title: Efficient synthesis of cysteine-rich cyclic peptides through intramolecular native chemical ligation of N-Hnb-Cys peptide crypto-thioesters.
abstract: We herein introduce a straightforward synthetic route to cysteine-containing cyclic peptides based on the intramolecular native chemical ligation of in situ generated thioesters. Key precursors are N-Hnb-Cys crypto-thioesters, easily synthesized by Fmoc-based SPPS. The strategy is applied to a representative range of naturally occurring cyclic disulfide-rich peptide sequences.
authors.affiliation: Centre de Biophysique Moléculaire, CNRS UPR 4301, Rue Charles Sadron, 45071 Orléans Cedex 2, France. aucagne@cnrs-orleans.fr.
authors.forename: Victor P
authors.initials: VP
authors.lastname: Terrier
authors.affiliation: Centre de Biophysique Moléculaire, CNRS UPR 4301, Rue Charles Sadron, 45071 Orléans Cedex 2, France. aucagne@cnrs-orleans.fr.
authors.forename: Agnès F
authors.initials: AF
authors.lastname: Delmas
authors.affiliation: Centre de Biophysique Moléculaire, CNRS UPR 4301, Rue Charles Sadron, 45071 Orléans Cedex 2, France. aucagne@cnrs-orleans.fr.
authors.forename: Vincent
authors.initials: V
authors.lastname: Aucagne
mesh_terms: D003545:Cysteine / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D008968:Molecular Conformation; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D004952:Esters; D010456:Peptides, Cyclic; D013438:Sulfhydryl Compounds; D003545:Cysteine