title: Acceleration of thiol additive-free native chemical ligation by intramolecular S → S acyl transfer.
abstract: Peptide-mercaptopropionylcysteine (MPA-Cys) thioesters show a surprisingly high reactivity in native chemical ligation (NCL) and allow thiol-additive free reactions. This facilitates sequential NCL reactions and ligation-desulfurization reactions in one-pot formats. The synthetic utility is demonstrated by the synthesis of a SH3 domain.
authors.affiliation: Humboldt-Universität zu Berlin, Institut für Chemie, Brook-Taylor-Str. 2, 12489 Berlin, Germany. oliver.seitz@chemie.hu-berlin.de.
authors.forename: J
authors.initials: J
authors.lastname: Schmalisch
authors.forename: O
authors.initials: O
authors.lastname: Seitz
mesh_terms: D000595:Amino Acid Sequence; D003545:Cysteine / Q000737:chemistry*; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D018909:src Homology Domains
chemical_list: D010455:Peptides; D013438:Sulfhydryl Compounds; D003545:Cysteine