title: A new method for synthesis of peptide thioesters via irreversible N-to-S acyl transfer.
abstract: A new synthetic method for peptide thioesters is described using Fmoc solid-phase peptide synthesis (Fmoc-SPPS). This method employs a novel enamide motif to facilitate irreversible intramolecular N-to-S acyl migration, which can efficiently afford the desired peptide thioesters (3 h, 30 °C) under the final trifluoroacetic acid (TFA) cleavage conditions. The acyl-transfer-mediated approach for synthesis of peptide thioesters tolerated different C-terminal residues and was used to synthesize human C-C motif chemokine 11 (hCCL11) via native chemical ligation.
authors.affiliation: High Magnetic Field Laboratory, Chinese Academy of Sciences , Hefei 230031, China.
authors.forename: Ji-Shen
authors.initials: JS
authors.lastname: Zheng
authors.forename: Xin
authors.initials: X
authors.lastname: Chen
authors.forename: Shan
authors.initials: S
authors.lastname: Tang
authors.forename: Hao-Nan
authors.initials: HN
authors.lastname: Chang
authors.forename: Feng-Liang
authors.initials: FL
authors.lastname: Wang
authors.forename: Chao
authors.initials: C
authors.lastname: Zuo
mesh_terms: D000595:Amino Acid Sequence; D054413:Chemokine CCL11 / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D014269:Trifluoroacetic Acid / Q000737:chemistry
chemical_list: C515456:CCL11 protein, human; D054413:Chemokine CCL11; D009842:Oligopeptides; D013457:Sulfur Compounds; D014269:Trifluoroacetic Acid