title: Amine capture strategy for peptide bond formation by means of quinolinium thioester salts.
abstract: A new and unprecedented exploitation of quinolinium thioester salts 2 in peptide bond formation is reported. These synthetic tools were assessed during the preparation of a number of dipeptides 3a-f obtained in good yields with complete stereochemical integrity. A sequential mechanism related to a prior amine capture strategy is well-established. Additionally, a tripeptide 3g was prepared according to a "safety-catch" approach, thus demonstrating the important potential of these new synthetic tools in the design of new safety-catch linkers exploitable in Solid-Phase Peptide Synthesis (SPPS).
authors.affiliation: Laboratoire de Chimie Organique Fine et Hétérocyclique UMR 6014 IRCOF, CNRS, Université et INSA de Rouen, B.P 08, F-76131 Mont-Saint-Aignan Cédex, France.
authors.forename: Stéphane
authors.initials: S
authors.lastname: Leleu
authors.forename: Maël
authors.initials: M
authors.lastname: Penhoat
authors.forename: Alexis
authors.initials: A
authors.lastname: Bouet
authors.forename: Georges
authors.initials: G
authors.lastname: Dupas
authors.forename: Cyril
authors.initials: C
authors.lastname: Papamicaël
authors.forename: Francis
authors.initials: F
authors.lastname: Marsais
authors.forename: Vincent
authors.initials: V
authors.lastname: Levacher
mesh_terms: D000588:Amines / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis*; D011806:Quinolinium Compounds / Q000737:chemistry*; D012492:Salts / Q000737:chemistry; D013463:Sulfuric Acid Esters / Q000737:chemistry*
chemical_list: D000588:Amines; D010455:Peptides; D011806:Quinolinium Compounds; D012492:Salts; D013463:Sulfuric Acid Esters