title: Synthesis of thiazolidine thioester peptides and acceleration of native chemical ligation.
abstract: Thiazolidine thioester peptides were synthesized by reacting bis(2-sulfanylethyl)amido peptides with glyoxylic acid at pH 1. A significant increase in Native Chemical Ligation (NCL) rate was observed with thiazolidine thioesters compared to 3-mercaptopropionic acid-thioester analogues. The method is of particular interest for accelerating valine-cysteine peptide bond formation.
authors.affiliation: CNRS UMR 8161, Univ Lille Nord de France, Institut Pasteur de Lille, IFR 142 Molecular and Cellular Medicine, 1 rue du Pr Calmette 59021 Lille Cedex, France.
authors.forename: Julien
authors.initials: J
authors.lastname: Dheur
authors.forename: Nathalie
authors.initials: N
authors.lastname: Ollivier
authors.forename: Oleg
authors.initials: O
authors.lastname: Melnyk
mesh_terms: D015097:3-Mercaptopropionic Acid / Q000031:analogs & derivatives / Q000737:chemistry; D003545:Cysteine / Q000737:chemistry; D004952:Esters; D006038:Glyoxylates / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D053778:Thiazolidines / Q000138:chemical synthesis* / Q000737:chemistry; D014633:Valine / Q000737:chemistry
chemical_list: D004952:Esters; D006038:Glyoxylates; D010455:Peptides; D053778:Thiazolidines; D015097:3-Mercaptopropionic Acid; D014633:Valine; C031150:glyoxylic acid; D003545:Cysteine