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Glycosphingolipid


DATA No : GSG3014 INFORMANT : Hideharu Ishida

NAME : N-acetyl-galactosaminylb1-4(N-acetylneraminyla2-3)galactosylb1-4glucosylceramide

COMMON NAME:
SYMBOL: GM2
FORMULA: C67H121N3O26 MOL.WT (average) : 1384.682


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:+11.3deg(Ref. 3010)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:1D 1H-NMR (Ref. 3010)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Chemical Synthesis
CHEMICAL SYNTHESIS
Coupling of 2- (trimethylsilyl)ethyl O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside, prepared from 2-(trimethylsilyl)ethyl b-lactoside by selective 3',4'-O-isopropylidenation, O-benzylation, and subsequent removal of the isopropylidene group, with methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate using N-iodosuccinimide (NIS), gave the trisaccharide), which on condensation with methyl 6-O-benzoyl -2-deoxy-3,4-O-isopropylidene-2-phthalimido-1-thio-b-D-galactopyranoside , gave the protected ganglioside GM2 oligosaccharide.
This was transformed, via O-deisopropylidenation, O-acetylation, removal of the phthaloyl group, N-acetylation, removal of the benzyl groups followed by O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the final glycosyl donor. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the a-trichloroacetimidate gave the b-glycoside, which on channeling through selective reduction of the azide group, coupling of the amino group with octadecanoic acid, O-deacylation and saponification of the methyl ester group, gave the title ganglioside. (Ref. 3010)
METABOLISM

GENETIC INFORMATION

NOTE
Fatty acid C18:0

LCB d18:1
REFERENCES
[3010]
AUTHOR:Hasegawa, A., Nagahama, T., Ohki, H., and Kiso, M.
TITLE:A facile total synthesis of ganglioside GM2.
JOURNAL:Journal of Carbohydrate Chemistry
VOL:11 PAGE : 699 -714 (1992)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.