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

被引:23
作者
Crossman, A
Brimacombe, JS
Ferguson, MAJ
机构
[1] UNIV DUNDEE,DEPT CHEM,DUNDEE DD1 4HN,SCOTLAND
[2] UNIV DUNDEE,DEPT BIOCHEM,DUNDEE DD1 4HN,SCOTLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 18期
关键词
D O I
10.1039/a701881i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:2769 / 2774
页数:6
相关论文
共 20 条
[1]   PARASITE GLYCOCONJUGATES .1. THE SYNTHESIS OF SOME EARLY AND RELATED INTERMEDIATES IN THE BIOSYNTHETIC-PATHWAY OF GLYCOSYL-PHOSPHATIDYLINOSITOL MEMBRANE ANCHORS [J].
COTTAZ, S ;
BRIMACOMBE, JS ;
FERGUSON, MAJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (23) :2945-2951
[2]   PARASITE GLYCOCONJUGATES .3. SYNTHESIS OF SUBSTRATE-ANALOGS OF EARLY INTERMEDIATES IN THE BIOSYNTHETIC-PATHWAY OF GLYCOSYLPHOSPHATIDYLINOSITOL MEMBRANE ANCHORS [J].
COTTAZ, S ;
BRIMACOMBE, JS ;
FERGUSON, MAJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (13) :1673-1678
[3]   PREPARATION OF DIVERSELY PROTECTED 2-AZIDO-2-DEOXYGLYCOPYRANOSES FROM GLYCALS [J].
CZERNECKI, S ;
AYADI, E .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1995, 73 (03) :343-350
[4]   THE STRUCTURE AND BIOSYNTHESIS OF GLYCOSYL PHOSPHATIDYLINOSITOL PROTEIN ANCHORS [J].
ENGLUND, PT .
ANNUAL REVIEW OF BIOCHEMISTRY, 1993, 62 :121-138
[5]   GLYCOSYL-PHOSPHATIDYLINOSITOL MOIETY THAT ANCHORS TRYPANOSOMA-BRUCEI VARIANT SURFACE GLYCOPROTEIN TO THE MEMBRANE [J].
FERGUSON, MAJ ;
HOMANS, SW ;
DWEK, RA ;
RADEMACHER, TW .
SCIENCE, 1988, 239 (4841) :753-759
[6]   Lipid anchors on membrane proteins [J].
Ferguson, Michael A. J. .
CURRENT OPINION IN STRUCTURAL BIOLOGY, 1991, 1 (04) :522-529
[7]   THE ROLE OF INOSITOL ACYLATION AND INOSITOL DEACYLATION IN GPI BIOSYNTHESIS IN TRYPANOSOMA-BRUCEI [J].
GUTHER, MLS ;
FERGUSON, MAJ .
EMBO JOURNAL, 1995, 14 (13) :3080-3093
[8]  
KINZY W, 1985, LIEBIGS ANN CHEM, P1537
[9]   A GENERAL-METHOD FOR THE SYNTHESIS OF GLYCEROPHOSPHOLIPIDS AND THEIR ANALOGS VIA H-PHOSPHONATE INTERMEDIATES [J].
LINDH, I ;
STAWINSKI, J .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1338-1342
[10]   A CONVENIENT AND GENERAL-APPROACH TO THE SYNTHESIS OF PROPERLY PROTECTED D-NUCLEOSIDE-3'-HYDROGENPHOSPHONATES VIA PHOSPHITE INTERMEDIATES [J].
MARUGG, JE ;
TROMP, M ;
KUYLYEHESKIELY, E ;
VANDERMAREL, GA ;
VANBOOM, JH .
TETRAHEDRON LETTERS, 1986, 27 (23) :2661-2664