Reversible covalent interactions of beta-aminoboronic acids with carbohydrate derivatives

[small beta]-Aminoalkylboronic acids are capable of binding to carbohydrate derivatives through reversible covalent interactions. An anthracene-bearing [small beta]-aminoboronic acid has been synthesized, enabling determinations of association constants for binding of sugars by fluorescence spectroscopy. The diol-binding properties of [small beta]-aminoboronic acids are also useful in catalysis: one such compound displays remarkably high activity for regioselective O-acylation of a pyranoside derivative.