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
收藏
页码：1479 / 1489
页数：11
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