Recognition properties of receptors based on dimesitylmethane-derived core: Di- vs. monosaccharide preference

Dimesitylmethane-derived receptors 12 and 13, incorporating four heterocyclic recognition groups capable of serving as hydrogen bonding sites, were designed to recognize disaccharides. It has been shown by H-1 NMR and fluorescence spectroscopic titrations that compounds 12 and 13 display high binding affinities toward alpha- and beta-maltoside, as well as strong di- vs monosaccharide preference in organic media. 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, as indicated by experimental data and molecular modeling calculations.