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Glycosphingolipid


DATA No : GSG3023 INFORMANT : Hideharu Ishida

NAME : KDNa2-6galactosylb1-4-N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide

COMMON NAME: KDN-(2-6)-neolactotetraosylceramide/sialyl-(2-6)-paragloboside
SYMBOL:
FORMULA: C75H136N2O32 MOL.WT (average) : 1577.877


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:-6.1deg(Ref. 3015)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:1D 1H-NMR (Ref. 3015)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Chemical Synthesis
CHEMICAL SYNTHESIS
Methyl O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-6)-2,4-di-O-benzoyl-3-O-benzyl-1-thio-b-D-galactopyranoside was prepared from the phenyl b-thioglycoside derivative of KDN and 2-(trimethylsilyl)ethyl 3-O-benzyl-b-D-galactopyranosidein four steps. Coupling of 2-(trimethylsilyl)ethyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1-3')-per-O-benzyl-b-D-lactoside, with the donor gave the pentasaccharidein good yields. This pentasaccharide was converted into the corresponding a-trichloroacetimidate which, on glycosylation with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycoside. Finally, this was transformed, via selective reduction of the azido group, condensation with octadecanoic acid, O-deacylation, and saponification of the methyl ester group, into the target compound. (Ref. 3015)
METABOLISM

GENETIC INFORMATION

NOTE
Fatty acid C18:0

LCB d18:1
REFERENCES
[3015]
AUTHOR:Terada, T., Ishida, H., Kiso, M., and Hasegawa, A.
TITLE:Synthesis of KDN-a-(2-6)-lactotetraosylceramide and KDN-a-(2-6)-neolactotetraosylceramide.
JOURNAL:Journal of Carbohydrate Chemistry
VOL:146 PAGE : 751 -768 (1995)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.