The synthesis of some deoxygenated analogues of early intermediates in the biosynthesis of glycosylphosphatidylinositol (GPI) membrane anchors

Alexander P. Dix, Charles N. Borissow, Michael A. J. Ferguson, John S. Brimacombe

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    6 Citations (Scopus)


    Syntheses are described of 2-azido-4,6-di-O-benzyl-2,3-dideoxy-D-ribo-hexopyranosyl fluoride, 6-O-acetyl-2-azido-3-O-benzyl-2,4-dideoxy-D-oxylo-hexopyranosyl fluoride and 2-azido-3,4-di-O-benzyl-2,6-dideoxy-D-glucopyranosyl fluoride. These glycosyl donors were coupled with the acceptor 1D-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-myo-inositol and the alpha-coupled products were transformed into alpha-D-3dGlcpN-PI, alpha-D-4dGlcpN-PI and alpha-D-6dGlcpN-PI by way of the H-phosphonate route. Brief mention is made of the biological evaluation of these deoxy-sugar analogues and their N-acetylated forms as candidate substrate/inhibitors of the N-deacetylase and alpha-(1-->4)-D-mannosyltransferase activities present in trypanosomal and HeLa (human) cell-free system. (C) 2004 Published by Elsevier Ltd.

    Original languageEnglish
    Pages (from-to)1263-1277
    Number of pages15
    JournalCarbohydrate Research
    Issue number7
    Publication statusPublished - 2004

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