First synthesis of a malarial prototype: a fully lipidated and phosphorylated GPI membrane anchor

被引：20

作者：

Lu, J ^{[1
]}

Jayaprakash, KN ^{[1
]}

Fraser-Reid, B ^{[1
]}

机构：

[1] Nat Prod & Glycotechnol Res Inst Inc, NPG, Durham, NC 27706 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 04期

关键词：

D O I：

10.1016/j.tetlet.2003.10.179

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A strategy is described for syntheses of a fully lipidated and phosphorylated prototype of the GPI of Plasmodium falciparum, the causative agent of lethal cerebral, drug-resistant malaria. Orthoesters, prepared in four steps from D-mannose, and methyl alpha-D-glucopyranoside are the key starting materials. The latter furnishes the inositol moiety using Bender's procedure, while the former gives the other four units of the pseudo-pentasaccharide. The strategy for installing the three biologically important acyl units of the phosphomositide has been worked out. The critical, biosynthetically important C2-O-acyl group of the inositol is exceptionally stable, showing no tendency to migrate to the cis-related C3-OH in several test substrates. (C) 2003 Elsivier Ltd. All rights reserved.

引用

页码：879 / 882

页数：4