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  • Title: Synthesis of disialoganglioside GD1 alpha and its positional isomer.
    Author: Prabhanjan H, Aoyama K, Kiso M, Hasegawa A.
    Journal: Carbohydr Res; 1992 Sep 02; 233():87-99. PubMed ID: 1446313.
    Abstract:
    The first total syntheses of disialoganglioside GD1 alpha and its alpha 2-6 positional isomer are described. Suitably protected pentasaccharide derivatives, derived from known pentasaccharide precursors, were selected as the glycosyl acceptors. Using our facile method of stereoselective alpha-glycosidation of sialic acid, these acceptors were coupled with methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galact o-2- nonulopyranosid)onate in acetonitrile medium in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) to get the desired di-alpha-sialyl hexasaccharide derivatives in moderate yields. The hexasaccharide trichloroacetimidates upon coupling with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the corresponding beta-linked sphingosine glycosides in high yields. These were 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 GD1 alpha and its positional isomer having the main-chain residue 2-6 linked.
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