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Computer‐Guided Design in Molecular Recognition: Design and Synthesis of a Glucopyranose Receptor
Author(s) -
Yang Wei,
He Huan,
Drueckhammer Dale G.
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20010504)40:9<1714::aid-anie17140>3.0.co;2-f
Subject(s) - boronic acid , chemistry , receptor , galactose , selectivity , mannose , molecular recognition , fructose , fluorescence , biochemistry , stereochemistry , combinatorial chemistry , molecule , organic chemistry , physics , quantum mechanics , catalysis
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.