Molecular Recognition of Carbohydrates with Artificial Receptors: Mimicking the Binding Motifs Found in the Crystal Structures of Protein−Carbohydrate Complexes

The binding motifs found in the crystal structures of protein−carbohydrate complexes have been successfully mimicked with simple acyclic pyridine- and pyrimidine-based receptors. A full discussion of the recognition motifs observed in the crystal structures of complexes of receptors 1 and 3 with glucopyranosides 4a and 4b is provided. A remarkable similarity of these motifs to those observed in the crystal structures of sugar-binding proteins and those found by molecular modeling is shown. In addition, the recognition properties of the new pyrimidine receptor 3 toward monosaccharides 4−6 are described. This molecule has been established as a highly effective receptor for β-glucopyranosides.