Back to HOME

Glycosphingolipid


DATA No : GSG3020 INFORMANT : Hideharu Ishida

NAME : KDNa2-3galactosylb1-4(fucosyla1-3)N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide

COMMON NAME: KDN-Lex
SYMBOL:
FORMULA: C81H146N2O36 MOL.WT (average) : 1724.018


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:-16.0deg(Ref. 3013)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:(Ref. 3013)

NMR SPECTRA:1D 1H-NMR (Ref. 3013)

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)-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside was prepared from 2-(trimethylsilyl)ethyl O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-6-O-benzyl-b-D-galactopyra-noside, via O-benzoylation, replacement of the 2-(trimethylsilyl)ethyl group by acetyl, and introduction of the methylthio group with methylthiotrimethylsilane. Glycosylation of 2-(trimethylsilyl)ethyl O-(2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-glucopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside (5) or 2-(trimethylsilyl)ethyl
O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside, prepared from 5 via O-benzylation and reductive opening of the benzylidene acetal ring, with 4 gave the corresponding pentasaccharides 9 and 13 in good yields. In the same way, 4 was reacted with 2-(trimethylsilyl)ethyl O-(2,3,4-tri-O-benzyl-a-L-fucopyranosyl)-(1-3)-O-(2-acetamido-6-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopy-ranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranosidewith the disaccharide donor gave the hexasaccharide. This oligosaccharide was converted via reductive removal of the benzyl groups and benzylidene group, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the corresponding trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the donor in the presence of boron trifluoride etherate afforded the expected b-glycoside, which were transformed via selective reduction of the azido group, coupling with octadecanoic acid, O-deacylation and de-esterification, into the target ganglioside. (Ref. 3013)
METABOLISM

GENETIC INFORMATION

NOTE
Fatty acid C18:0

LCB d18:1
REFERENCES
[3013]
AUTHOR:Terada, T., Kiso, M., and Hasegawa, A.
TITLE:Synthesis of KDN-lactotetraosylceramide, KDN-neolactotetraosylceramide, and KDN-Lewis X ganglioside PubMed ID:8050096
JOURNAL:Carbohydr Res.
VOL:259 PAGE : 201-218 (1994)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.