Protein Science

Peptidyl cyclopropenones: Reversible inhibitors, irreversible inhibitors, or substrates of cysteine proteases?

M Cohen, U Bretler, A Albeck

Index: Cohen, Meital; Bretler, Uriel; Albeck, Amnon Protein Science, 2013 , vol. 22, # 6 p. 788 - 799

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Abstract

Abstract Peptidyl cyclopropenones were previously introduced as selective cysteine protease reversible inhibitors. In the present study we synthesized one such peptidyl cyclopropenone and investigated its interaction with papain, a prototype cysteine protease. A set of kinetics, biochemical, HPLC, MS, and 13 C-NMR experiments revealed that the peptidyl cyclopropenone was an irreversible inhibitor of the enzyme, alkylating the ...