title: Protecting group variations of delta-mercaptolysine useful in chemical ubiquitylation.
abstract: The high efficiency and chemoselectivity of peptide ubiquitylation that is achieved using the delta-mercaptolysine prompted us to expand the scope of this residue in various ligation schemes. In this report, we demonstrate the synthesis of five analogues of this important amino acid bearing a variety of protecting groups, which is essential in sequential peptide ligation and ubiquitylation. The key-step in the synthesis is the nucleophilic 1,4-addition of a variety of thiols on a nitro olefin scaffold.
authors.affiliation: Department of Chemistry, Ben-Gurion University of the Negev, Beer Sheva 84105, Israel.
authors.forename: Mahmood
authors.initials: M
authors.lastname: Haj-Yahya
authors.forename: K S
authors.initials: KS
authors.lastname: Ajish Kumar
authors.forename: Lesly A
authors.initials: LA
authors.lastname: Erlich
authors.forename: Ashraf
authors.initials: A
authors.lastname: Brik
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D000818:Animals; D006801:Humans; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D054875:Ubiquitination
chemical_list: D000596:Amino Acids; D010455:Peptides