High-Affinity Disaccharide Binding by Tricyclic Synthetic Lectins

B. Sookcharoenpinyo, E. Klein, Y. Ferrand, D. B. Walker, P.R. Brotherhood, C. Ke, M. P. Crump, A. P. Davis*

Angew. Chem. Int. Ed. 2012, 51, 4586-4590


Stay flexible: Rigid preorganization is not always the best approach to molecular recognition. Unlike previous synthetic lectins, new receptors (see picture) were synthesized that possess conformational freedom which allows hydrophobically driven collapse of the cavity. Nonetheless, they bind their carbohydrate targets in water with ground-breaking affinities (up to 4500 m−1 for methyl cellobioside, R=Me) and selectivities.