ortho‐(Aminomethyl)phenylboronic acids—synthesis,structure and sugar receptor activity

A series of ortho‐(aminomethyl)phenylboronic acids was synthesized and their structures were determined by single‐crystal X‐ray diffraction. The structures are stabilized by the inter‐ and intramolecular hydrogen bonds. The sugar‐binding ability of these compounds was evaluated for D ‐glucose, D ‐fructose and D ‐galactose by the competition assay with Alizarin Red S (ARS). The results indicate that the sugar binding ability and selectivity towards sugars depend on the substituents in amino group. Copyright © 2008 John Wiley & Sons, Ltd.