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Glycosphingolipid


DATA No : GSG3042 INFORMANT : Hideharu Ishida

NAME : N-acetylneraminyla2-8N-acetylneuraminyla2-3galactosylb1-3N-acetyl- -galactosaminylb1-4galactosylb1-4glucosylceramide

COMMON NAME:
SYMBOL: GD1c
FORMULA: C84H148N4O40 MOL.WT (average) : 1854.077


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:+5.4deg(Ref. 3028)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:1D 1H-NMR (Ref. 3028)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Chemical Synthesis
CHEMICAL SYNTHESIS
Condensation of methyl O-[methyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate]-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-gala-ctopyranoside with 2-(trimethylsilyl)ethyl O-(2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-galactopyranosyl)-(1-4)-O-(2,3,6-tri-O-benzyl-b-D-galactopy-ranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranosidegave the hexasaccharide derivative.
This oligosaccharides was converted into the a-trichloroacetimidate via reductive removal of the benzyl groups and/or benzylidene group, O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group and treatment with trichloroacetonitrile, which, on coupling with 2-azidosphingosine derivative gave the b-glycoside. Finally, this was transformed, via selective reduction of the azido group, coupling with octadecanoic acid and removal of all protecting groups, into the title gangliosides GD1c. (Ref. 3028)
METABOLISM

GENETIC INFORMATION

NOTE
Fatty acid C18:0

LCB d18:1
REFERENCES
[3028]
AUTHOR:Ishida, H.-K., Ando, H., Ito, H., Ishida, H., Kiso, M., and Hasegawa, A.
TITLE:Total synthesis of gangliosides GD1c and GT1a.
JOURNAL:Journal of Carbohydrate Chemistry
VOL:1645 PAGE : 413 -428 (1997)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.