Highly effective receptors showing di- vs. monosaccharide preference

Abstract

Receptors 1 and 2, incorporating two heterocyclic recognition units as well as oxime- or hydroxymethyl-based hydrogen-bonding sites, were prepared, and their binding properties toward neutral sugars were determined. The design of these receptors was inspired by the binding motifs observed in the crystal structure of protein–carbohydrate complexes. The receptors 1 and 2 are able to recognize both mono- and disaccharides, with a strong preference for the disaccharides. Both hydrogen-bonding and interactions of the sugar CH's with the phenyl rings of the receptor contribute to the stabilisation of the receptor–sugar complexes. Molecular modeling calculations, synthesis and binding studies are described.