title: Fmoc synthesis of peptide thioesters without post-chain-assembly manipulation.
abstract: An operationally simple method for the synthesis of peptide thioesters is developed using standard Fmoc solid-phase peptide synthesis procedures. The method relies on the use of a premade enamide-containing amino acid which, in the final TFA cleavage step, renders the desired thioester functionality through an irreversible intramolecular N-to-S acyl transfer.
authors.affiliation: Department of Chemistry, Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Tsinghua University, Beijing 100084, China.
authors.forename: Ji-Shen
authors.initials: JS
authors.lastname: Zheng
authors.forename: Hao-Nan
authors.initials: HN
authors.lastname: Chang
authors.forename: Feng-Liang
authors.initials: FL
authors.lastname: Wang
authors.forename: Lei
authors.initials: L
authors.lastname: Liu
mesh_terms: D000595:Amino Acid Sequence; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D002352:Carrier Proteins / Q000138:chemical synthesis; D002625:Chemistry, Organic / Q000379:methods*; D000079922:Copper Transport Proteins; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D006801:Humans; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000596:Amino Acids; C491006:COX17 protein, human; D002352:Carrier Proteins; D000079922:Copper Transport Proteins; D004952:Esters; D010455:Peptides; D013438:Sulfhydryl Compounds