Abstract
Cbz-Phe-epoxide was designed as a selective inactivator of cysteine proteases. It exhibits a time- and concentration-dependent inactivation of cysteine proteases, while showing no activity towards serine proteases. The inhibition is irreversible, correlated with loss of the free active-site thiol, and its rate is at least 10 4 faster than the rate of a model reaction in solution. These results support the proposed active-site directed, protonation-dependent, mechanism-based mode of inactivation of cysteine proteases by the new inhibitor.
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