Glycosphingolipid

DATA No : GSG3043 INFORMANT : Hideharu Ishida

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

COMMON NAME	:
SYMBOL	:	GT1a
FORMULA	:	C₉₅H₁₆₅N₅O₄₇ MOL.WT (average) : 2129.332

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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:	+2.0(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-6-O-benzyl-2-deoxy-b-D-galactopyranosyl)-(1-4)-O-[methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)]-O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyra-noside in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) gave the heptasaccharide 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 ganglioside GT1a 19. (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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