Boronic Acid Receptors for α-Hydroxycarboxylates:  High Affinity of Shinkai's Glucose Receptor for Tartrate

The glucose receptor 1 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(α-hydroxycarbolxylate), tartrate, was assessed and compared to the corresponding bis(diol), eryt...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-07, Vol.67 (15), p.5426-5428
Main Authors: Gray, Charles W, Houston, Todd A
Format: Article
Language:English
Subjects:
B derivatives
Boronic Acids - pharmacokinetics
Carboxylic Acids
Chemistry
Chemistry, Organic - methods
Chromatography, High Pressure Liquid
Exact sciences and technology
Malates - chemistry
Malates - pharmacokinetics
Molecular Structure
Organic chemistry
Organometalloidal and organometallic compounds
Preparations and properties
Receptors, Cell Surface - chemistry
Spectroscopy, Fourier Transform Infrared
Tartrates - chemistry
Tartrates - pharmacokinetics
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Summary:The glucose receptor 1 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(α-hydroxycarbolxylate), tartrate, was assessed and compared to the corresponding bis(diol), erythritol, as well as the corresponding mono(α-hydoxycarboxylate), malate. These results suggest that bisboronate/bis(α-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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo025876y