title: Native chemical ligation,thiol-ene click: a methodology for the synthesis of functionalized peptides.
abstract: The sequential combination of native chemical ligation and thiol-ene radical chemistry (NCL-TEC) on the resulting cysteine thiol has been investigated as a methodology for rapidly accessing functionalized peptides. Three sequential cycles of native chemical ligation and subsequent thiyl radical reactions (including a free-radical-mediated desulfurization reaction) were carried out on a peptide backbone demonstrating the iterative nature of this process. The versatility of the thiyl radical reaction at cysteine was demonstrated through the introduction of a number of different side chains including an amino acid derivative, a carbohydrate group, and an alkyl azide. Conditions were developed that allowed the sequential NCL-TEC process to proceed in high yield.
authors.affiliation: Trinity Biomedical Sciences Institute, Trinity College, 152-160 Pearse Street, Dublin 2, Ireland.
authors.forename: Lyn
authors.initials: L
authors.lastname: Markey
authors.forename: Silvia
authors.initials: S
authors.lastname: Giordani
authors.forename: Eoin M
authors.initials: EM
authors.lastname: Scanlan
mesh_terms: D002241:Carbohydrates / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D003545:Cysteine / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D008956:Models, Chemical; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D005609:Free Radicals; D006020:Glycopeptides; D013438:Sulfhydryl Compounds; D003545:Cysteine