Model studies towards carbohydrate–base pair recognition. Relevance of hydrogen–bonding cooperativity

Abstract

The importance of intramolecular OH···OH hydrogen-bonds (H-bonds) in the effective molecular recognition of carbohydrates is highlighted; specifically, the 1,3-cis-diaxial H-bonded OH groups of 1 are shown to provide an efficient binding motif for bidentate coordination of the amino-carbonyl Hoogsteen site of the CG base-pair through the formation of two cooperative intermolecular H-bonds; this result suggests that intramolecularly H-bonded carbohydrate OH groups may be considered as multidentate units able to H-bond cooperatively.