Boronic acid receptors for alpha-hydroxycarboxylates: high affinity of Shinkai's glucose receptor for tartrate

J Org Chem. 2002 Jul 26;67(15):5426-8. doi: 10.1021/jo025876y.

Abstract

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(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.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boronic Acids* / pharmacokinetics
  • Carboxylic Acids*
  • Chemistry, Organic / methods
  • Chromatography, High Pressure Liquid
  • Malates / chemistry
  • Malates / pharmacokinetics
  • Molecular Structure
  • Receptors, Cell Surface* / chemistry
  • Spectroscopy, Fourier Transform Infrared
  • Tartrates / chemistry
  • Tartrates / pharmacokinetics

Substances

  • Boronic Acids
  • Carboxylic Acids
  • Malates
  • Receptors, Cell Surface
  • Tartrates
  • glucose receptor