Papain inhibitions by optically active E-64 analogs.
Modification of E-64 focused on the terminal agmatine for practical use led to some potent analogs which were successfully obtained by a stereoselective synthesis using D-tartaric acid as a starting material. Ep-475 (id. E-64-c), in which the agmatine was replaced by 3-methyl-butylamine, was found to react with the essential SH of papain in accord with the decrease of activity. [3H]Ep-475 was irreversibly incorporated into papain in an equimolar ratio. None of the analogs showed any effect on thiol enzymes other than proteolytic ones.
D000376:Agmatine / Q000031:analogs & derivatives / Q000494:pharmacology*; D006146:Guanidines / Q000494:pharmacology*; D007700:Kinetics; D007930:Leucine / Q000031:analogs & derivatives* / Q000494:pharmacology; D009904:Optical Rotation; D010206:Papain / Q000494:pharmacology*; D011480:Protease Inhibitors / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D006146:Guanidines; D011480:Protease Inhibitors; D000376:Agmatine; D010206:Papain; D007930:Leucine; C024974:E 64