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Glycosphingolipid


DATA No : GSG3034 INFORMANT : Hideharu Ishida

NAME : N-acetylneraminyla2-3galactosylb1-3(fucosyla1-4)N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide

COMMON NAME: sialyl-Lea
SYMBOL:
FORMULA: C79H141N3O36 MOL.WT (average) : 1708.963


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:-18.8deg(Ref. 3022)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:1D 1H-NMR (Ref. 3022)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Chemical Synthesis
CHEMICAL SYNTHESIS
Methylsulfenyl bromide-silver triflate-promoted coupling of 2-(trimethylsilyl)ethyl O-(2-acetamido-6-O-benzy-2-deoxy-b-D-glucopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside afforded the pentasaccharide in good yield. Glycosylation of the pentasaccharide with methyl 2,3,4-tri-O-benzyl-1-thio-b-L-fucopyranoside by use of N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid (TfOH) as a promoter, gave the desired hexasaccharide.
This was converted into the a-trichloroacetimidate, via reductive removal of benzyl groups, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and treatment with trichloroacetonitrile, 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, coupling with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the title ganglioside in good yield. (Ref. 3022)
METABOLISM

GENETIC INFORMATION

NOTE
Fatty acid C18:0

LCB d18:1
REFERENCES
[3022]
AUTHOR:Kameyama, A., Ishida, H., Kiso, M., and Hasegawa, A.
TITLE:Total synthesis of tumor-associated ganglioside, sialyl-Lea.
JOURNAL:Journal of Carbohydrate Chemistry
VOL:135 PAGE : 641 -654 (1994)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.