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Lipopolysaccharide


DATA No : CLS2008 INFORMANT : Shoichi Kusumoto

NAME : 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

COMMON NAME: Biosynthetic precursor of lipid A analogue with hydroxy fatty acid S-type
SYMBOL:
FORMULA: C68H130N2O23P2 MOL.WT (average) : 1405.707


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BIOLOGICAL ACTIVITY
IL-6 inhibiting activity; (Ref. 2010)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

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

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

CHEMICAL SYNTHESIS
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)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[2004]
AUTHOR:Oikawa,M., Wada,A., Yishizaki,H., Fukase,K., and Kusumoto, S.
TITLE:New Efficient Synthesis of a Biosynthetic Precursor of Lipid A.
JOURNAL:Bull. Chem. Soc. Jpn.
VOL:70 PAGE : 1435 -1440 (1997)
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[2005]
AUTHOR:Imoto,M., Yoshimura,H., Yamamoto,M. Shimamoto,T., Kusumoto, S., and Shiba, T.
TITLE:Chemical Synthesis of Phosphorylated Tetraacyl Disaccaride Corresponding to a Biosynthetic precursor of Lipid A.
JOURNAL:Tetrahedron Lett.
VOL:25 PAGE : 2667 -2670 (1984)
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[2006]
AUTHOR:Imoto,M., Yoshimura,H., Yamamoto,M., Shimamoto,T., Kusumoto, S., and Shiba, T.
TITLE:Chemical Synthesis of a Biosynthetic Precursor of Lipid A with a Phosphorylated Tetraacyl Disaccharide Structure.
JOURNAL:Bull. Chem. Soc. Jpn
VOL:60 PAGE : 2197 -2204 (1987)
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[2010]
AUTHOR:Liu,Wen-Chi, Oikawa,M., Suda,Y, Fukase,K., Winarno,H., Mori,S., Hashimoto,M., and Kusumoto, S.
TITLE:Enzymatic Preparation of (S)-3-Hydroxytetradecanoic Acid and Synthesis of Unnatural Analogues of Lipid A Containing the (S)-Acid.
JOURNAL:Bull. Chem. Soc. Jpn.
VOL:70 PAGE : 1441 -1450 (1997)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.