Boronic acid receptors for α-hydroxycarboxylates:: High affinity of Shinkai's glucose receptor for tartrate

被引：92

作者：

Gray, CW ^{[1
]}

Houston, TA ^{[1
]}

机构：

[1] Virginia Commonwealth Univ, Dept Chem, Richmond, VA 23284 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 15期

关键词：

D O I：

10.1021/jo025876y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The glucose receptor I developed by Shinkai was synthesized by known methods and with modifications involving the final synthetic step, installation of the phenylboronic acid moieties. Binding of the bis(alpha-hydroxycarbolxylate), tartrate, was assessed and compared to the corresponding bis(diol), erythritol, as well as the corresponding mono(alpha-hydoxycarboxylate), malate. These results suggest that bisboronate/bis(alpha-hydoxycarboxylate) interactions are stronger than the corresponding bisboronate/bis(diol) interactions. Furthermore, we report that the receptor is an order of magnitude more selective for tartrate than malate.

引用

页码：5426 / 5428

页数：3

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