Back to HOME

Glycosphingolipid


DATA No : GSG3046 INFORMANT : Hideharu Ishida

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

COMMON NAME:
SYMBOL: GD1b
FORMULA: C95H165N5O48 MOL.WT (average) : 2145.331


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:-12.9deg(Ref. 3030)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:1D 1H-NMR (Ref. 3030)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Chemical Synthesis
CHEMICAL SYNTHESIS
Glycosylation of 2-(trimethylsilyl)ethyl O-(2-acetamido-6-O-benzyl-2-deoxy-3,4-O-iso-propylidene-b-D-galactopyranosyl)-(1-4)-O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with methyl [phenyl 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-2-thio-D-glycero-D-galacto-2-nonulopyra-nosid]onate using N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid (TfOH) in acetonitrile gave the protected GD2 pentasaccharide, which was converted into the pentasaccharide acceptor by de-O-isopropylidenation.
Glycosylation of the acceptor with methyl thioglycoside derivative of sialyl galactose by use of dimethyl(methylthio)sulfonium triflate (DMTST) gave the protected ganglioside GT1b oligosaccharide. This was transformed into the corresponding a-trichloroacetimidate via reductive removal of benzyl groups, O-acetylation, selective removal of 2-(trimethylsilyl)ethyl group, and treatment of trichloroacetonitrile. Condensation of the imidate with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the corresponding b-glycoside, which was converted, via selective reduction of azido group, coupling with octadecanoic acid, de-O-acylation, and saponification of methyl esters and lactone groups, into the corresponding ganglioside GT1b.(Ref. 3030)
METABOLISM

GENETIC INFORMATION

NOTE
Fatty acid C18:0

LCB d18:1
REFERENCES
[3030]
AUTHOR:Ishida, H.-K., Ishida, H., Kiso, M., and Hasegawa, A.
TITLE:Total synthesis of ganglioside GQ1b and the related polysialogangliosides.
JOURNAL:Tetrahedron: Asymmetry
VOL:5 PAGE : 2493 -2515 (1994)
[TOP]

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