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

    Research output: Contribution to journalArticle

    6 Citations (Scopus)

    Abstract

    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
    Volume339
    Issue number7
    DOIs
    Publication statusPublished - 2004

    Cite this