From sensing to catalysis: Tapping boron's affinity for diols and α-hydroxyacids

Abstract

Bis(boronic acids) have been widely used in the development of chemosensors for sugars, most importantly glucose. We have previously reported that bis(boronates) have an even higher affinity for bis(α-hydroxycarboxylates) such as tartrate than for simple bis(diols) like erythritol.[1] We will look at the design of novel boronate-based receptors for α-hydroxyacids and inositols[2], an important class of cell-signalling molecules. The affinity of boric and boronic acids for α-hydroxycarboxylates has also been shown to catalyze esterification of these species and this reaction is applicable to carbohydrates.