title: Acid-catalyzed tandem thiol switch for preparing peptide thioesters from mercaptoethyl esters.
abstract: An efficient method compatible with Fmoc synthesis for preparing peptide thioesters via an acid-catalyzed tandem "thiol switch" of esters is described first by an intramolecular O-S acyl shift and then by an intermolecular S-S exchange, with concurrent deblocking of side chain protection groups.
authors.affiliation: School of Biological Sciences, Nanyang Technological University, Singapore.
authors.forename: Khee Dong
authors.initials: KD
authors.lastname: Eom
authors.forename: James P
authors.initials: JP
authors.lastname: Tam
mesh_terms: D002384:Catalysis; D004952:Esters; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D004952:Esters; D010455:Peptides; D013438:Sulfhydryl Compounds