title: Macrocyclic templates for library synthesis of peptido-conjugates.
abstract: Cyclic peptides have wide utility in the biological sciences. As conformationally locked analogs of the parent linear peptides, they possess greater stability under physiological conditions and increased binding affinity for their targets. As investigations of biological processes often require reporter molecules and functional readouts, chemical probes are commonly appended with functional groups that allow for conjugation to biological entities. Herein we describe the functionalization of cyclic peptides prepared via aziridine aldehyde-mediated macrocyclization. These cyclic peptides contain an aziridine ring that can be further functionalized by ring opening with nucleophiles. We report on the methodology used to produce a cyclic peptide analog of Pro-Gly-Leu-Gly-Phe with either azido or sulfhydryl functionality.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, Canada, M5S 3H6.
authors.forename: Serge
authors.initials: S
authors.lastname: Zaretsky
authors.forename: Joanne
authors.initials: J
authors.lastname: Tan
authors.forename: Jennifer L
authors.initials: JL
authors.lastname: Hickey
authors.forename: Andrei K
authors.initials: AK
authors.lastname: Yudin
mesh_terms: D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D019151:Peptide Library; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D009842:Oligopeptides; D019151:Peptide Library; D010456:Peptides, Cyclic