title: Fmoc solid-phase synthesis of peptide thioesters using an intramolecularn,S-acyl shift.
abstract: [reaction: see text] We describe the Fmoc solid-phase synthesis of peptide thioesters based on the alkylation of the safety-catch sulfonamide linker with a protected 2-mercaptoethanol derivative. The thioester is generated on the solid phase after the peptide chain assembly as a consequence of an intramolecular N,S-acyl shift. Depending on the stability of the spacer separating the sulfonamide linker from the resin toward TFA, treatment of the peptidyl resin with TFA led to a soluble or supported deprotected thioester.
authors.affiliation: Institut Pasteur de Lille, Université de Lille 2, UMR 8525 CNRS, 1 rue du Professeur Calmette, 59021 Lille Cedex, France.
authors.forename: Nathalie
authors.initials: N
authors.lastname: Ollivier
authors.forename: Jean-Bernard
authors.initials: JB
authors.lastname: Behr
authors.forename: Ouafâa
authors.initials: O
authors.lastname: El-Mahdi
authors.forename: Annick
authors.initials: A
authors.lastname: Blanpain
authors.forename: Oleg
authors.initials: O
authors.lastname: Melnyk
mesh_terms: D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D000596:Amino Acids; D004952:Esters; D010455:Peptides