Synthesis, hydrolysis, biochemical and theoretical evaluation of 1,4-bis(alkoxycarbonyl)azetidin-2-ones as potential elastase inhibitors

Gérard, Stéphane; Dive, Georges; Clamot, Brigitte; Touillaux, Roland; Marchand-Brynaert, Jacqueline

doi:10.1016/S0040-4020(02)00112-6

Article (Scientific journals)

Synthesis, hydrolysis, biochemical and theoretical evaluation of 1,4-bis(alkoxycarbonyl)azetidin-2-ones as potential elastase inhibitors

Gérard, Stéphane; Dive, Georges; Clamot, Brigitte et al.

2002 • In Tetrahedron, 58 (12), p. 2423-2433

Peer Reviewed verified by ORBi

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https://hdl.handle.net/2268/30029

DOI
10.1016/S0040-4020(02)00112-6

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Keywords :

beta-lactam; serine-protease inhibition; elastase; ab initio calculation

Abstract :

[en] A series of 1,4-bis(alkoxycarbonyl)azetidin-2-ones, designed as potential suicide-inhibitors of serine proteases, has been synthesized and evaluated against porcine pancreatic elastase (PPE). The most active compound (K(i)similar to10 muM; reversible inhibitor) was equipped with phenethyloxycarbonyl and benzyloxycarbonyl side-chains at positions N1 and C4, respectively, with the (S)-configuration. H-1 NMR spectroscopic analysis of the reaction mixtures showed that the ester function is preferentially hydrolyzed, in both chemical and enzyme-catalyzed reactions, with regard to the azetidinone and urethane functions. Considering the three potentially sensitive carbonyl functions and the two stereoisomers, ab initio calculations were performed to determine the energetic barriers required to reach the transition state structures of hydrolysis in a model of the enzyme pocket. (C) 2002 Elsevier Science Ltd. All rights reserved.

Disciplines :

Chemistry

Author, co-author :

Gérard, Stéphane

Dive, Georges ; Université de Liège - ULiège > Centre d'ingénierie des protéines

Clamot, Brigitte

Touillaux, Roland

Marchand-Brynaert, Jacqueline

Language :

English

Title :

Synthesis, hydrolysis, biochemical and theoretical evaluation of 1,4-bis(alkoxycarbonyl)azetidin-2-ones as potential elastase inhibitors

Publication date :

18 March 2002

Journal title :

Tetrahedron

ISSN :

0040-4020

Publisher :

Pergamon-Elsevier Science Ltd, Oxford, United Kingdom

Volume :

Issue :

Pages :

2423-2433

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 28 November 2009

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