title: Direct on-resin synthesis of peptide-alphathiophenylesters for use in native chemical ligation.
abstract: [reaction: see text] A peptide-(alpha)thiophenylester is a key reactant in native chemical ligation. Preformation of the peptide-(alpha)thiophenylester could be useful for enhancing the ligation reaction. We report the direct on-resin preparation of preformed peptide-(alpha)thiophenylesters using a simple and efficient method. The peptide-(alpha)thiophenylester reacted extremely rapidly with a Cys-peptide when compared to the peptide-(alpha)thioalkylester.
authors.affiliation: Institute for Biophysical Dynamics, Department of Chemistry, The University of Chicago, Chicago, Illinois 60637, USA.
authors.forename: Duhee
authors.initials: D
authors.lastname: Bang
authors.forename: Brad L
authors.initials: BL
authors.lastname: Pentelute
authors.forename: Zachary P
authors.initials: ZP
authors.lastname: Gates
authors.forename: Stephen B
authors.initials: SB
authors.lastname: Kent
mesh_terms: D000595:Amino Acid Sequence; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters; D008958:Models, Molecular; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013816:Thermodynamics
chemical_list: D001555:Benzene Derivatives; D004952:Esters; D010455:Peptides