Synthesis of a small library of bivalent α-D-mannopyranosides for lectin cross-linking

被引：21

作者：

Bergeron-Brlek, Milan ^{[1
]}

Shiao, Tze Chieh ^{[1
]}

Trono, M. Corazon ^{[1
]}

Roy, Rene ^{[1
]}

机构：

[1] Univ Quebec, Dept Chem, PharmaQAM, Montreal, PQ H3C 3P8, Canada

来源：

CARBOHYDRATE RESEARCH | 2011年 / 346卷 / 12期

基金：

加拿大自然科学与工程研究理事会;

关键词：

Library; Mannopyranosides; Lectin; Cross-linking; Palladium catalysis; CONCANAVALIN-A; COUPLING REACTIONS; BINDING; GLYCODENDRIMERS; MULTIVALENCY; RECOGNITION; INHIBITION; GLYCOSIDES; EPITOPES; ADHESION;

D O I：

10.1016/j.carres.2011.03.041

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：

A small library of bivalent alpha-D-mannopyranosides having rigid linkers was constructed in order to evaluate the effects of inter-saccharide distances upon multivalent binding interactions with plant and bacterial lectins. To this end, iodoaryl and propargyl alpha-D-mannopyranosides were synthesized and the former treated with TMS-acetylene under palladium chemistry to provide their corresponding ethynylaryl derivatives. A library of 15 dimeric members was then obtained using Lewis acid catalyzed glycosidation, aryl-aryl homocoupling, transition metal catalyzed Sonogashira cross-coupling reactions, and oxidative Glaser homocoupling. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：1479 / 1489

页数：11

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