Affinity Enhancement by Dendritic Side Chains in Synthetic Carbohydrate Receptors

被引：63

作者：

Destecroix, Harry ^{[1
]}

Renney, Charles M. ^{[1
]}

Mooibroek, Tiddo J. ^{[1
]}

Carter, Tom S. ^{[1
]}

Stewart, Patrick F. N. ^{[1
]}

Crump, Matthew P. ^{[1
]}

Davis, Anthony P. ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 07期

基金：

英国工程与自然科学研究理事会;

关键词：

carbohydrates; dendrimers; molecular recognition; receptors; supramolecular chemistry; MOLECULAR RECOGNITION; SUPRAMOLECULAR CHEMISTRY; LECTIN; WATER; DISACCHARIDE; BINDING; SACCHARIDES; MEDIA;

D O I：

10.1002/anie.201409124

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dendritic side chains have been used to modify the binding environment in anthracene-based synthetic carbohydrate receptors. Control of length, charge, and branching enabled the positioning of side-chain carboxylate groups in such a way that they assisted in binding substrates rather than blocking the cavity. Conformational degeneracy in the dendrimers resulted in effective preorganization despite the flexibility of the system. Strong binding was observed to glucosammonium ions in water, with K-a values up to 7000M(1). Affinities for uncharged substrates (glucose and N-acetylglucosamine) were also enhanced, despite competition from solvent and the absence of electrostatic interactions.

引用

页码：2057 / 2061

页数：5

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