title: Synthesis of thioester peptides for the incorporation of thioamides into proteins by native chemical ligation.
abstract: Thioamides can be used as photoswitches, as reporters of local environment, as inhibitors of enzymes, and as fluorescence quenchers. We have recently demonstrated the incorporation of thioamides into polypeptides and proteins using native chemical ligation (NCL). In this protocol, we describe procedures for the synthesis of a thioamide precursor and an NCL-ready thioamide-containing peptide using Dawson's N-acyl-benzimidazolinone (Nbz) process. We include a description of the synthesis by NCL of a thioamide-labeled fragment of the neuronal protein α-synuclein.
authors.affiliation: Department of Chemistry, University of Pennsylvania, Philadelphia, PA, USA.
authors.forename: Solongo
authors.initials: S
authors.lastname: Batjargal
authors.affiliation: Department of Chemistry, University of Pennsylvania, Philadelphia, PA, USA.
authors.forename: Yun
authors.initials: Y
authors.lastname: Huang
authors.affiliation: Department of Chemistry, University of Pennsylvania, Philadelphia, PA, USA.
authors.forename: Yanxin J
authors.initials: YJ
authors.lastname: Wang
authors.affiliation: Department of Chemistry, University of Pennsylvania, Philadelphia, PA, USA.
authors.forename: E James
authors.initials: EJ
authors.lastname: Petersson
mesh_terms: D000215:Acylation; D060326:Chemistry Techniques, Synthetic; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis*; D011506:Proteins / Q000138:chemical synthesis* / Q000737:chemistry; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry; D013854:Thioamides / Q000737:chemistry*
chemical_list: D010455:Peptides; D011506:Proteins; D013440:Sulfides; D013854:Thioamides
keywords: Fmoc SPPS; Native Chemical Ligation; Thioamide; Thioester