Chemical synthesis of UDP-4-O-methyl-GlcNAc, a potential chain terminator of chitin synthesis

被引：16

作者：

Chang, R ^{[1
]}

Moquist, P ^{[1
]}

Finney, NS ^{[1
]}

机构：

[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA

来源：

CARBOHYDRATE RESEARCH | 2004年 / 339卷 / 08期

关键词：

chitin synthase; glucosamine; 4-O-methyl-GlcNAc; UDP-sugar analog; synthesis;

D O I：

10.1016/j.carres.2004.03.014

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Chitin synthase converts uridine diphosphoryl-N-acetylglucosamine (UDP-GlcNAc) to chitin (poly-beta-(1 --> 4)-GlcNAc). During polymerization, elongation occurs at the 4-OH (nonreducing) terminus of the growing chitin chain. Blockage of the 4-OH via incorporation of UDP-N-acetyl-4-O-methylglucosamine (UDP-4-OMe-GlcNAc, 3) can potentially terminate chitin polymerization, and represents a novel strategy for chitin synthase inhibition. The chemical synthesis of 3 and preliminary evaluation of its possible incorporation by chitin synthase are reported herein. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1531 / 1536

页数：6

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