Journal of Organic Chemistry 2013-09-20

Artificial receptors inspired by crystal structures of complexes formed between acyclic receptors and monosaccharides: design, syntheses, and binding properties.

Jan Lippe, Monika Mazik

Index: J. Org. Chem. 78(18) , 9013-20, (2013)

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Abstract

The binding motifs found in the crystal structures of complexes formed between artificial receptors and monosaccharides, reported previously by our group, have inspired us to design new macrocyclic and acyclic receptors, which were expected to form strong 1:1 complexes with monosaccharides, in particular with β-glucosides, through participation in the formation of CH-π interactions and hydrogen bonds with the sugar substrate. As first representatives of these compounds we have prepared the macrocycles 8-12 and the acyclic molecules 13-16, incorporating two central triethylbenzene units. The new compounds had been designed to bind monosaccharides via interactions of both central benzene rings with the sugar CH groups. Initial binding studies have confirmed the expected favorable binding capabilities of the macrocyclic compounds and indicated interesting binding properties of the acyclic analogues.