Lipopolysaccharide

DATA No : CLS2005 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-(6-¹³C)-glucopyranose 1,4'-Bisphosphate

COMMON NAME	:	6-¹³C-labeled biosynthetic precursor of lipid A
SYMBOL	:	#406, LA-15-PH
FORMULA	:	C₆₈H₁₃₀N₂O₂₃P₂ MOL.WT (average) : 1405.707

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BIOLOGICAL ACTIVITY

IL-6 inhibiting activity; (Ref. 2001)

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), 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)

MASS SPECTRA	:	ESI-MS (nagative 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

(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.

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES

[2001]

AUTHOR	:	Wen-Ci Liu, Oikawa,M., Fukase,K., Suda,Y., and Kusumoto,S.
TITLE	:	A Divergent Synthesis of Lipid A and Its Chemically Stable Unnatural Analogues.
JOURNAL	:	Bull. Chem. Soc. Jpn
VOL	:	72 PAGE : 1377 -1385 (1999)

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[2009]

AUTHOR	:	Oikawa,M., Shintaku,T., Sekljik,H., Fukase,K., and Kusumoto, S.
TITLE	:	Synthesis of ¹³C-Labeled Biosynthetic Precursor of Lipid A and Its Analogue with Shorter Acyl Chains.
JOURNAL	:	Bull. Chem. Soc. Jpn.
VOL	:	72 PAGE : 1857 -1867 (1999)

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