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

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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(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.