Synthesis of 1-C-linked diphosphate analogues of UDP-N-Ac-glucosamine and UDP-N-Ac-muramic acid

被引：26

作者：

Babic, Andrej ^{[1
]}

Gobec, Stanislav ^{[1
]}

Gravier-Pelletier, Christine ^{[2
]}

Le Merrer, Yves ^{[2
]}

Pecar, Slavko ^{[1
,3
]}

机构：

[1] Univ Ljubljana, Fac Pharm, Ljubljana 1000, Slovenia

[2] Univ Paris 05, CNRS, UMR 8601, Chim & Biochim Pharmacol & Toxicol Lab, F-75006 Paris, France

[3] Jozef Stefan Inst, Ljubljana 1000, Slovenia

来源：

TETRAHEDRON | 2008年 / 64卷 / 38期

关键词：

C-linked glycosides substrate analogues; diphosphate isosteres; microwave-assisted synthesis;

D O I：

10.1016/j.tet.2008.07.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

UDP-N-acetyl-glucosamine and UDP-N-acetyl-muramic acid are two important cytoplasmic precursors of bacterial peptidoglycan. The convergent synthesis of their analogues is reported. The alpha-1-C-linked-N-acetyl-glucosamine was synthesized using microwave-assisted Keck radical allylation. Oxidation of alkene derivatives to the corresponding carboxylic acids allowed attachment to O- and N-sulfamoyluridine giving stable diphosphate mimetics. (C) 2008 Elsevier Ltd. All rights reserved.

引用

收藏

页码：9093 / 9100

页数：8

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