title: Peptide and peptide library cyclization via bromomethylbenzene derivatives.
abstract: Cyclization confers several advantages to peptides, cumulatively serving to make them more drug-like. In this protocol, cyclic peptides are generated via bis-alkylation of cysteine-containing peptides using α,α'-dibromo-m-xylene. The reactions are robust and high yielding. Multiple reaction platforms for the application of this versatile strategy are described herein: the cyclization of solid-phase-synthesized peptides, both in solution and on resin, as well as the cyclization of in vitro translated mRNA-peptide fusion libraries on oligo(dT) resin.
authors.affiliation: Department of Chemistry and Massey Cancer Center, Virginia Commonwealth University, 401 College Street, Richmond, VA, 23298-0037, USA.
authors.forename: David E
authors.initials: DE
authors.lastname: Hacker
authors.forename: Mohammed
authors.initials: M
authors.lastname: Almohaini
authors.forename: Aruna
authors.initials: A
authors.lastname: Anbazhagan
authors.forename: Zhong
authors.initials: Z
authors.lastname: Ma
authors.forename: Matthew C T
authors.initials: MC
authors.lastname: Hartman
mesh_terms: D000818:Animals; D006801:Humans; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000737:chemistry; D019151:Peptide Library; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D014176:Protein Biosynthesis; D012333:RNA, Messenger / Q000737:chemistry; D014992:Xylenes / Q000737:chemistry*
chemical_list: D006842:Hydrocarbons, Brominated; D009838:Oligodeoxyribonucleotides; D019151:Peptide Library; D010456:Peptides, Cyclic; D012333:RNA, Messenger; D014992:Xylenes; C027903:oligo (dT)