Computer-Guided Design in Molecular Recognition: Design and Synthesis of a Glucopyranose Receptor

Abstract

Greater than 400-fold selectivity for glucose over galactose, mannose, and fructose has been achieved with a receptor designed by the computer program CAVEAT. The receptor has precisely positioned boronic acid groups for cyclic boronate formation with the 1,2- and 4,6-hydroxy groups of α-D-glucopyranose (see picture) and exhibits a 50 % decrease in fluorescence upon glucose binding.