Lipopolysaccharide

DATA No : CLS2002 INFORMANT : Shoichi Kusumoto

NAME : 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

COMMON NAME	:	Biosynthetic precursor of lipid A from Escherichia coli
SYMBOL	:	#406, LA-14-PP
FORMULA	:	C₆₈H₁₃₀N₂O₂₃P₂ MOL.WT (average) : 1405.707

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BIOLOGICAL ACTIVITY

IL-6 inhibiting activity; (Ref. 2007)

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:

DENSITY	:

SOLUBILITY	:

SPECTRAL DATA

UV SPECTRA	:

IR SPECTRA	:

NMR SPECTRA	:	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)

MASS SPECTRA	:	ESI-MS (negative, API III) m/z 1404.9 [(M-H)^-]

OTHER SPECTRA	:

CHROMATOGRAM DATA

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

SOURCE

Escherichia coli

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, 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)

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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[2007]

AUTHOR	:	Fukase,K., Fukase,Y., Oikawa,M., Wen-Chi Liu, Suda.Y., and Kusumoto, S.
TITLE	:	Divergent Synthesis and Biological Activities of Lipid A Analogues of Shorter Acyl Chains.
JOURNAL	:	Tetrahedron
VOL	:	54 PAGE : 4033 -4050 (1998)

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