PARASITE GLYCOCONJUGATES .7. SYNTHESIS OF FURTHER SUBSTRATE-ANALOGS OF EARLY INTERMEDIATES IN THE BIOSYNTHETIC-PATHWAY OF GLYCOSYLPHOSPHATIDYLINOSITOL MEMBRANE ANCHORS

Substrate analogues of amino-2-deoxy-alpha-D-glucopyranosyl)-myo-inosi tol 1-[sn-2,3-bis(myristoyloxy)propyl phosphate], an early intermediat e in the biosynthesis of glycosylphosphatidylinositol (GPI) membrane a nchors, have been prepared for biological evaluation with the alpha-(1 -->4)-D-mannosyltransferase of the protozoan parasite Trypanosoma bruc ei, The analogue alpha-D-GlcpNH(2)-(1-->6)-2-OMe-PI2 is a substrate fo r the protozoan alpha-(1-->4)-D-mannosyltransferase but not for the co rresponding mammalian enzyme, whereas the analogues 3 and 4, in which the fatty-acid groups of the natural substrate are replaced by alkyl g roups, are acceptable substrates for both the protozoan and mammalian enzymes.