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• W2082416611 endingPage "1291" @default.
• W2082416611 startingPage "1281" @default.
• W2082416611 abstract "Peptides containing aziridine-2,3-dicarboxylate (Azi) as electrophilic building block are evaluated as inhibitors of the cysteine proteases papain, cathepsin B, cathepsin L and clostripain. The influence of a free carboxylic acid as functional group at different positions of the inhibitor molecule on inhibition is analyzed. Structure-activity relationships and binding mode hypotheses are discussed. In contrast to the bacterial enzyme clostripain, the papain like mammalian proteases (cathepsins) are irreversibly inactivated by aziridinyl peptides. N-Unsubstituted aziridines are much more potent inhibitors of papain and cathepsins if they contain the free carboxylic acid attached to the aziridine ring (HOAzi-Leu-ProOBzl). Two free carboxylic acid functions at the aziridine ring are necessary for good inhibition of these enzymes by N-acylated aziridinyl peptides (BOC-Phe-Azi(OH)2). Chimeric bispeptidyl derivatives are selective CB inhibitors if the free acid is located at the C-terminus of the peptide (BOC-Phe-(EtO)Azi-Leu-ProOH). Clostripain is only inhibited by aziridinyl peptide esters." @default.
• W2082416611 created "2016-06-24" @default.
• W2082416611 creator A5007805486 @default.
• W2082416611 creator A5076430638 @default.
• W2082416611 date "2000-06-01" @default.
• W2082416611 modified "2023-10-03" @default.
• W2082416611 title "aziridinyl peptides as inhibitors of cysteine proteases: Effect of a free carboxylic acid function on inhibition" @default.
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• W2082416611 doi "https://doi.org/10.1016/s0968-0896(00)00058-4" @default.
• W2082416611 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/10896108" @default.
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