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Hydrolysis of Amides Catalyzed by 4‐Heterocyclohexanones: Small Molecule Mimics of Serine Proteases
Author(s) -
Ghosh Mousumi,
Conroy Jeffrey L.,
Seto Christopher T.
Publication year - 1999
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/(sici)1521-3773(19990215)38:4<514::aid-anie514>3.0.co;2-j
Subject(s) - amide , catalysis , chemistry , proteases , hydrolysis , serine , substituent , substrate (aquarium) , molecule , combinatorial chemistry , organic chemistry , stereochemistry , enzyme , oceanography , geology
The base‐promoted hydrolysis of amide substrates that contain a thiol substituent in the position α to the amide carbonyl group is effectively catalyzed by 4‐heterocyclohexanones [Eq. (1)]. The proposed mechanism of the hydrolysis reaction mimics that employed by serine proteases, and involves equilibrium binding of the substrate to the catalyst, formation of an acyl‐catalyst intermediate, and deacylation of the intermediate to release the product and regenerate the catalyst.