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Glycosphingolipid


DATA No : GSG3010 INFORMANT : Hideharu Ishida

NAME : N-acetylneraminyla2-6galactosylb1-4-N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide

COMMON NAME: sialyl-(2-6)-neolactotetraosylceramide/sialyl(2-6)-paragloboside
SYMBOL:
FORMULA: C73H131N3O32 MOL.WT (average) : 1562.822


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:-1.5deg(Ref. 3006)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:1D 1H-NMR (Ref. 3006)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Chemical Synthesis
CHEMICAL SYNTHESIS
Methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-6)-2,4-di-O-benzoyl-3-O-benzyl-1-thio-b-D-galactopyranoside, the key glycosyl donor was prepared, via glycosylation of 2-(trimethylsilyl)ethyl 3-O-benzyl-b-D-galactopyranoside with the methyl a-thio-glycoside of N-acetylneuraminic acid, benzoylation, replacement of the 2-(trimethylsilyl)ethyl group by acetyl, and introduction of the methylthio group with (methylthio)-trimethylsilane. Coupling of 2-(trimethylsilyl)ethyl O-(2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1-3')-per-O-benzyl-b-lactoside with the disaccharide donor gave the pentasaccharide in good yields.
The oligosaccaride was converted into the corresponding a-trichloroacetimidate which, on coupling with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycoside. Finally, the compound was transformed, via selective reduction of the azide group, condensation with octadecanoic acid, O-de-acylation, and hydrolysis of the methyl ester group, into the final compound. (Ref. 3006)
METABOLISM

GENETIC INFORMATION

NOTE
Fatty acid C18:0

LCB d18:1
REFERENCES
[3006]
AUTHOR:Hasegawa, A., Hotta, K., Kameyama, A., Ishida, H., and Kiso, M.
TITLE:Total synthesis of sialyl-a(2-6)-lactotetraosylceramide and sialyl-a(2-6)-neolactotetraosylceramide.
JOURNAL:Journal of Carbohydrate Chemistry
VOL:10 PAGE : 439 -459 (1991)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.