TY - JOUR
T1 - Parasite glycoconjugates
T2 - Part 7. Synthesis of further substrate analogues of early intermediates in the biosynthetic pathway of glycosylphosphatidylinositol membrane anchors
AU - Crossman, Arthur
AU - Brimacombe, John S.
AU - Ferguson, Michael A. J.
PY - 1997/9/21
Y1 - 1997/9/21
N2 - 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.
AB - 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.
U2 - 10.1039/A701881I
DO - 10.1039/A701881I
M3 - Article
SN - 0300-922X
SP - 2769
EP - 2774
JO - Journal of the Chemical Society - Perkin Transactions 1
JF - Journal of the Chemical Society - Perkin Transactions 1
IS - 18
ER -