title: Selectively Activatable Latent Thiol and Selenolesters Simplify the Access to Cyclic or Branched Peptide Scaffolds.
abstract: The cyclic dichalcogenides based on the bis(2-chalcogenoethyl)amide structure are latent N,S (SEA, chalcogen = S) or N,Se (SeEA, chalcogen = Se) acyl shift systems. The large difference in the reducing potential between SEA and SeEA dichalcogenides allows their sequential and selective activation by reduction. Based on these concepts, one-pot three or four peptide segment assembly processes were designed, facilitating access to branched or cyclic peptide scaffolds.
authors.affiliation: UMR CNRS 8161 Pasteur Institute of Lille, Univ Lille, 1 rue du Pr Calmette, 59021 Lille, France.
authors.forename: Laurent
authors.initials: L
authors.lastname: Raibaut
authors.affiliation: UMR CNRS 8161 Pasteur Institute of Lille, Univ Lille, 1 rue du Pr Calmette, 59021 Lille, France.
authors.forename: Hervé
authors.initials: H
authors.lastname: Drobecq
authors.affiliation: UMR CNRS 8161 Pasteur Institute of Lille, Univ Lille, 1 rue du Pr Calmette, 59021 Lille, France.
authors.forename: Oleg
authors.initials: O
authors.lastname: Melnyk
mesh_terms: D000577:Amides / Q000737:chemistry*; D018011:Chalcogens / Q000138:chemical synthesis* / Q000737:chemistry; D003545:Cysteine / Q000737:chemistry; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D018011:Chalcogens; D010455:Peptides; D010456:Peptides, Cyclic; C000602349:bis(2-chalcogenoethyl)amide; D003545:Cysteine