title: Pyrrolidinone-modified di- and tripeptides: highly diastereoselective preparation and investigation of their stability.
abstract: Pyrrolidine-2,4-diones have been identified as a novel starting point for the synthesis of peptide analogues. This paper describes a method for the efficient and diastereoselective incorporation of this moiety into peptide chains to furnish di- and tripeptide analogs. The stability of these pyrrolidinone modified di- and tripeptides was found to be markedly improved when compared to that of a natural peptide. In addition, solid phase peptide synthesis employing a pyrrolidinone containing tripeptide is demonstrated.
authors.affiliation: Department of Chemistry, Technical University of Denmark, Building 201, DK-2800, Kgs Lyngby, Denmark.
authors.forename: Masood
authors.initials: M
authors.lastname: Hosseini
authors.forename: David
authors.initials: D
authors.lastname: Tanner
authors.forename: Anthony
authors.initials: A
authors.lastname: Murray
authors.forename: Janne E
authors.initials: JE
authors.lastname: Tønder
mesh_terms: D004355:Drug Stability; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D011487:Protein Conformation; D011760:Pyrrolidinones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009842:Oligopeptides; D011760:Pyrrolidinones