title: Synthesis and evaluation of chloromethyl sulfoxides as a new class of selective irreversible cysteine protease inhibitors.
abstract: The synthesis and biological evaluation of a new class of selective irreversible cysteine protease inhibitors is described. A set of amino acid based chloromethyl sulfoxides was prepared and they were found to inhibit irreversibly the cysteine protease papain. They were selective for cysteine proteases since no inhibition was found for the serine protease chymotrypsin.
authors.affiliation: Department of Medicinal Chemistry and Chemical Biology, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, PO Box 80082, NL-3508 TB Utrecht, The Netherlands.
authors.forename: Arwin J
authors.initials: AJ
authors.lastname: Brouwer
authors.forename: Anton
authors.initials: A
authors.lastname: Bunschoten
authors.forename: Rob M J
authors.initials: RM
authors.lastname: Liskamp
mesh_terms: D018360:Crystallography, X-Ray; D015853:Cysteine Proteinase Inhibitors / Q000138:chemical synthesis / Q000145:classification / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D010206:Papain / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013454:Sulfoxides / Q000138:chemical synthesis / Q000145:classification / Q000494:pharmacology
chemical_list: D015853:Cysteine Proteinase Inhibitors; D013454:Sulfoxides; D010206:Papain