title: Aspartic protease inhibitors: expedient synthesis of 2-substituted statines.
abstract: [reaction: see text]. General stereocontrolled synthesis of all four (2,3)-stereoisomers of 2-substituted statines is described. The 2,3-syn and 2,3-anti isomers were synthesized via beta-ketoester reduction and aldol reactions, respectively. Peptides containing 2-substituted statines inhibit porcine pepsin with nanomolar IC50 values.
authors.affiliation: Department of Chemistry and School of Pharmacy, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA.
authors.forename: J M
authors.initials: JM
authors.lastname: Travins
authors.forename: M G
authors.initials: MG
authors.lastname: Bursavich
authors.forename: D F
authors.initials: DF
authors.lastname: Veber
authors.forename: D H
authors.initials: DH
authors.lastname: Rich
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D016282:Aspartic Acid Endopeptidases / Q000037:antagonists & inhibitors*; D011480:Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013552:Swine
chemical_list: D000596:Amino Acids; D011480:Protease Inhibitors; D016282:Aspartic Acid Endopeptidases; C013165:statine