N,O-diacylhydroxylamines as enzyme-activated inhibitors for serine proteases

Several N-peptidyl-O(4-nitrobenzoyl)-hydroxylamines were synthesized and their inhibitory action against dipeptidyl-peptidase IV, alpha-chymotrypsin, elastase and thermitase was investigated. If the petidyl residue can be recognized by the enzyme as a substrate, a time dependent irreversible inactivation occurs. The mechanism of inhibition by N,O-diacylhydroxylamines as enzyme activated inhibitors is discussed.