title: Diastereoselective synthesis of alpha,beta'-disubstituted aminomethyl(2-carboxyethyl)phosphinates as phosphinyl dipeptide isosteres.
abstract: A new and efficient method has been developed for the diastereoselective synthesis of unnatural dipeptide analogues containing the metabolically stable phosphinic moiety, NH 2XaaPsi[P(O)OHCH 2]XaaOH, which mimics the transition state of tetrahedral geometry of a scissile peptide bond in hydrolysis by protease. The method is based upon stereospecific Michael addition of stereodefined alpha-aminoalkyl- H-phosphinates to acrylates and subsequent diastereoselective alkylation at the beta'-position of the resulting Michael adducts.
authors.affiliation: School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
authors.forename: Takehiro
authors.initials: T
authors.lastname: Yamagishi
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Ichikawa
authors.forename: Terumitsu
authors.initials: T
authors.lastname: Haruki
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Yokomatsu
mesh_terms: D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D010721:Phosphinic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D004151:Dipeptides; D010721:Phosphinic Acids