Parasite glycoconjugates: Part 7. Synthesis of further substrate analogues of early intermediates in the biosynthetic pathway of glycosylphosphatidylinositol membrane anchors

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    Abstract

    Substrate analogues of 1D-6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-myo-inositol 1-[sn-2,3-bis(myristoyloxy)propyl phosphate], an early intermediate in the biosynthesis of glycosylphosphatidylinositol (GPI) membrane anchors, have been prepared for biological evaluation with the alpha-(1-->4)-D-mannosyltransferase of the protozoan parasite Trypanosoma brucei, The analogue alpha-D-GlcpNH(2)-(1-->6)-2-OMe-PI2 is a substrate for the protozoan alpha-(1-->4)-D-mannosyltransferase but not for the corresponding mammalian enzyme, whereas the analogues 3 and 4, in which the fatty-acid groups of the natural substrate are replaced by alkyl groups, are acceptable substrates for both the protozoan and mammalian enzymes.

    Original languageEnglish
    Pages (from-to)2769-2774
    Number of pages6
    JournalJournal of the Chemical Society - Perkin Transactions 1
    Issue number18
    DOIs
    Publication statusPublished - 21 Sep 1997

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