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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