Boronic acid receptors for alpha-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(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.
Department of Chemistry, Virginia Commonwealth University, Richmond, Virginia 23284, USA.
Charles W
CW
Gray
Todd A
TA
Houston
D001897:Boronic Acids / Q000493:pharmacokinetics; D002264:Carboxylic Acids; D002625:Chemistry, Organic / Q000379:methods; D002851:Chromatography, High Pressure Liquid; D008293:Malates / Q000737:chemistry / Q000493:pharmacokinetics; D015394:Molecular Structure; D011956:Receptors, Cell Surface / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared; D013644:Tartrates / Q000737:chemistry / Q000493:pharmacokinetics
D001897:Boronic Acids; D002264:Carboxylic Acids; D008293:Malates; D011956:Receptors, Cell Surface; D013644:Tartrates; C027786:glucose receptor