lipid A from Pseudomonas aeruginosa hexaacyl, 2-hydroxy fatty acid type
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-[2-(S)-hydroxydodecanoyloxy]dodecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-[2-(S)-hydroxydodecanoyloxy]dodecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2057
Shoichi Kusumoto
C83H156N2O27P2 1676.072 Download ChemDraw structure file



Pseudomonas aeruginosa




93
Lipid A from Pseudomonas aeruginosa pentaacyl, 2-hydroxy fatty acid type
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-[2-(S)-hydroxydodecanoyloxy]dodecanoylamino]-b-D-glucopyranosyl]-2-[(R)-3-[2-(S)-hydroxydodecanoyloxy]dodecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2058
Shoichi Kusumoto
C71H134N2O25P2 1477.770 Download ChemDraw structure file



Pseudomonas aeruginosa




94
Lipid A from Pseudomonas fluorescens hexaacyl type
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)dodecanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-(dodecanoyloxy)dodecanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-a-D-glucopyranose 1-(2-Aminoethyl)phosphono, 4'-phosphate
CLS2059
Shoichi Kusumoto
C85H161N3O25P2 1687.141 Download ChemDraw structure file




Pseudomonas fluorescens




95
Lipid A from Pseudomonas fluorescens hexaacyl, 2-hydroxy fatty acid type
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-[2-(S)-hydroxydodecanoyloxy]dodecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-[2-(S)-hydroxydodecanoyloxy]dodecanoylamino]-a-D-glucopyranose 1-(2-Aminoethyl)phosphono, 4'-phosphate
CLS2060
Shoichi Kusumoto
C85H161N3O27P2 1719.139 Download ChemDraw structure file




Pseudomonas fluorescens




96
Lipid A from Rhodopseudomonas sphaeroides
2-Deoxy-6-O-[2-deoxy-2-[3-(7-tetradecenoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1-Phosphate
CLS2061
Shoichi Kusumoto
C74H135N2O21P 1419.838 Download ChemDraw structure file



HPLC; (Ref. 2059)
Rhodopseudomonas sphaeroides ATCC17023




97
Lipid A from Rhodopseudomonas sphaeroides -2
2-Deoxy-6-O-[2-deoxy-2-[3-(7-tetradecenoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1-Phosphate
CLS2062
Shoichi Kusumoto
C74H137N2O21P 1421.854 Download ChemDraw structure file



Rhodopseudomonas sphaeroides ATCC17023




98
Lipid A from Rhodopseudomonas sphaeroides -3
2-Deoxy-6-O-[2-deoxy-2-[3-(tetradecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1-Phosphate
CLS2063
Shoichi Kusumoto
C74H139N2O21P 1423.870 Download ChemDraw structure file



Rhodopseudomonas sphaeroides ATCC17023




99
Lipid A from Rhodobacter capsulatus
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanoyl]-2-[3-oxotetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2064
Shoichi Kusumoto
RcLA
C72H130N2O24P2 1469.749 Download ChemDraw structure file
Nontoxic


Rhodobacter capsulatus




100
Lipid A from Shigella flexneri
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxytetradecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2065
Shoichi Kusumoto
C80H152N2O24P2 1588.009 Download ChemDraw structure file




Shigella flexneri




101
Lipid A from Shigella flexneri
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2066
Shoichi Kusumoto
C94H178N2O25P2 1798.365 Download ChemDraw structure file




Shigella flexneri




102
Lipid A from Sphaerotilus natans
2-Deoxy-6-O-[4-O-(2-aminoethyl)pyrophosphono-2-deoxy-2-[(R)-3-(dodecanoyloxy)decanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-hydroxydecanoylamino]-a-D-glucopyranose 1-Phosphate
CLS2067
Shoichi Kusumoto
C66H126N3O27P3 1486.632 Download ChemDraw structure file




Sphaerotilus natans




103
Lipid A from Sphaerotilus natans
2-Deoxy-6-O-[4-O-(2-aminoethyl)pyrophosphono-2-deoxy-2-[(R)-3-hydroxydecanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-(dodecanoyloxy)decanoylamino]-a-D-glucopyranose 1-Phosphate
CLS2068
Shoichi Kusumoto
C66H126N3O27P3 1486.632 Download ChemDraw structure file




Sphaerotilus natans




104
Lipid A from Rhizobium meliloti
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-hydroxyoctadecanoylamino]-3-O-[(R)-27-hydroxyoctacosadecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxyoctadecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2069
Shoichi Kusumoto
C90H174N2O24P2 1730.291 Download ChemDraw structure file




Rhizobium meliloti




105
Lipid A from Rhizobium leguminosarum bv. phaseoli
2-Deoxy-6-O-[[4-O-a-D-galacturopyranosyl]-2-deoxy-2-[(R)-3-hydroxytetradecanoylamino]-3-O-[(R)-3-hydroxyoctadecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-hydroxyhexadecanoylamino]-5-O-[(R)-27-hydroxyoctacosanoyl]-4-O-[(R)-3-hydroxyoctadecanoyl]-3-O-[(R)-3-hydroxytetradecanoyl]-a-D-gluconic acid
CLS2070
Shoichi Kusumoto
C128H240N2O28 2255.272 Download ChemDraw structure file



Rhizobium leguminosarum bv. phaseoli




106
Lipid A from Actinobacillus actinomycetemcomitans
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 4'-Phosphate
CLS2071
Shoichi Kusumoto
C96H181N2O22P 1746.438 Download ChemDraw structure file




Actinobacillus actinomycetemcomitans




107
Lipid A from Rhodocyclus gelatinosus
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)decanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-(tetradecanoyloxy)decanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2072
Shoichi Kusumoto
C78H146N2O25P2 1573.940 Download ChemDraw structure file
FT-IR; (Ref. 2068)
31P NMR; (Ref. 2069)
LD-MS; (Ref. 2069)
Synchroton radiation X-ray diffraction; (Ref. 2068)

Rhodocyclus gelatinosus




108
Lipid A from Neisseria meningitidis
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxydodecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxydodecanoyl]-a-D-glucopyranose 1,4'-Bis(2-aminoethyl)pyrophosphate
CLS2073
Shoichi Kusumoto
C92H178N4O31P4 1960.301 Download ChemDraw structure file



Neisseria meningitidis




109
Synthetic Lipid A of Rhodomicrobium vannielii type
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-hydroxytetradecanoylamino]-6-O-[b-D-mannnopyranosyl]-b-D-glucopyranosyl]-2-[(R)-3-hydroxytetetradecanoylamino]-a-D-glucopyranose
CLS2074
Shoichi Kusumoto
C46H86N2O18 955.178 Download ChemDraw structure file








110
Synthetic Lipid A of Rhodomicrobium vannielii type
2-Deoxy-6-O-[2-deoxy-6-O-[b-D-mannopyranosyl]-2-[(R)-3-(octanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-2-[(R)-3-(octanoyloxy)tetradecanoylamino]-a-D-glucopyranose
CLS2075
Shoichi Kusumoto
C62H114N2O20 1207.570 Download ChemDraw structure file



Rhodomicrobium vannielii ATCC 17100




111
Lipid A from Helicobacter mustelae II
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-(tetradecanoyloxy)hexadecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxyhexadecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2076
Shoichi Kusumoto
C100H190N2O26P2 1898.524 Download ChemDraw structure file

1H NMR, 31P NMR; (Ref. 2071)
MALDI-TOF MS (negative) m/z 1897 [(M-H)-]; (Ref. 2071)


Helicobacter mustelae strain ATCC 43772




112
Lipid X of Escherichia coli
2-Deoxy--3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetraadecanoylamino]-a-D-glucopyranose 1-Phosphate
CLS2077
Shoichi Kusumoto
Lipid X
C34H66NO12P 711.861 Download ChemDraw structure file




Eschrichia coli



113
Trisubstituted right-half of lipid A
2-Deoxy--3-O-[(R)-3-(decanoyloxy)tetradecanoyl]-2-[(R)-3-hydroxytetraadecanoylamino]-a-D-glucopyranose 1-Phosphate
CLS2078
Shoichi Kusumoto
ERI-1
C44H84NO13P 866.110 Download ChemDraw structure file









114
Carboxymethyl 2-deoxy-2-(2,2-difluorotetradecanoylamino)-4-phosphono-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-a-D-glucopyranoside
CLS2079
Shoichi Kusumoto
Sankyo-1
C51H94F2NO13P 998.262 Download ChemDraw structure file
Inhibition of LPS-induced TNF-a: 5nM; (Ref. 2079)
1H NMR; (Ref. 2079)







115
Carboxymethyl 2-deoxy-2-tetradecanoylamino-4-phosphono-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-a-D-glucopyranoside
CLS2080
Shoichi Kusumoto
Sankyo-2
C51H94F2NO13P 998.262 Download ChemDraw structure file
Inhibition of LPS-induced TNF-a: 17nM; (Ref. 2079)
1H NMR; (Ref. 2079)







116
6-O-Methyl type of lipid A from Rhodobacter capsulatus
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanoyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1, 4'-Bisphosphate
CLS2081
Shoichi Kusumoto
sRcLA
C73H132N2O24P2 1483.776 Download ChemDraw structure file
IC50:5.9pm2.4 nM; (Ref. 2080)









117
O-3' Deacyl type of lipid A from Rhodobacter capsulatus
2-Deoxy-6-O-[2-deoxy-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1, 4'-Bisphosphate
CLS2082
Shoichi Kusumoto
ERI-2
C50H92N2O21P2 1119.214 Download ChemDraw structure file









118
O-3-Deacyl type of lipid A from Rhodobacter capsulatus
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanoyl]-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2083
Shoichi Kusumoto
ERI-3
C62H112N2O22P2 1299.500 Download ChemDraw structure file









119
O-3'-Deacyloxy type of lipid A from Rhodobacter capsulatus
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-2-trans-decenoyl]-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2084
Shoichi Kusumoto
ERI-4
C60H108N2O22P2 1271.447 Download ChemDraw structure file









120
O-3-Deacyl-O-3'-deacyloxy type of lipid A from Rhodobacter capsulatus
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-2-trans-decenoyl]-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2085
Shoichi Kusumoto
ERI-5
C50H90N2O20P2 1101.199 Download ChemDraw structure file









121
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2086
Shoichi Kusumoto
ERI-6
C72H134N2O22P2 1441.782 Download ChemDraw structure file








122
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-4-O-methyl-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2087
Shoichi Kusumoto
ERI-7
C74H138N2O22P2 1469.835 Download ChemDraw structure file








123
4-O-Acetyl-2-deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2088
Shoichi Kusumoto
ERI-8
C75H138N2O23P2 1497.845 Download ChemDraw structure file








124
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-galactopyranose 1,4'-Bisphosphate
CLS2089
Shoichi Kusumoto
ERI-9
C73H136N2O22P2 1455.809 Download ChemDraw structure file








125
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 4'-Phosphate
CLS2090
Shoichi Kusumoto
ERI-10
C73H135N2O9P 1215.835 Download ChemDraw structure file








126
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1-Phosphate
CLS2091
Shoichi Kusumoto
ERI-11
C73H135N2O9P 1215.835 Download ChemDraw structure file








127
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-[3-(R)-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2092
Shoichi Kusumoto
ERI-12
C73H134N2O24P2 1485.792 Download ChemDraw structure file








128
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-[3-(S)-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2093
Shoichi Kusumoto
ERI-13
C73H134N2O24P2 1485.792 Download ChemDraw structure file








129
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-2-[(R)-3-hydroxytetradecanoylamino]-6-O-methyl-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2094
Shoichi Kusumoto
ERI-14
C73H134N2O24P2 1485.792 Download ChemDraw structure file








130
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-2-[(S)-3-hydroxytetradecanoylamino]-6-O-methyl-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2095
Shoichi Kusumoto
ERI-15
C73H134N2O24P2 1485.792 Download ChemDraw structure file








131
3-O-[(R)-3-Acetoxydecanyl]-2-deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2096
Shoichi Kusumoto
ERI-16
C75H138N2O23P2 1497.845 Download ChemDraw structure file








132
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-methoxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2097
Shoichi Kusumoto
ERI-17
C74H138N2O22P2 1469.835 Download ChemDraw structure file








133
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(S)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2098
Shoichi Kusumoto
ERI-18
C73H136N2O22P2 1455.809 Download ChemDraw structure file








134
2-Deoxy-6-O-[2-deoxy-3-O-[(S)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2099
Shoichi Kusumoto
ERI-19
C73H136N2O22P2 1455.809 Download ChemDraw structure file








135
2-Deoxy-6-O-[2-deoxy-3-O-[(S)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(S)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2100
Shoichi Kusumoto
ERI-20
C73H136N2O22P2 1455.809 Download ChemDraw structure file








136
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxydecanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2101
Shoichi Kusumoto
ERI-21
C61H116N2O21P2 1275.522 Download ChemDraw structure file








137
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-trans-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2102
Shoichi Kusumoto
ERI-22
C73H136N2O22P2 1455.809 Download ChemDraw structure file








138
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5,7-cis-dodecadienoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2103
Shoichi Kusumoto
ERI-23
C73H134N2O22P2 1453.793 Download ChemDraw structure file








139
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(dodecanoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2104
Shoichi Kusumoto
ERI-24
C73H138N2O22P2 1457.825 Download ChemDraw structure file








140
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxyoctyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2105
Shoichi Kusumoto
ERI-25
C71H132N2O22P2 1427.756 Download ChemDraw structure file








141
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecayl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2106
Shoichi Kusumoto
ERI-26
C77H144N2O22P2 1511.915 Download ChemDraw structure file








142
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)octyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxyoctyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2107
Shoichi Kusumoto
ERI-27
C69H128N2O22P2 1399.702 Download ChemDraw structure file








143
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)tetradecanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2108
Shoichi Kusumoto
ERI-28
C81H152N2O22P2 1568.021 Download ChemDraw structure file








144
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxododecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxododecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2109
Shoichi Kusumoto
ERI-29
C69H128N2O22P2 1399.702 Download ChemDraw structure file








145
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxooctanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxooctanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2110
Shoichi Kusumoto
ERI-30
C61H112N2O22P2 1287.490 Download ChemDraw structure file








146
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxohexadecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxohexadecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2111
Shoichi Kusumoto
ERI-31
C77H144N2O22P2 1511.915 Download ChemDraw structure file








147
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)octyl]-6-O-methyl-2-(3-oxododecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxyoctyl]-2-(3-oxododecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2112
Shoichi Kusumoto
ERI-32
C65H120N2O22P2 1343.596 Download ChemDraw structure file








148
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2113
Shoichi Kusumoto
ERI-33
C68H132N2O22P2 1391.723 Download ChemDraw structure file









149
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanyl]-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2114
Shoichi Kusumoto
ERI-34
C68H130N2O24P2 1421.706 Download ChemDraw structure file









150
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2115
Shoichi Kusumoto
ERI-35
C69H132N2O21P2 1387.735 Download ChemDraw structure file









151
N-2' Saturated-acyloxy chain type of lipid A from Rhodobacter sphaeroides
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2116
Shoichi Kusumoto
ERI-36
C74H138N2O24P2 1501.834 Download ChemDraw structure file









152
N-2' trans-Acyloxy chain type of lipid A from Rhodobacter sphaeroides
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-(7-trans-tetradecenoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2117
Shoichi Kusumoto
ERI-37
C74H136N2O24P2 1499.818 Download ChemDraw structure file









153
N-2' cis-d5-C12 Acyloxy chain type of lipid A from Rhodobacter sphaeroides
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-(5-cis-dodecenoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2118
Shoichi Kusumoto
ERI-38
C72H132N2O24P2 1471.765 Download ChemDraw structure file









154
N-2' Hydroxyacyl-(deacyl) type of lipid A from Rhodobacter sphaeroides
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2119
Shoichi Kusumoto
ERI-39
C60H112N2O23P2 1291.478 Download ChemDraw structure file









155
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanyl]-2-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2120
Shoichi Kusumoto
B1060
C68H134N2O21P2 1377.740 Download ChemDraw structure file









156
2-Deoxy-6-O-[2-deoxy-2-[11-cis-octadecenoylamino]-3-O-[(R)-3-methoxydecanoyl]-6-O-methyl-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2121
Shoichi Kusumoto
E5564
C66H124N2O20P2 1327.640 Download ChemDraw structure file









157
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2122
Shoichi Kusumoto
B975
C73H138N2O21P2 1441.825 Download ChemDraw structure file








158
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)undecanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxyundecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2123
Shoichi Kusumoto
B464
C75H140N2O22P2 1483.862 Download ChemDraw structure file








159
6-O-Methyl-O-3 and O-3' alkyl chain type of lipid A from Rhodobacter capsulatus
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(5-cis-dodecenoyloxy)decanyl]-6-O-methyl-2-(3-oxotetradecanoylamino)-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanyl]-2-(3-oxotetradecanoylamino)-a-D-glucopyranose 1,4'-Bisphosphate
CLS2124
Shoichi Kusumoto
E5531
C73H136N2O22P2 1455.809 Download ChemDraw structure file









160
Monophospholyl biosynthetic precursor of lipid A from Escherichia coli
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1-Phosphate
CLS2125
Shoichi Kusumoto
#405, LA-14-HP
C68H129N2O20P 1325.727 Download ChemDraw structure file
Re-LPs binding assay, IL-6-release, TNFa-release; (Ref. 2012)








161
Monophospholyl biosynthetic precursor of lipid A from Escherichia coli
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 4'-Phosphate
CLS2126
Shoichi Kusumoto
#404, LA-14-PH
C68H129N2O20P 1325.727 Download ChemDraw structure file
Re-LPs binding assay, IL-6-release, TNFa-release; (Ref. 2012)








162
Diphosphoryl lipid A from Rhodopseudomonas sphaeroides
2-Deoxy-6-O-[2-deoxy-2-[3-(tetradecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxydecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1-Phosphate
CLS2127
Shoichi Kusumoto
RsLA
C74H139N2O21P 1423.870 Download ChemDraw structure file









163
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-dodecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2128
Shoichi Kusumoto
C66H126N2O21P2 1345.655 Download ChemDraw structure file

1H NMR,31P NMR; (Ref. 2085)
PDM-MS m/z 1344 [(M-H)-]; (Ref. 2085)


Bordetella bronchiseptica




164
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-dodecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2129
Shoichi Kusumoto
C80H152N2O23P2 1572.010 Download ChemDraw structure file

1H NMR,31P NMR; (Ref. 2085)
PDM-MS m/z 1571 [(M-H)-]; (Ref. 2085)


Bordetella bronchiseptica




165
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydodecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2130
Shoichi Kusumoto
C66H126N2O22P2 1361.654 Download ChemDraw structure file

1H NMR,31P NMR; (Ref. 2085)
PDM-MS m/z 1360 [(M-H)-]; (Ref. 2085)


Bordetella bronchiseptica




166
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydodecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2131
Shoichi Kusumoto
C80H152N2O24P2 1588.009 Download ChemDraw structure file

1H NMR,31P NMR; (Ref. 2085)
PDM-MS m/z 1587 [(M-H)-]; (Ref. 2085)


Bordetella bronchiseptica




167
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(hexadecanoyloxy)tetradecanoyl]-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydodecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2132
Shoichi Kusumoto
C96H182N2O25P2 1826.418 Download ChemDraw structure file

1H NMR,31P NMR; (Ref. 2085)
PDM-MS m/z 1825 [(M-H)-]; (Ref. 2085)


Bordetella bronchiseptica




168
2-Deoxy-6-O-[2-deoxy-4-O-[4-deoxyaminoarabinopyranosylphosphoryl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-(hexadecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-(hexadecanoyloxy)tetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1-Arabinofuranosylphosphate
CLS2133
Shoichi Kusumoto
C110H207N3O32P2 2145.769 Download ChemDraw structure file
1H NMR,31P NMR; (Ref. 2086)
PDM-MS m/z 1825 [(M-H)-]; (Ref. 2086)


Yersinia pseudotuberculosis




169
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-(dodecanoyloxy)tetradecanoyl]-2-[(R)-3-(10-hexadecenoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2134
Shoichi Kusumoto
C96H180N2O25P2 1824.402 Download ChemDraw structure file
1H NMR,31P NMR; (Ref. 2086)
PDM-MS m/z 1825 [(M-H)-]; (Ref. 2086)


Yersinia petisis




170
2-Deoxy-6-O-[2-deoxy-4-O-[4-deoxyaminoarabinopyranosylphosphoryl]-3-O-[(R)-3-(dodecanoyloxy)tetradecanoyl]-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose Phosphate
CLS2135
Shoichi Kusumoto
C97H183N3O28P2 1901.442 Download ChemDraw structure file
1H NMR, 31P NMR; (Ref. 2086)
PDM-MS m/z 1825 [(M-H)-]; (Ref. 2086)


Yersinia ruckeri




171
2-Deoxy-6-O-[2-deoxy-4-O-[4-deoxyaminoarabinopyranosylphosphoryl]-3-O-[(R)-3-(dodecanoyloxy)tetradecanoyl]-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose Phosphate
CLS2136
Shoichi Kusumoto
C99H187N3O28P2 1929.495 Download ChemDraw structure file
1H NMR, 31P NMR; (Ref. 2086)
PDM-MS m/z 1927 [(M-H)-]; (Ref. 2086)


Yersinia enterocolitica




172
Lipid A from Enterobacter agglomerans
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-(2-(S)-hydroxytetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-(hexadecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxytetradecanoyl]-b-D-glucopyranose 4'-Phosphate
CLS2137
Shoichi Kusumoto
C110H207N2O24P 1972.793 Download ChemDraw structure file


LDMS, PDMS m/z 1716 [(M-H)-]; (Ref. 2087)


Enterobacter agglomerans




173
Lipid A from Enterobacter agglomerans
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-(3-hydroxytetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-(hexadecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-hydroxytetradecanoyl]-b-D-glucopyranose 4'-Phosphate
CLS2138
Shoichi Kusumoto
C110H207N2O24P 1972.793 Download ChemDraw structure file


LDMS, PDMS m/z 1716 [(M-H)-]; (Ref. 2087)


Enterobacter agglomerans




174
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-(2-(S)-hydroxytetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-hydroxytetradecanoylamino]-3-O-[(R)-3-hydroxytetradecanoyl]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2139
Shoichi Kusumoto
C94H178N2O26P2 1814.365 Download ChemDraw structure file


MALDI-MS m/z 1813.0 [(M-H)-]; (Ref. 2088)


Salmonella typhimurium




175
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-(2-(S)-hydroxytetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-(hexadecanoyloxy)tradecanoylamino]-3-O-[(R)-3-hydroxytetradecanoyl]-a-D-glucopyranose 1,4'-Bisphosphate
CLS2140
Shoichi Kusumoto
C108H204N2O27P2 2024.720 Download ChemDraw structure file


MALDI-MS m/z 2052.4 [(M-H)-]; (Ref. 2088)


Salmonella typhimurium




176
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-hydroxytetradecanoylamino]-3-O-[(R)-3-(dodecanyloxy)tetradecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-(3-(donecanyloxy)tetradecanoyloxy)tradecanoylamino]-b-D-glucopyranose 4'-Phosphate
CLS2141
Shoichi Kusumoto
C92H177N2O20P 1662.365 Download ChemDraw structure file
T-cell proliferation (blastogenesis), interferon-gamma production; (Ref. 2089)
[a]20D -3.5 (c 0.2, chloroform/methanol, 4:1); (Ref. 2089)

ESI-MS m/z 1660.3 [(M-H)-]; (Ref. 2089)

HP-TLC: Rf 0.20 (chloroform/methanol/water/ammmonium hydroxide, 7:3:0.4:0.2); (Ref. 2089)




177
2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanyloxy)tetradecanoylamino]-3-O-[(R)-3-(dodecanyloxy)tetradecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-(3-(donecanyloxy)tetradecanoyloxy)tradecanoylamino]-b-D-glucopyranose 4'-Phosphate
CLS2142
Shoichi Kusumoto
C104H201N2O20P 1830.684 Download ChemDraw structure file
T-cell proliferation (blastogenesis), interferon-gamma production; (Ref. 2089)
[a]20D +2.0 (c 0.2, chloroform/methanol, 4:1); (Ref. 2089)

ESI-MS m/z 1828.5 [(M-H)-]; (Ref. 2089)

HP-TLC: Rf 0.38 (chloroform/methanol/water/ammmonium hydroxide, 7:3:0.4:0.2); (Ref. 2089)




178
Lipid A of Flavobacterium meningosepticum
2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxyhexadecanoyl]-2-[(R)-3-(13-methyltetradecanyloxy)-15-methylhexadecanoyl]-b-D-glucopyranosyl]-2-[(R)-3-hydroxy-15-methylhexadecanoylamino]-3-O-[(R)-3-hydroxy-13-methyltetradecanoyl]-a-D-glucopyranose 1-Phosphate
CLS2143
Shoichi Kusumoto
C92H175N2O21P 1676.349 Download ChemDraw structure file
T-cell proliferation (blastogenesis), interferon-gamma production; (Ref. 2089)
1H NMR, 31P NMR; (Ref. 2090)
EI-MS; (Ref. 2090)


Flavobacterium meningosepticum IFO12535




179
Lipid A of Flavobacterium meningosepticum
2-Deoxy-6-O-[2.3-dideoxy-3-O-[(R)-3-hydroxyhexadecanoyl]-2-[(R)-3-(13-methyltetradecanyloxy)-15-methylhexadecanoylamino]-b-D-glucopyranosyl]-2-[(R)-3-hydroxy-15-methylhexadecanoylamino]-3-O-[(R)-3-hydroxy-13-methyltetradecanoyl]-a-D-glucopyranose 1-Phosphate
CLS2144
Shoichi Kusumoto
C92H176N3O20P 1675.364 Download ChemDraw structure file
T-cell proliferation (blastogenesis), interferon-gamma production; (Ref. 2089)
1H NMR, 31P NMR; (Ref. 2090)
EI-MS m/z 1673 [(M-H)-]; (Ref. 2090)


Flavobacterium meningosepticum IFO12535




180
neutral glycans isolated from the lipopolysaccharides of reference strains for Serratia marcescens serogroups O16 and O20
CLS3001
Shoichi Kusumoto
C12H22O11 342.296 Download ChemDraw structure file

1H, 13C NMR (Ref. 3001)



Serratia marcescens serogroups O16 and O20




181
the lipopolysaccharide antigenic O-chain produced by Actinobacillus pleuropneumoniae serotype 4 (ATCC 33 378)
CLS3002
Shoichi Kusumoto
C26H45NO20 691.630 Download ChemDraw structure file

1H, 13C NMR (Ref. 3002)


Bio gel P-2 (Ref. 3002)
Actinobacillus pleuropneumoniae serotype 4 (ATCC 33 378)




182
the lipopolysaccharide antigenic O-chain produced by Salmonella ohio (O:6, 7)
CLS3003
Shoichi Kusumoto
C38H65NO31 1031.911 Download ChemDraw structure file

1H NMR (Ref. 3003)


sephadex G-50, G-15, GLC-MS (Ref. 3003)
Salmonella ohio




183
An acidic galactoglucomannan from the O3 reference strain (C. D. C. 863-57) of Serratia marcescens
CLS3004
Shoichi Kusumoto
C30H50O27 842.702 Download ChemDraw structure file

13C NMR (Ref. 3004)


sephadex G-50, HPLC (Ref. 3004)
Serratia marcescens




184
A neutral polymer (the putative O10 antigen) isolated from the lipopolysaccharide of Serratia marcescens strain C. D. C. 1287-54 (O10:H8)
CLS3005
Shoichi Kusumoto
C38H67NO28 985.929 Download ChemDraw structure file

1H, 13C NMR (Ref. 3005)


sephadex G-50 (Ref. 3005)
Serratia marcescens strain C. D. C. 1287-54 (O10:H8)




185
an acidic galactoglucomannan from the O15 reference strain (C. D. C. 4523-60) of Serratia marcescens
CLS3006
Shoichi Kusumoto
C30H50O27 842.702 Download ChemDraw structure file

1H, 13C NMR (Ref. 3006)


sephadex G-15 (Ref. 3006)
the O15 reference strain (C. D. C. 4523-60) of Serratia marcescens




186
O-antigenic polysaccharide of Escherichia coli O86, which possesses blood-group B activity
CLS3007
Shoichi Kusumoto
C34H58N2O25 894.823 Download ChemDraw structure file

1H, 13C NMR, COSY, TQF-COSY, NOESY (Ref. 3007)



Escherichia coli O86




187
the lipopolysaccharide core components from Rhizobium leguminosarum biovar Phaseoli CE3 and two of its symbiotic mutants CE109 and CE309
CLS3008
Shoichi Kusumoto
C26H42O24 738.597 Download ChemDraw structure file

1H NMR (Ref. 3008)
FAB-MS (Ref. 3008)

GLC, Bio gel P-2 (Ref. 3008)
Rhizobium leguminosarum BIOVER Phaseoli CE3 and two of its symbiotic mutants CE109 and CE309




188
the lipopolysaccharide core components from Rhizobium leguminosarum biovar Phaseoli CE3 and two of its symbiotic mutants CE109 and CE309
CLS3009
Shoichi Kusumoto
C20H30O20 590.440 Download ChemDraw structure file

1H NMR (Ref. 3009)


GLC, Bio gel P-2 (Ref. 3009)
Rhizobium leguminosarum BIOVER Phaseoli CE3 and two of its symbiotic mutants CE109 and CE309




189
the antigenic lipopolysaccharide O-chains produced by Salmonella urbana and Salmonella godesberg
CLS3010
Shoichi Kusumoto
C34H58N2O24 878.823 Download ChemDraw structure file

1H, 13C NMR, COSY (Ref. 3010)



Salmonella urbana and Salmonella godesberg




190
O-specific side-chains of the Escherichia coli O10 lipopolysaccharide
CLS3011
Shoichi Kusumoto
C34H57N2O27 925.814 Download ChemDraw structure file

1H, 13C NMR (Ref. 3011)



Escherichia coli O10




191
O-specific side-chains of the Escherichia coli O2 lipopolysaccharide
CLS3012
Shoichi Kusumoto
C34H58N2O22 846.825 Download ChemDraw structure file

1H, 13C NMR, COSY, NOESY (Ref. 3012)



Escherichia coli O2




192
O-antigen of Pseudomonas syringae PV. phaseolicola STRAIN NPS 3121
CLS3013
Shoichi Kusumoto
C30H52O21 748.721 Download ChemDraw structure file

1H, 13C NMR (Ref. 3013)



Pseudomonas syringae PV. phaseolicola STRAIN NPS 3121




193
O-antigen of Pseudomonas syringae PV. phaseolicola STRAIN NPS 3121
CLS3014
Shoichi Kusumoto
C30H52O21 748.721 Download ChemDraw structure file

1H, 13C NMR (Ref. 3014)



Pseudomonas syringae PV. phaseolicola STRAIN NPS 3121




194
O-antigen of Pseudomonas syringae PV. phaseolicola STRAIN NPS 3121
CLS3015
Shoichi Kusumoto
C30H52O21 748.721 Download ChemDraw structure file

1H, 13C NMR (Ref. 3015)



Pseudomonas syringae PV. phaseolicola STRAIN NPS 3121




195
an acidic galactorhamnan from the O2 reference strain (C. D. C. 868-57) of Serratia marcescens
CLS3016
Shoichi Kusumoto
C24H42NO18 632.586 Download ChemDraw structure file

1H, 13C NMR (Ref. 3016)



Serratia marcescens




196
O-specific polysaccharide chain from Citrobacter O23-lipopolysaccharide
CLS3017
Shoichi Kusumoto
C26H45NO21 707.630 Download ChemDraw structure file

1H, 13C NMR, COSY (Ref. 3017)



Citrobacter O23




197
an acidic galactomannan from the reference strain for Serratia marcescens serogroup O4
CLS3018
Shoichi Kusumoto
C27H44O23 736.624 Download ChemDraw structure file

1H, 13C NMR (Ref. 3018)



erratia marcescens serogroup O4




198
O-antigen polysaccharide of Haemophilus pleuropneumoniae serotype 3 (ATCC 27090) lipopolysaccharide
CLS3019
Shoichi Kusumoto
C30H52O26 828.718 Download ChemDraw structure file

1H, 13C NMR, COSY (Ref. 3019)


GLC-MS (Ref. 3019)
Haemophilus pleuropneumoniae serotype 3 (ATCC 27090)




199
the major lipopolysaccharide antigenic O-chain produced by Salmonella carrau (O:6, 14, 24)
CLS3020
Shoichi Kusumoto
C32H55NO26 869.770 Download ChemDraw structure file

1H, 13C NMR, COSY (Ref. 3020)


Biogel P-2 (Ref. 3020)
Salmonella carrau (O:6, 14, 24)




200
O-specific polysaccharide chain of the Shigella dysenteriae type 7 lipopolysaccharide
CLS3021
Shoichi Kusumoto
C36H56N6O23 940.856 Download ChemDraw structure file

1H, 13C NMR (Ref. 3021)



Shigella dysenteriae type 7




201
lipopolysaccharides of reference strains for Serratia marcescens serogroups O4 and O7, and of an O14 strain
CLS3022
Shoichi Kusumoto
C14H24O11 368.334 Download ChemDraw structure file

1H, 13C NMR (Ref. 3022)



Serratia marcescens serogroups O4 and O7, and of an O14 strain




202
lipopolysaccharides from two strains of Serratia marcescens O13: structure of the putative O13 antigen
CLS3023
Shoichi Kusumoto
C38H63NO32 1045.894 Download ChemDraw structure file

1H, 13C NMR (Ref. 3023)



(C. D. C. 3607-60 and IP 421) of Serratia marcescens O13




203
the lipopolysaccharides of Serratia marcescens O6 (strain C. D. C. 862-57)
CLS3024
Shoichi Kusumoto
C13H23NO10 353.322 Download ChemDraw structure file

1H, 13C NMR (Ref. 3024)


GLC-MS (Ref. 3024)
Serratia marcescens O6 (strain C. D. C. 862-57) and O12 (C. D. C. 6320-58)




204
the lipopolysaccharides of Serratia marcescens O12 (C. D. C. 6320-58)
CLS3025
Shoichi Kusumoto
C12H22O10 326.297 Download ChemDraw structure file

1H, 13C NMR (Ref. 3025)


GLC-MS (Ref. 3025)
Serratia marcescens O6 (strain C. D. C. 862-57) and O12 (C. D. C. 6320-58)




205
lipopolysaccharide of Serratia marcescens O1 (strain C. D. C. 866-57)
CLS3026
Shoichi Kusumoto
C12H22O10 326.297 Download ChemDraw structure file

1H, 13C NMR (Ref. 3026)


GLC-MS (Ref. 3026)
Serratia marcescens O1 (strain C. D. C. 866-57)




206
the lipopolysaccharide of Serratia marcescens C. D. C. 1783-57 (O14 : H9)
CLS3027
Shoichi Kusumoto
C28H48N2O21 748.682 Download ChemDraw structure file

1H, 13C NMR (Ref. 3027)


GLC, GLC-MS, sephadex G-10, G-50 (Ref. 3027)
Serratia marcescens C. D. C. 1783-57 (O14 : H9)




207
the O-specific side chain of the lipopolysaccharide from Escherichia coli O:7
CLS3028
Shoichi Kusumoto
C34H58N2O24 878.823 Download ChemDraw structure file

1H, 13C NMR (Ref. 3028)


sephadex G-15, G-50 (Ref. 3028)
Escherichia coli O:7




208
O-antigen of the lipopolysaccharide from an avirulent strain (M4S) of Pseudomonas solanacearum
CLS3029
Shoichi Kusumoto
C26H45NO18 659.631 Download ChemDraw structure file

1H, 13C NMR (Ref. 3029)


sephadex G-15, G-50 (Ref. 3029)
(M4S) of Pseudomonas solanacearum




209
polysaccharide chain of Shigella boydii type 2 lipopolysaccharide
CLS3030
Shoichi Kusumoto
C37H60NO29 982.862 Download ChemDraw structure file

1H, 13C NMR (Ref. 3030)


sephadex G-15, G-50, GLC-MS (Ref. 3030)
Shigella boydii type 2




210
Lipopolysaccharide from the O14 type strain of Serratia marcescens
CLS3031
Shoichi Kusumoto
C13H23O10 339.316 Download ChemDraw structure file

1H, 13C NMR (Ref. 3031)


sephadex G-50, GLC-MS (Ref. 3031)
O14 type strain of Serratia marcescens




211
the core oligosaccharide of Aeromonas hydrophila (chemotype
CLS3032
Shoichi Kusumoto
C40H71NO34 1109.978 Download ChemDraw structure file

1H, 13C NMR (Ref. 3032)


sephadex G-15, LH-20, GLC-MS (Ref. 3032)
Aeromonas hydrophila (CHEMOTYPE




212
Lipopolysaccharides from Pseudomonas maltophilia
CLS3033
Shoichi Kusumoto
C19H33NO14 499.464 Download ChemDraw structure file

1H, 13C NMR (Ref. 3033)


sephadex G-50, GLC-MS (Ref. 3033)
Pseudomonas maltophilia




213
he O-antigens from Salmonella greenside and Salmonella adelaide
CLS3034
Shoichi Kusumoto
C32H55NO24 837.771 Download ChemDraw structure file

1H, 13C NMR (Ref. 3034)


sephadex G-25, Biogel P-2 (Ref. 3034)
Salmonella greenside and Salmonella adelaide




214
an R-type oligosaccharide core obtained from some lipopolysaccharides of Neisseria meningitidis
CLS3035
Shoichi Kusumoto
C56H94N2O45 1515.332 Download ChemDraw structure file

1H, 13C NMR (Ref. 3035)


sephadex G-25, LH-20, GLC-MS (Ref. 3035)
Neisseria meningitidis




215
a carbohydrate chain isolated from the lipopolysaccharide of Shigella boydii type 8
CLS3036
Shoichi Kusumoto
C34H58N2O26 910.822 Download ChemDraw structure file




sephadex G-100, G-25 (Ref. 3036)
Shigella boydii type 8




216
the core oligosaccharide of Aeromonas hydrophila (chemotype III) lipopolysaccharide
CLS3037
Shoichi Kusumoto
C40H69NO33 1091.963 Download ChemDraw structure file

1H, 13C NMR (Ref. 3037)


sephadex G-15 (Ref. 3037)
Aeromonas hydrophila (chemotype III)




217
O-specific side-chain of the lipopolysaccharide from Escherichia coli O 55
CLS3038
Shoichi Kusumoto
C34H58N2O25 894.823 Download ChemDraw structure file

1H NMR (Ref. 3038)


sephadex G-15, Biogel P-2 (Ref. 3038)
Escherichia coli O 55




218
an acetylated mannan from Pseudomonas diminuta N. C. T. C. 8545
CLS3039
Shoichi Kusumoto
C14H24O12 384.333 Download ChemDraw structure file

1H, 13C NMR (Ref. 3039)


GLC-MS, sephadex G-10, 15, 50, 100 (Ref. 3039)
Pseudomonas diminuta N. C. T. C. 8545




219
the O-specific side-chains of the lipopolysaccharide from Yersinia enterocolitica Ye 128
CLS3040
Shoichi Kusumoto
C8H16O5 192.210 Download ChemDraw structure file

1H, 13C NMR (Ref. 3040)


GLC-MS (Ref. 3040)
Yersinia enterocolitica Ye 128




220
the O-antigen of Vibrio cholera, inaba 569 B
CLS3041
Shoichi Kusumoto
C12H20O12 356.280 Download ChemDraw structure file




GLC (Ref. 3041)
Vibrio cholera, inaba 569 B




221
the O-antigen of Vibrio cholera, inaba 569 B
CLS3042
Shoichi Kusumoto
C13H22O13 386.306 Download ChemDraw structure file




GLC (Ref. 3042)
Vibrio cholera, inaba 569 B




222
the O-antigen of Vibrio cholera, inaba 569 B
CLS3043
Shoichi Kusumoto
C13H24O12 372.322 Download ChemDraw structure file




GLC (Ref. 3043)
Vibrio cholera, inaba 569 B




223
the O-antigen of Vibrio cholera, inaba 569 B
CLS3044
Shoichi Kusumoto
C14H28O12 388.365 Download ChemDraw structure file




GLC (Ref. 3044)
Vibrio cholera, inaba 569 B




224
the O-antigen of Vibrio cholera, inaba 569 B
CLS3045
Shoichi Kusumoto
C21H37NO17 575.515 Download ChemDraw structure file




GLC (Ref. 3045)
Vibrio cholera, inaba 569 B




225
the acidic arabinomannan of Mycobacterium smegmatis
CLS3046
Shoichi Kusumoto
CH35H57O29 568.724 Download ChemDraw structure file

1H, 13C NMR (Ref. 3046)


DEAE-sephadex A-25 (Ref. 3046)
Mycobacterium smegmatis




226
the acidic arabinomannan of Mycobacterium smegmatis
CLS3047
Shoichi Kusumoto
C35H57O29 941.810 Download ChemDraw structure file

1H, 13C NMR (Ref. 3047)


DEAE-sephadex A-25 (Ref. 3047)
Mycobacterium smegmatis




227
Lipopolysaccharides from Pseudomonas maltophilia: structural studies of the side-chain polysaccharide from strain N. C. T. C. 10257
CLS3048
Shoichi Kusumoto
C24H42O17 602.580 Download ChemDraw structure file

1H, 13C NMR (Ref. 3048)


sephadex G-75, 50, 15, 10, GLC-MS (Ref. 3048)
Pseudomonas maltophilia




228
he hexose region of the enterobacteriaceae type R3 core polysaccharide
CLS3049
Shoichi Kusumoto
C32H55NO26 869.770 Download ChemDraw structure file





enterobacteriaceae type R3




229
the O-antigen of Vibrio cholera OGAWA G-2102
CLS3050
Shoichi Kusumoto
Download ChemDraw structure file




GLC (Ref. 3050)
Vibrio cholera OGAWA G-2102




230
the O-specific polysaccharide chain of Shigella dysenteriae type 3 lipopolysaccharide
CLS3051
Shoichi Kusumoto
C35H57O27 909.811 Download ChemDraw structure file





Shigella dysenteriae type 3




231
the Klebsiella O group 12 lipopolysaccharide
CLS3052
Shoichi Kusumoto
C14H25NO10 367.349 Download ChemDraw structure file

1H NMR (Ref. 3052)


sephadex G-15 (Ref. 3052)
Klebsiella O group 12




232
the hexose region of the lipopolysaccharide from Escherichia coli C
CLS3053
Shoichi Kusumoto
C30H52O26 828.718 Download ChemDraw structure file




sephadex G-25 (Ref. 3053)
Escherichia coli C




233
a new acidic sugar from Shigella dysenteriae type 3 lipopolysaccharide
CLS3054
Shoichi Kusumoto
C9H16O8 252.219 Download ChemDraw structure file

1H, 13C NMR (Ref. 3054)


sephadex G-50 (Ref. 3054)
Shigella dysenteriae type 3




234
he O-specific side-chains of the cell-wall lipopolysaccharide from Escherichia coli O 69
CLS3055
Shoichi Kusumoto
C26H45NO19 675.631 Download ChemDraw structure file

1H NMR (Ref. 3055)


sephadex G-50, 25 (Ref. 3055)
Escherichia coli O 69




235
antigenic lipopolysaccharides of bacteria
CLS3056
Shoichi Kusumoto
C9H15O6 219.212 Download ChemDraw structure file




sephadex G-50
Shigella dysenteriae type 5




236
the O-specific polysaccharide chain of Shigella boydii 6 lipopolysaccharide
CLS3057
Shoichi Kusumoto
C32H53NO27 883.754 Download ChemDraw structure file





Shigella boydii 6




237
O-specific side-chains of the cell-wall lipopolysaccharide from Escherichia coli O 75
CLS3058
Shoichi Kusumoto
C26H45NO20 691.630 Download ChemDraw structure file




sephadex G-25 (Ref. 3058)
Escherichia coli O 75




238
the O-specific side-chains of the cell-wall lipopolysaccharide from Salmonella muenster
CLS3059
Shoichi Kusumoto
C24H42O20 650.578 Download ChemDraw structure file




GLC, sephadex G-15 (Ref. 3059)
Salmonella muenster




239
the O-specific side-chains of the cell-wall lipopolysaccharides from Salmonella newport and Salmonella kentucky
CLS3060
Shoichi Kusumoto
C24H42O20 650.578 Download ChemDraw structure file





Salmonella senftenberg




240
the O-specific side-chains of the cell-wall lipopolysaccharides from Salmonella newport and Salmonella kentucky
CLS3061
Shoichi Kusumoto
Download ChemDraw structure file




GLC-MS (Ref. 3061)
Salmonella newport and Salmonella kentucky




241
the O-specific side-chains of the cell-wall lipopolysaccharides from Salmonella newport and Salmonella kentucky
CLS3062
Shoichi Kusumoto
Download ChemDraw structure file




GLC-MS (Ref. 3062)
Salmonella newport and Salmonella kentucky




242
the O-specific side-chains of the cell-wall lipopolysaccharides from Salmonella newport and Salmonella kentucky
CLS3063
Shoichi Kusumoto
Download ChemDraw structure file




GLC-MS (Ref. 3063)
Salmonella newport and Salmonella kentucky




243
the heptose/3-deoxy-D-manno-2-octulosonic acid region (inner core) of the lipopolysaccharide from Salmonella minnesota rough mutants
CLS3064
Shoichi Kusumoto
C32H46O29 894.690 Download ChemDraw structure file


EI-MS (Ref. 3064)


Salmonella minnesota




244
the Pasteurella haemolytica serotype T10 lipopolysaccharide O-antigen by N.M.R. spectroscopy
CLS3065
Shoichi Kusumoto
C12H22O11 342.296 Download ChemDraw structure file

1H, 13C NMR:COSY (Ref. 3065)


sephadex G-50 (Ref. 3065)
Pasteurella haemolytica serotype T10




245
Lipopolysaccharide of in Rhizobium etli and mutants
CLS4501
Shoichi Kusumoto
C34H54O31 958.774 Download ChemDraw structure file


FAB-MS, ES-MS; (Ref. 4501)

Gel-filtration chromatography: Sephadex G-50; (Ref. 4501)
Rhizobium etli and mutants




246
Lipopolysaccharide of in Rhizobium etli and mutants
CLS4502
Shoichi Kusumoto
C20H30O20 590.440 Download ChemDraw structure file


FAB-MS, ES-MS; (Ref. 4501)

Gel-filtration chromatography: Sephadex G-50; (Ref. 4501)
Rhizobium etli and mutants




247
O-specific chain of Hafnia alvei strain 1192 lipopolysaccharide
CLS4503
Shoichi Kusumoto
C37H61NO28 967.870 Download ChemDraw structure file

1H NMR, 13C NMR: dq-COSY, delayed COSY, double relayed COSY, TOCSY, NOESY, HMQC; (Ref. 4503)
MALDI-TOF-MS, ES-MS; (Ref. 4503)

Bio-Gel P-10, Bio-Gel P-2; (Ref. 4503)
Hafnia alvei strain 1192




248
Core polysaccharide of Hafnia alvei strain 1192 lipopolysaccharide
CLS4504
Shoichi Kusumoto
C43H78NO45P3 1421.980 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: dq-COSY, delayed COSY, double relayed COSY, TOCSY, NOESY, HMQC; (Ref. 4503)
MALDI-TOF-MS, ES-MS; (Ref. 4503)

Bio-Gel P-10, Bio-Gel P-2; (Ref. 4503)
Hafnia alvei strain 1192




249
O-specific polysaccharide from Thiobacillus sp. IFO 14570
CLS4505
Shoichi Kusumoto
C30H46N6O17 762.716 Download ChemDraw structure file

1H NMR, 13C NMR: 2D COSY, (RCT)COSY, ROESY; (Ref. 4505)


Sephadex G-50; (Ref. 4505)
Thiobacillus sp. IFO 14570




250
Oligosaccharide bisphosphates isolated from the lipopolysaccharide of a recombinant Escherichia coli strain expressing the gene gseA of Chlamydia psittaci 6BC
CLS4506
Shoichi Kusumoto
compound 3
C36H62N2O36P2 1160.817 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: 2D COSY(H-H and H-P), NOESY, HMQC; (Ref. 4506)


Affinity chromatography, Gel-permeation chromatography; (Ref. 4506)
recombinant Escherichia coli strain expressing the gene gseA [3-deoxy-D-manno-octulopyranosonic acid (Kdo) transferase] of Chlamydia psittaci 6BC




251
Oligosaccharide bisphosphates isolated from the lipopolysaccharide of a recombinant Escherichia coli strain expressing the gene gseA of Chlamydia psittaci 6BC
CLS4507
Shoichi Kusumoto
compound 4 (hexasaccharide bisphosphate)
C44H74N2O43P2 1380.994 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: 2D COSY(H-H and H-P), NOESY, HMQC; (Ref. 4506)


Affinity chromatography, Gel-permeation chromatography; (Ref. 4506)
recombinant Escherichia coli strain expressing the gene gseA [3-deoxy-D-manno-octulopyranosonic acid (Kdo) transferase] of Chlamydia psittaci 6BC




252
O-specific polysaccharide of Proteus mirabilis O28
CLS4508
Shoichi Kusumoto
C37H60N4O27 992.883 Download ChemDraw structure file

1H NMR, 13C NMR: 2D COSY, TOCSY, ROESY, HMQC; (Ref. 4507)


Sephadex G-50: pyridine/Acetic acid pH 4.5; (Ref. 4507)
Proteus mirabilis O28




253
O-specific polysaccharide of Proteus penneri strain 12 (ATCC 33519)
CLS4509
Shoichi Kusumoto
C36H57N3O25 931.843 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, heteronuclear COSY, NOE, HMQC; (Ref. 4509)


Gel chromatography: Sephadex G-50; (Ref. 4509)
Proteus penneri strain 12 (ATCC 33519)




254
O-specific polysaccharides of Escherichia coli O56
CLS4510
Shoichi Kusumoto
C31H52N2O24 836.744 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, COSYRCT, C-H COSY, NOE, ROESY; (Ref. 4510)


repeated GPC; (Ref. 4510)
Escherichia coli O56




255
O-specific polysaccharides of Escherichia coli O24
CLS4511
Shoichi Kusumoto
C31H52N2O24 836.744 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, COSYRCT, C-H COSY, NOE, ROESY; (Ref. 4510)


repeated GPC; (Ref. 4510)
Escherichia coli O24




256
Saccharide part of the cell envelope lipooligosaccharide from Haemophilus influenzae strain galEgalK
CLS4512
Shoichi Kusumoto
C55H96NO49P 1586.302 Download ChemDraw structure file

1H NMR, 13C NMR: DQF-COSY, HOHAHA, NOESY, HMQC; (Ref. 4512)
FAB-MS; (Ref. 4512)

Gel-permeation chromatography: Bio-Gel P4; (Ref. 4512)
Haemophilus influenzae strain galEgalK




257
Saccharide part of the cell envelope lipooligosaccharide from Haemophilus influenzae strain galEgalK
CLS4513
Shoichi Kusumoto
C49H86NO44P 1424.161 Download ChemDraw structure file

1H NMR, 13C NMR: DQF-COSY, HOHAHA, NOESY, HMQC; (Ref. 4512)
FAB-MS; (Ref. 4512)

Gel-permeation chromatography: Bio-Gel P4; (Ref. 4512)
Haemophilus influenzae strain galEgalK




258
Saccharide part of the cell envelope lipooligosaccharide from Haemophilus influenzae strain galEgalK
CLS4514
Shoichi Kusumoto
C43H76NO39P 1262.021 Download ChemDraw structure file

1H NMR, 13C NMR: DQF-COSY, HOHAHA, NOESY, HMQC; (Ref. 4512)
FAB-MS; (Ref. 4512)

Gel-permeation chromatography: Bio-Gel P4; (Ref. 4512)
Haemophilus influenzae strain galEgalK




259
O6 antigen of Stenotrophomonas (Xanthomonas or Pseudomonas) maltophilia
CLS4515
Shoichi Kusumoto
C19H33NO14 499.464 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, HMQC; (Ref. 4515)


Gel chromatography: Sephadex G-50; (Ref. 4515)
Stenotrophomonas (Xanthomonas or Pseudomonas) maltophilia




260
O antigen from Burkholderia cepacia serotype E (O2)
CLS4516
Shoichi Kusumoto
C18H32O16 504.437 Download ChemDraw structure file

[a]D +47
1H NMR, 13C NMR: COSY, NOESY, HMQC; (Ref. 4516)
GLC-EI-MS, FAB-MS; (Ref. 4516)

Gel-filtration chromatography: Sephadex G-50; (Ref. 4516)
Burkholderia cepacia serotype E (O2)




261
O antigen from Burkholderia cepacia serotype E (O2)
CLS4517
Shoichi Kusumoto
C18H32O16 504.437 Download ChemDraw structure file

[a]D +47
1H NMR, 13C NMR: COSY, NOESY, HMQC; (Ref. 4516)
GLC-EI-MS, FAB-MS; (Ref. 4516)

Gel-filtration chromatography: Sephadex G-50; (Ref. 4516)
Burkholderia cepacia serotype E (O2)




262
O-specific polysaccharide of Hafnia alvei 1204
CLS4518
Shoichi Kusumoto
C41H67N3O31 1097.972 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, TOCSY, ROESY; (Ref. 4518)
GLC-MS; (Ref. 4518)

Gel-permeation chromatography: Sephadex G-50; (Ref. 4518)
O-specific polysaccharide of Hafnia alvei 1204




263
Core region of Campylobacter jejuni O:3 lipopolysaccharide
CLS4519
Shoichi Kusumoto
C66H112N4O55P2 1903.537 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: COSY, NOESY, RCT-COSY, HMBC; (Ref. 4519)
FAB-MS; (Ref. 4519)

Gel-permeation chromatography: Bio-Gel P6; (Ref. 4519)
Campylobacter jejuni O:3




264
Associated polysaccharide of Campylobacter jejuni O:3
CLS4520
Shoichi Kusumoto
C13H24O12 372.322 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, NOESY, RCT-COSY, HMBC; (Ref. 4519)
FAB-MS; (Ref. 4519)

Gel-permeation chromatography: Bio-Gel P6; (Ref. 4519)
Campylobacter jejuni O:3




265
Lipopolysaccharide of Burkholderia (Pseudomonas) cepacia serogroup O4
CLS4521
Shoichi Kusumoto
C20H35NO16 545.489 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, NOESY, HMQC; (Ref. 4520)


Sephadex G-50; (Ref. 4520)
Burkholderia (Pseudomonas) cepacia serogroup O4




266
Lipopolysaccharide of Burkholderia (Pseudomonas) cepacia serogroup O4
CLS4522
Shoichi Kusumoto
C22H38N2O15 570.542 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, NOESY, HMQC; (Ref. 4521)


Sephadex G-50; (Ref. 4521)
Burkholderia (Pseudomonas) cepacia serogroup O4




267
O-antigen lipopolysaccharide from two strains of Plesiomonas shigelloides
CLS4523
Shoichi Kusumoto
C32H53NO24 835.756 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, C-H COSY, NOESY, HMQC, HMBC; (Ref. 4523)



Plesiomonas shigelloides strain 22074, 12254




268
Lipopolysaccharides from Serratia marcescens O26
CLS4524
Shoichi Kusumoto
C14H25NO10 367.349 Download ChemDraw structure file
ELISA antiserum; (Ref. 4524)
1H NMR, 13C NMR; (Ref. 4524)


Sephadex G-50; (Ref. 4524)
Serratia marcescens serotypes O26




269
Lipopolysaccharides from Serratia marcescens O26
CLS4525
Shoichi Kusumoto
C14H25NO10 367.349 Download ChemDraw structure file
ELISA antiserum; (Ref. 4524)
1H NMR, 13C NMR; (Ref. 4524)


Sephadex G-50; (Ref. 4524)
Serratia marcescens serotypes O26




270
O-specific polysaccharide chain of Proteus penneri strain 42
CLS4526
Shoichi Kusumoto
C26H43NO22 721.613 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, COSYRCT, NOE, XHCORRD; (Ref. 4526)


Gel-permeation chromatography: Sephadex G-50, pyridine acetate buffer (pH 4.5); (Ref. 4526)
Proteus penneri strain 42




271
Capsular polysaccharide of Vibrio cholerae O139 synonym Bengal
CLS4527
Shoichi Kusumoto
C40H65N2O29P 1068.914 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: COSY, relayed COSY, TOCSY, ROESY, HMQC, H-P HMQC; (Ref. 4527)


Gel-permeation chromatography: Sephadex G-50; (Ref. 4527)
Vibrio cholerae O139 synonym Bengal




272
Proteus mirabilis O43 O antigen
CLS4528
Shoichi Kusumoto
C26H41NO23 735.597 Download ChemDraw structure file
The reaction with rabbit anti-O serum; (Ref. 4528)
1H NMR, 13C NMR: COSY, C-H COSY, NOE; (Ref. 4528)


Gel-permeation chromatography: Sephadex G-50, 0.05 M pyridine acetate, pH 4.5; (Ref. 4528)
Proteus mirabilis O43




273
O-specific polysaccharide chains of Pectinatus frisingensis
CLS4529
Shoichi Kusumoto
C24H42O17 602.580 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, NOE, ROESY, C-H COSY; (Ref. 4529)


Gel-permeation chromatography: Sephadex G-50 or TSK HW-40, 0.5 M pyridine acetate, pH 4.5, Anion-exchange chromatography: Durrum DAX4, 0.5 M sodium borate, pH 9; (Ref. 4529)
Pectinatus frisingensis




274
O-specific polysaccharide chains of Pectinatus cerevisiiphilus
CLS4530
Shoichi Kusumoto
C12H22O10 326.297 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, NOE, ROESY, C-H COSY; (Ref. 4529)


Gel-permeation chromatography: Sephadex G-50 or TSK HW-40, 0.5 M pyridine acetate, pH 4.5, Anion-exchange chromatography: Durrum DAX4, 0.5 M sodium borate, pH 9; (Ref. 4529)
Pectinatus cerevisiiphilus




275
O antigen of Burkholderia pseudomallei
CLS4531
Shoichi Kusumoto
O-PS I
C9H16O7 236.219 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, HMQC, HMBC; (Ref. 4531)
GLC-MS; (Ref. 4531)

Gel-filtration chromatography: Sephadex G-50, 0.05 M pyridinium acetate, pH 4.6; (Ref. 4531)
Burkholderia pseudomallei




276
O antigen of Burkholderia pseudomallei
CLS4532
Shoichi Kusumoto
O-PS II
C12H22O10 326.297 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, HMQC, HMBC; (Ref. 4531)
GLC-MS; (Ref. 4531)

Gel-filtration chromatography: Sephadex G-50, 0.05 M pyridinium acetate, pH 4.6; (Ref. 4531)
Burkholderia pseudomallei




277
Lipooligosaccharide from Haemophilus ducreyi ITM 5535, ITM 3147, and a fresh clinical isolate, ACY1
CLS4533
Shoichi Kusumoto
C74H127N3O60 2018.784 Download ChemDraw structure file

1H NMR, 13C NMR; (Ref. 4533)
FAB-MS, ESI-MS; (Ref. 4533)

Gel-permeation chromatography: Bio-Gel P-4, 0.1 mM pyridinium acetate, pH 5; (Ref. 4533)
Haemophilus ducreyi ITM 5535, ITM 3147, and a fresh clinical isolate, ACY1




278
Lipooligosaccharide from Haemophilus ducreyi ITM 5535, ITM 3147, and a fresh clinical isolate, ACY1
CLS4534
Shoichi Kusumoto
C88H150N4O70 2384.118 Download ChemDraw structure file

1H NMR, 13C NMR; (Ref. 4533)
FAB-MS, ESI-MS; (Ref. 4533)

Gel-permeation chromatography: Bio-Gel P-4, 0.1 mM pyridinium acetate, pH 5; (Ref. 4533)
Haemophilus ducreyi ITM 5535, ITM 3147, and a fresh clinical isolate, ACY1




279
Lipooligosaccharide from Haemophilus ducreyi ITM 5535
CLS4535
Shoichi Kusumoto
C85H144N4O68 2310.039 Download ChemDraw structure file

1H NMR, 13C NMR; (Ref. 4533)
FAB-MS, ESI-MS; (Ref. 4533)

Gel-permeation chromatography: Bio-Gel P-4, 0.1 mM pyridinium acetate, pH 5; (Ref. 4533)
Haemophilus ducreyi ITM 5535




280
O-antigen of the lipopolysaccharide of Rhizobium tropici CIAT899
CLS4536
Shoichi Kusumoto
C85H144N4O68 2310.039 Download ChemDraw structure file

1H NMR, 13C NMR: DQF-COSY, HMQC, TOCSY, NOESY, ROESY; (Ref. 4536)


Sephacryl S-500, 0.05 M EDTA-TEA, pH 7.0, Gel-permeation chromatography: Bio-Gel P-2, 1% AcOH; (Ref. 4536)
Rhizobium tropici CIAT899




281
Lipid A-core region of the lipopolysaccharides from Vibrio cholerae O1 smooth strain 569B (Inaba) and rough mutant strain 95R (Ogawa)
CLS4537
Shoichi Kusumoto
C74H130N3O69P3 2258.724 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, HMQC, TOCSY, NOESY; (Ref. 4537)


Sephadex G-50, pyridine acetate; (Ref. 4537)
Vibrio cholerae O1 smooth strain 569B (Inaba) and rough mutant strain 95R (Ogawa)




282
Lipid A-core region of the lipopolysaccharides from Vibrio cholerae O1 smooth strain 569B (Inaba) and rough mutant strain 95R (Ogawa)
CLS4538
Shoichi Kusumoto
C67H118N3O63P3 2066.558 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, HMQC, TOCSY, NOESY; (Ref. 4537)


Sephadex G-50, pyridine acetate; (Ref. 4537)
Vibrio cholerae O1 smooth strain 569B (Inaba) and rough mutant strain 95R (Ogawa)




283
O-antigenic polysaccharide from Escherichia coli O44:H18
CLS4539
Shoichi Kusumoto
C32H55NO26 869.770 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, long-range COSY, relayed COSY, double relayed COSY, C-H COSY, HMBC, NOESY; (Ref. 4539)


Gel-permeation chromatography: Sephadex G-50, 1% pyridine, 0.4% acetic acid; (Ref. 4539)
Escherichia coli O44:H18




284
O-specific polysaccharide of Acinetobacter baumannii O2
CLS4540
Shoichi Kusumoto
C46H78N4O31 1183.120 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, TOCSY, HMQC, NOESY; (Ref. 4540)
GLC-MS; (Ref. 4540)

Gel-permeation chromatography: Sephadex G-50, pyridine/acetic acid, pH 5.4; (Ref. 4540)
Acinetobacter baumannii O2




285
Hafnia alvei strain PCM 1188 O-specific polysaccharide
CLS4541
Shoichi Kusumoto
C34H55NO27 909.791 Download ChemDraw structure file

1H NMR, 13C NMR; (Ref. 4541)
GLC-MS, FAB-MS; (Ref. 4541)

Gel-filtration chromatography: Bio-Gel P-4, 0.05 M pyridinium acetate buffer, pH 5.6; (Ref. 4541)
Hafnia alvei strain PCM 1188




286
O-specific side chain of the Escherichia coli O128 lipopolysaccharide
CLS4542
Shoichi Kusumoto
C34H58N2O25 894.823 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, NOE; (Ref. 4542)
GLC-MS; (Ref. 4542)

Gel-permeation chromatography: Sephadex G-50; (Ref. 4542)
Escherichia coli O128




287
Polysaccharide of Escherichia coli O45
CLS4543
Shoichi Kusumoto
C22H37NO15 555.527 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, COSYRCT, NOE; (Ref. 4543)


Gel-permeation chromatography: Sephadex G-50; (Ref. 4543)
Escherichia coli O45




288
Polysaccharide of Escherichia coli O45-related
CLS4544
Shoichi Kusumoto
C22H37NO16 571.526 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, COSYRCT, NOE; (Ref. 4543)


Gel-permeation chromatography: Sephadex G-50; (Ref. 4543)
Escherichia coli O45-related




289
Polysaccharide of Escherichia coli O66
CLS4545
Shoichi Kusumoto
C36H60N2O26 936.859 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, COSYRCT, NOE; (Ref. 4543)


Gel-permeation chromatography: Sephadex G-50; (Ref. 4543)
Escherichia coli O66




290
O-specific polysaccharide chain of Shigella boydii type 5
CLS4546
Shoichi Kusumoto
C40H65NO32 1071.932 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, NOE, ROESY; (Ref. 4546)


Gel-permeation chromatography: Sephadex G-50; (Ref. 4546)
Shigella boydii type 5




291
Decasaccharide tetraphosphates of O-deacylated lipopolysaccharide of Pseudomonas fluorescens strain ATCC 49271
CLS4547
Shoichi Kusumoto
C66H118N4O65P4 2131.526 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: COSY, ROESY, H-C COSY, H-P COSY; (Ref. 4547)


Gel-permeation chromatography: Sephadex G-50, pyridine acetate buffer (pH 4.5), Anion-exchange HPLC; (Ref. 4547)
Pseudomonas fluorescens strain ATCC 49271




292
Tridecasaccharide tetraphosphates of O-deacylated lipopolysaccharide of Pseudomonas fluorescens strain ATCC 49271
CLS4548
Shoichi Kusumoto
C87H155N7O77P4 2655.058 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: COSY, ROESY, H-C COSY, H-P COSY; (Ref. 4547)


Gel-permeation chromatography: Sephadex G-50, pyridine acetate buffer (pH 4.5), Anion-exchange HPLC; (Ref. 4547)
Pseudomonas fluorescens strain ATCC 49271




293
Oligosaccharide of Campylobacter lari strain PC 637
CLS4549
Shoichi Kusumoto
C74H124N2O60 2001.754 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: COSY, COSYRCT, TOCSY, HMQC, H-P HMBC; (Ref. 4549)
FAB-MS; (Ref. 4549)

Gel-permeation chromatography: Bio-Gel P-2; (Ref. 4549)
Campylobacter lari strain PC 637




294
Extracellular polysaccharide of Campylobacter lari strain PC 637
CLS4550
Shoichi Kusumoto
C27H49O24P 788.637 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: COSY, COSYRCT, TOCSY, HMQC, H-P HMBC; (Ref. 4549)
FAB-MS; (Ref. 4549)

Gel-permeation chromatography: Bio-Gel P-2; (Ref. 4549)
Campylobacter lari strain PC 637




295
Liberated oligosaccharide of the Campylobacter lari type strain ATCC 35221
CLS4551
Shoichi Kusumoto
C72H122N3O60P 2020.697 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: COSY, COSYRCT, TOCSY, NOESY, HMQC, H-P HMBC; (Ref. 4551)
FAB-MS; (Ref. 4551)

Gel-permeation chromatography: Bio-Gel P-2; (Ref. 4551)
Campylobacter lari type strain ATCC 35221




296
Extracellular polysaccharide of Campylobacter lari type strain ATCC 35221
CLS4552
Shoichi Kusumoto
C27H48O22P 755.631 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: COSY, COSYRCT, TOCSY, HMQC, HMQC-TOCSY, H-P HMBC; (Ref. 4551)
FAB-MS; (Ref. 4551)

Gel-permeation chromatography: Bio-Gel P-6; (Ref. 4551)
Campylobacter lari type strain ATCC 35221




297
O-specific polysaccharide chain of Citrobacter freundii O28,1c
CLS4553
Shoichi Kusumoto
C17H30O13 442.412 Download ChemDraw structure file

1H NMR, 13C NMR: NOE, COSY, XHCORRD; (Ref. 4553)


Gel-permeation chromatography: Sephadex G-50, pyridine acetate buffer (pH 4.5); (Ref. 4553)
Citrobacter freundii O28,1c




298
Lipopolysaccharide core region of the O-chain-deficient mutant strain A28 from Pseudomonas aeruginosa serotype 06
CLS4554
Shoichi Kusumoto
C76H131N5O66P2 2232.795 Download ChemDraw structure file

1H NMR, 13C NMR: NOESY, COSY, HMQC; (Ref. 4554)
ES-MS; (Ref. 4554)


Pseudomonas aeruginosa serotype 06




299
Lipopolysaccharide of the Helicobacter pylori type strain NCTC 11637 (ATCC 43504)
CLS4601
Shoichi Kusumoto
C108H182N3O88P 2961.542 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: COSY, TOCSY, HMQC; (Ref. 4601)
FAB-MS; (Ref. 4601)

Gel-permeation chromatography: Bio-Gel P-6; (Ref. 4601)
Helicobacter pylori type strain NCTC 11637 (ATCC 43504)




300
Lipopolysaccharide of the Helicobacter pylori type strain P466
CLS4602
Shoichi Kusumoto
C154H258N5O120P 4130.632 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: NOESY, ROESY, HMBC; (Ref. 4602)
FAB-MS; (Ref. 4602)

Gel-permeation chromatography: Bio-Gel P-6; (Ref. 4602)
Helicobacter pylori type strain P466




301
Lipopolysaccharide of the Helicobacter pylori type strain MO19
CLS4603
Shoichi Kusumoto
C99H168NO84P 2747.323 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: NOESY, ROESY, HMBC; (Ref. 4602)
FAB-MS; (Ref. 4602)

Gel-permeation chromatography: Bio-Gel P-6; (Ref. 4602)
Helicobacter pylori type strain MO19




302
Escherichia coli O26 O-antigen polysaccharide
CLS4604
Shoichi Kusumoto
C22H38N2O14 554.542 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, HMQC, HMBC; (Ref. 4604)
GC-MS; (Ref. 4604)

Gel-permeation chromatography: Sephadex S-100; (Ref. 4604)
Escherichia coli O26




303
O3 antigen of Stenotrophomonas (Xanthomonas or Pseudomonas) maltophilia
CLS4605
Shoichi Kusumoto
C22H38N2O14 554.542 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, TOCSY, HETCOR, HMBC; (Ref. 4605)
GC-MS; (Ref. 4605)

Sephadex G-50; (Ref. 4605)
Stenotrophomonas (Xanthomonas or Pseudomonas) maltophilia




304
O-specific polysaccharide from Burkholderia pickettii strain NCTC 11149.
CLS4606
Shoichi Kusumoto
C26H45NO18 659.631 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, HMQC, NOE; (Ref. 4606)


Sephadex G-50; (Ref. 4606)
Burkholderia pickettii strain NCTC 11149




305
Capsular polysaccharide of Vibrio anguillarum serotype O:2
CLS4607
Shoichi Kusumoto
PS1
C42H65N11O22 1076.026 Download ChemDraw structure file

[a]D -109.1 (c 0.4, water); (Ref. 4607)
1H NMR, 13C NMR: COSY, TOCSY, HMQC, HMBC; (Ref. 4607)
FAB-MS; (Ref. 4607)

Gel-filtrarion chromatography: Sepharose 6B, Gel-permeation chromatography: Sephadex G-100; (Ref. 4607)
Vibrio anguillarum serotype O:2




306
Capsular polysaccharide of Vibrio anguillarum serotype O:2
CLS4608
Shoichi Kusumoto
PS2
C42H64N10O23 1077.011 Download ChemDraw structure file

[a]D -109.1 (c 0.4, water); (Ref. 4607)
1H NMR, 13C NMR: COSY, TOCSY, HMQC, HMBC; (Ref. 4607)
FAB-MS; (Ref. 4607)

Gel-filtrarion chromatography: Sepharose 6B, Gel-permeation chromatography: Sephadex G-100; (Ref. 4607)
Vibrio anguillarum serotype O:2




307
O-antigen of Vibrio anguillarum serotype O:2
CLS4609
Shoichi Kusumoto
OS-1
C41H64N10O22 1049.001 Download ChemDraw structure file

[a]D -79.3 (c 0.7, water); (Ref. 4607)
1H NMR, 13C NMR: COSY, TOCSY, HMQC, HMBC; (Ref. 4607)
FAB-MS; (Ref. 4607)

Bio-Gel P-2; (Ref. 4607)
Vibrio anguillarum serotype O:2




308
O-antigen of Vibrio anguillarum serotype O:2
CLS4610
Shoichi Kusumoto
OS-2
C43H66N10O23 1091.038 Download ChemDraw structure file

[a]D -79.3 (c 0.7, water); (Ref. 4607)
1H NMR, 13C NMR: COSY, TOCSY, HMQC, HMBC; (Ref. 4607)
FAB-MS; (Ref. 4607)

Bio-Gel P-2; (Ref. 4607)
Vibrio anguillarum serotype O:2




309
Lipopolysaccharide of Pseudomonas fluorescens strain ATCC 49271
CLS4611
Shoichi Kusumoto
C85H138N8O58 2200.024 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, NOE; (Ref. 4611)
GLC-MS; (Ref. 4611)

Gel-permeation chromatography:Sephadex G-50; (Ref. 4611)
Pseudomonas fluorescens strain ATCC 49271




310
Lipopolysaccharide from Coxiella burnetii strain Nine Mile
CLS4612
Shoichi Kusumoto
C50H82O44 1387.160 Download ChemDraw structure file


ESI-MS, FAB-MS, GC-MS; (Ref. 4612)


Coxiella burnetii strain Nine Mile




311
O88 antigen of Escherichia coli O88:K-:H25
CLS4613
Shoichi Kusumoto
C26H45NO20 691.630 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, COSYRCT, NOE; (Ref. 4613)


Sephadex G-50; (Ref. 4613)
Escherichia coli O88:K-:H25




312
O-specific polysaccharide of Acinetobacter baumannii O11
CLS4614
Shoichi Kusumoto
C34H58N2O26 910.822 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, NOESY; (Ref. 4614)


Sephadex G-50: pyridine/acetic acid pH 5.4; (Ref. 4614)
Acinetobacter baumannii O11




313
O-specific polysaccharide of Acinetobacter baumannii O5
CLS4615
Shoichi Kusumoto
C32H52N4O20 812.770 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, TOCSY, NOESY, HMQC; (Ref. 4615)


Sephadex G-50: pyridine/acetic acid pH 5.4; (Ref. 4615)
Acinetobacter baumannii O5




314
Core oligosaccharide in the serotype O8 lipopolysaccharide from Klebsiella pneumoniae
CLS4616
Shoichi Kusumoto
C65110N2O62P2 783098.625 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: COSY, TOCSY, NOESY, HMQC, HMQC-TOCSY, HMBC; (Ref. 4616)


Gel-filtration chromatography: Sephadex G-50, pyridinium acetate (0.05 M, pH 4.7), Anion-exchange chromatography: 0.01 M NaCl buffer, Bio-Gel P2 colummn: pyridium acetate (0.05 M, pH 4.5); (Ref. 4616)
Klebsiella pneumoniaestrains RFK-9 and RFK-11




315
O-polysaccharide of Actinobacillus actinomycetemcomitans serotype b
CLS4617
Shoichi Kusumoto
C20H35NO14 513.490 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, NOESY, HMQC; (Ref. 4617)


Sephadex G-50, pyridinium acetate (0.05 M, pH 4.6); (Ref. 4617)
Actinobacillus actinomycetemcomitans serotype b




316
O-specific polysaccharide of Hafnia alvei strain 1209
CLS4618
Shoichi Kusumoto
C32H53NO26 867.754 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, double-relayed COSY, NOESY, HMBC, HMQC; (Ref. 4618)
MALDI-MS; (Ref. 4618)

Bio-Gel P-10, 0.05 M pyridine/acetic acid pH 5.6; (Ref. 4618)
Hafnia alvei strain 1209




317
O-antigenic polysaccharide of Klebsiella pneumoniae
CLS4619
Shoichi Kusumoto
C30H52O21 748.721 Download ChemDraw structure file
Agglutination tests, ELISA, Cell culture adherence and invasion assays, Entrotoxin and cytotoxin production, Plasmid analysis, Antibiogram; (Ref. 4719)
1H NMR, 13C NMR: COSY, relayed COSY, HMQC; (Ref. 4619)


Gel-filtration chromatography: Sephadex G-50 or Bio-Gel P-2, 1% aqueous pyridinium acetate pH 6.5; (Ref. 4619)
Klebsiella pneumoniae




318
O-specific polysaccharide of an Aeromonas trota strain
CLS4620
Shoichi Kusumoto
C40H68N2O28 1024.965 Download ChemDraw structure file

1H NMR, 13C NMR: NOE, 2D-COSY, relayed COSY; (Ref. 4620)
GLC-MS; (Ref. 4620)

Gel-permeation chromatography: Sephadex G-50, 0.05 M pyridinium acetate pH 4.5; (Ref. 4620)
Aeromonas trota




319
Acidic O-specific polysaccharides of Proteus mirabilis serogroups O30
CLS4621
Shoichi Kusumoto
C32H51N3O23 845.754 Download ChemDraw structure file

1H NMR, 13C NMR: ROESY, COSY, relayed COSY; (Ref. 4621)


Gel chromatography: Sephadex G-50, 0.05 M pyridinium acetate pH 4.5; (Ref. 4621)
Proteus mirabilis serogroups O30




320
Acidic O-specific polysaccharides of Proteus mirabilis serogroups O26
CLS4622
Shoichi Kusumoto
C34H55N3O25 905.806 Download ChemDraw structure file

1H NMR, 13C NMR: ROESY, COSY, relayed COSY, HMQC, heteronuclear COSY; (Ref. 4621)


Gel chromatography: Sephadex G-50, 0.05 M pyridinium acetate pH 4.5; (Ref. 4621)
Proteus mirabilis serogroups O26




321
O-specific polysaccharide of Hafnia alvei strain 1220
CLS4623
Shoichi Kusumoto
C43H75N2O35P 1211.022 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: 2D COSY, TOCSY, ROESY, 13C DEPT; (Ref. 4623)


Gel-permeation chromatography: Sephadex G-50, 0.05 M pyridine/acetic acid pH 5.75; (Ref. 4623)
Hafnia alvei strain 1220




322
O-specific polysaccharide of Ochrobactrum anthropi LMG 3331
CLS4624
Shoichi Kusumoto
C12H22O10 326.297 Download ChemDraw structure file

1H NMR, 13C NMR: 2D COSY(COSYHG), C-H COSY heteronuclear COSY (XHCORRD); (Ref. 4624)


Gel chromatography: Sephadex G-50, water/pyridine/acetic acid (1000/4/10, pH 4.5); (Ref. 4624)
Ochrobactrum anthropi LMG 3331




323
Vibrio salmonicida lipopolysaccharide
CLS4625
Shoichi Kusumoto
C67H119N6O54P3 1965.591 Download ChemDraw structure file

1H NMR, 13C NMR: 2D COSY, TOCSY, NOESY, HMQC, HSQC; (Ref. 4625)


Gel-permeation chromatography: Sephadex 30; (Ref. 4625)
Vibrio salmonicida (strain NCMB 2262)




324
O-specific polysaccharide chain of Campylobacter fetus serotype B
CLS4626
Shoichi Kusumoto
C163H278O112 4029.884 Download ChemDraw structure file

1H NMR, 13C NMR: 2D COSY, ROESY; (Ref. 4626)
GLC-MS; (Ref. 4626)

Gel-permeation chromatography: Sephadex G-50, 0.05 M prydinium acetate pH 4.5 or water; (Ref. 4626)
Campylobacter fetus serotype B




325
O-antigenic polysaccharide from the enteropathogenic Escherichia coli O125
CLS4627
Shoichi Kusumoto
C40H68N2O30 1056.963 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, HOHAHA, HSQC, HSQC-TOCSY, NOESY, HMBC; (Ref. 4627)


Gel-permeation chromatography: Bio-Gel P-2 and Sephacryl S-100 or Sephacryl S-200; (Ref. 4627)
Escherichia coli O125




326
Lipopolysaccharide from Vibrio cholerae O139
CLS4628
Shoichi Kusumoto
C92H158N52O80P3 3365.463 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: COSY, HMQC, TOCSY, 3D NOESY-TOCSY, 3D TOCSY-NOESY; (Ref. 4628)



Vibrio cholerae O139




327
O-specific polysaccharides of Acinetobacter strain 34
CLS4629
Shoichi Kusumoto
C32H52N4O20 812.770 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, COSY-with-one-step-relayed-coherence transfer (COSY-RCT), H,C-heteronuclear-COSY; (Ref. 4629)


Gel-permeation chromatography: Sephadex G-50; (Ref. 4629)
Acinetobacter strain 34




328
O-specific polysaccharides of Acinetobacter strain 108
CLS4630
Shoichi Kusumoto
C46H78N4O31 1183.120 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, COSY-with-one-step-relayed-coherence transfer (COSY-RCT), H,C-heteronuclear-COSY; (Ref. 4629)


Gel-permeation chromatography: Sephadex G-50; (Ref. 4629)
Acinetobacter strain 108




329
O-specific polysaccharide of Proteus penneri 52
CLS4631
Shoichi Kusumoto
C38H62N4O27 1006.910 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, TOCSY; (Ref. 4631)


Gel-permeation chromatography: Sephadex G-50; (Ref. 4631)
Proteus penneri 52




330
Escherichia coli (EIEC) O28 O-antigenic polysaccharide
CLS4632
Shoichi Kusumoto
C27H47N2O22P 782.636 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: COSY, NOESY, HSQC, HETCOR, HMBC; (Ref. 4632)
FAB-MS; (Ref. 4632)

Gel-permeation chromatography: Bio-Gel P-2, 1% 1-butanol in water; (Ref. 4632)
Escherichia coli (EIEC) O28




331
O-antigenic polysaccharide from an Aeromonas caviae strain
CLS4633
Shoichi Kusumoto
C42H69N3O31 1111.999 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, NOESY, HMBC; (Ref. 4633)


Bio-Gel P-2, 1% 1-butanol in water; (Ref. 4633)
Aeromonas caviae strain 11212




332
O-antigen polysaccharide from the enteroinvasive Escherichia coli (EIEC) O143
CLS4634
Shoichi Kusumoto
C35H55N3O26 933.816 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, TOCSY, NOESY, HSQC, HMBC; (Ref. 4634)


Bio-Gel P-2; (Ref. 4634)
Escherichia coli (EIEC) O143




333
O-specific chain of Hafnia alvei strain 32 lipopolysaccharide
CLS4635
Shoichi Kusumoto
C38H60N2O28 992.880 Download ChemDraw structure file

1H NMR, 13C NMR: dq-COSY, TOCSY, NOESY, HMQC; (Ref. 4635)
MALDI-TOF-MS, FAB-MS; (Ref. 4635)

Bio-Gel P-10, Bio-Gel P-2, Sephadex G-15; (Ref. 4635)
Hafnia alvei strain 32




334
O-specific polysaccharide of Hafnia alvei PCM 1185
CLS4636
Shoichi Kusumoto
C38H63N3O27 993.911 Download ChemDraw structure file

1H NMR, 13C NMR: heteronuclear COSY, ROESY, HMQC; (Ref. 4636)


Gel-permeation chromatography: Sephadex G-50; (Ref. 4636)
Hafnia alvei PCM 1185




335
O-specific polysaccharide of Proteus penneri strains 19 and 35
CLS4637
Shoichi Kusumoto
C25H42N2O18 658.604 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, ROESY, HMQC; (Ref. 4637)


Gel-permeation chromatography: Sephadex G-50, TSK HW-40; (Ref. 4637)
Proteus penneri strains 19 and 35




336
O-acetylated core of Legionella pneumophila serogroup 1 lipopolysaccharide
CLS4638
Shoichi Kusumoto
C58H91N3O39 1454.340 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, NOE, HMQC; (Ref. 4638)


Gel-permeation chromatography: Sephadex G-50; (Ref. 4638)
Legionella pneumophila serogroup 1




337
Surface polysaccharide from Acinetobacter baumannii O16
CLS4639
Shoichi Kusumoto
C34H58N2O26 910.822 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, NOESY, HMQC; (Ref. 4639)


Sephadex G-50; (Ref. 4639)
Acinetobacter baumannii O16




338
O20 antigen of Stenotrophomonas (Xanthomonas or Pseudomonas) maltophilia
CLS4640
Shoichi Kusumoto
C24H42O18 618.579 Download ChemDraw structure file

1H NMR, 13C NMR: COSY, relayed COSY, NOESY, HMQC; (Ref. 4640)
FAB-MS; (Ref. 4640)

Sephadex G-50; (Ref. 4640)
Stenotrophomonas (Xanthomonas or Pseudomonas) maltophilia




339
O-specific polysaccharide of Hafnia alvei PCM 1222
CLS4641
Shoichi Kusumoto
C39H67N2O32P 1106.917 Download ChemDraw structure file

1H NMR, 13C NMR and 31P NMR: NOE, COSY, relayed COSY, TOCSY, ROESY, TORO, HMQC; (Ref. 4641)


Sephadex G-50; (Ref. 4641)
Hafnia alvei PCM 1222




340
Oligosaccharides isolated from the lipopolysaccharide of Moraxella catarrhalis serotype B, strain CCUG 3292
CLS4642
Shoichi Kusumoto
C56H94O48 1535.317 Download ChemDraw structure file