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Glycosphingolipid


DATA No : GSG3013 INFORMANT : Hideharu Ishida

NAME : N-acetylneuraminyla2-3galactosylb1-3(N-acetylneuraminyla2-6)N-acetyl- -galactosaminylb1-4galactosylb1-4glucosylceramide

COMMON NAME:
SYMBOL: GD1a
FORMULA: C84H148N4O39 MOL.WT (average) : 1838.077


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BIOLOGICAL ACTIVITY
This ganglioside is enriched in Purkinje cells and may have a role in Purkinje cell functions in the cerebellum. (Ref. 3041)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:+3.4deg(Ref. 3009)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:(Ref. 3009)

NMR SPECTRA:1D 1H-NMR (Ref. 3009)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Chemical Synthesis
CHEMICAL SYNTHESIS
Suitably protected pentasaccharide derivatives, derived from known pentasaccharide precursors, were selected as the glycosyl acceptors. Using our facile method of stereoselective a-glycosidation of sialic acid, these acceptors were coupled with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate in acetonitrile medium in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) to get the desired di-a-sialyl hexasaccharide derivative in moderate yield. The hexasaccharide trichloroacetimidate upon coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the corresponding b-linked sphingosine glycoside in high yield. This was subjected in sequence to selective reduction of the azido group and coupling of the thus formed amino group with octadecanoic acid, O-deacylation, and saponification of the methyl ester groups to obtain ganglioside GD1a . (Ref. 3009)
METABOLISM

GENETIC INFORMATION

NOTE
Fatty acid C18:0

LCB d18:1
REFERENCES
[3009]
AUTHOR:Prabhanjan, H., Aoyama, K., Kiso, M., and Hasegawa, A.
TITLE:Synthesis of disialoganglioside GD1 alpha and its positional isomer PubMed ID:1446313
JOURNAL:Carbohydr Res.
VOL:233 PAGE : 87-99 (1992)
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[3041]
AUTHOR:Furuya, S., Irie, F., Hashikawa, T., Nakazawa, K., Kozakai, A., Hasegawa, A., Sudo, K., and Hirabayashi, Y.
TITLE:Ganglioside GD1 alpha in cerebellar Purkinje cells. Its specific absence in mouse mutants with Purkinje cell abnormality and altered immunoreactivity in response to conjunctive stimuli causing long-term desensitization PubMed ID:7528216
JOURNAL:J Biol Chem.
VOL:269 PAGE : 32418-32425 (1994)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.