243143-24-0Relevant academic research and scientific papers
1-Alkoxycarbonyl-3-bromoazetidin-2-ones as potential elastase inhibitors
Beauve, Cecile,Tjoens, Gregory,Touillaux, Roland,Lamotte-Brasseur, Josette,Marchand-Brynaert, Jacqueline,Fastrez, Jacques
, p. 1441 - 1447 (1999)
Three 1-alkoxycarbonyl-3-bromoazetidin-2-ones have been prepared by reaction of (3S)-3-(tert-butoxycarbonyl)amino-azetidin-2-one with benzyl, trichloroethyl, and trifluoroethyl chloroformates followed by tBoc deprotection, diazotation of the exocyclic amino function and its substitution with potassium bromide. The 3-bromoazetidin-2-ones were obtained as racemic mixtures. Their hydroxide-catalyzed hydrolysis exclusively affords ring-opening products. Porcine pancreatic elastase (PPE) catalyzes the same reaction stereospecifically. Model building suggests that it is the (R) isomer that is enzymatically hydrolysed. The PPE-catalyzed hydrolysis is characterised by low k(cat) and K(m) values. Accordingly, these compounds behave as transient inhibitors of the enzyme.
