Thiirancarboxamides as inhibitors of papain.
Derivatives of the thiirancarboxylic acid building-block containing a peptide bond were synthesised and screened against the model cysteine protease papain. The most active of the series showed a second-order rate constant of inactivation comparable to that of the parent compound. The insertion of a peptide moiety seems to compensate the lack of a free carboxylate interacting with the histidinium ion at the enzyme's active site.
Bruno
Gemma
G
Department of Chemistry and Pharmacy, Institute of Pharmacy and Food Chemistry, Wuerzburg, Germany.
Schirmeister
Tanja
T
D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010206:Papain / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship
D002264:Carboxylic Acids; D004791:Enzyme Inhibitors; D010206:Papain