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Chitinase Inhibition by Chitobiose and Chitotriose Thiazolines
Author(s) -
Macdonald James M.,
Tarling Chris A.,
Taylor Edward J.,
Dennis Rebecca J.,
Myers David S.,
Knapp Spencer,
Davies Gideon J.,
Withers Stephen G.
Publication year - 2010
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/anie.200906644
Subject(s) - chitobiose , chitinase , chemistry , trisaccharide , chitin , enzyme , stereochemistry , enzymatic hydrolysis , oxazoline , hydrolysis , biochemistry , combinatorial chemistry , chitosan , catalysis
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.
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