Molecular recognition of carbohydrates with acyclic pyridine-based receptors.

The recognition capabilities of acyclic pyridine-based receptors toward monosaccharides were evaluated. Aminopyridine receptors based on the 2,4,6-trimethyl- or 2,4,6-triethylbenzene frame show high beta vs alpha binding selectivity in the recognition of glucopyranosides. Amidopyridine receptors, which are sterically less hindered at nitrogen, display high efficiency and an inverse selectivity.

High alpha/beta-anomer selectivity in molecular recognition of carbohydrates by artificial receptors.

[structure: see text] New effective, acyclic, pyridine-based receptors 1-3 show remarkable alpha/beta binding selectivity in the recognition of monosaccharides. They are able to participate in cooperative and bidentate hydrogen bonds with sugar hydroxyls as well as in CH-pi interactions with CH's of sugar molecules.