Chitinase Inhibition by Chitobiose and Chitotriose Thiazolines (pages 2599–2602)
James M. Macdonald, Chris A. Tarling, Edward J. Taylor, Rebecca J. Dennis, David S. Myers, Spencer Knapp, Gideon J. Davies and Stephen G. Withers
Article first published online: 5 MAR 2010 | DOI: 10.1002/anie.200906644
A good imitation: Di- and trisaccharide analogues of the oxazoline intermediate formed during enzymatic hydrolysis of chitin were found to be potent inhibitors of chitinase A. The high affinity and enzymatic stability of a readily synthesized thioamide trisaccharide (two molecules of which are shown in the enzyme active site), and the mechanism-based mode of inhibition, make this analogue a promising candidate for broad-spectrum chitinase inhibition.