title: Synthesis of stapled beta3-peptides through ring-closing metathesis.
abstract: The first synthesis of carbon-stapled beta(3)-peptides is reported. The precursor beta(3)-peptides, with O-allyl beta-serines located in an i/i+3 relationship, were prepared on solid phase. We show that efficient ring-closing metathesis (RCM) of these new beta(3)-peptides proceeds smoothly either in solution or on an appropriate solid support. All products were generated with high selectivity for the E-isomer.
authors.affiliation: School of Chemistry, Monash University, Clayton 3800 Victoria, Australia.
authors.forename: Ylva E
authors.initials: YE
authors.lastname: Bergman
authors.forename: Mark P
authors.initials: MP
authors.lastname: Del Borgo
authors.forename: Romila D
authors.initials: RD
authors.lastname: Gopalan
authors.forename: Sania
authors.initials: S
authors.lastname: Jalal
authors.forename: Sharon E
authors.initials: SE
authors.lastname: Unabia
authors.forename: Marisa
authors.initials: M
authors.lastname: Ciampini
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Clayton
authors.forename: Jordan M
authors.initials: JM
authors.lastname: Fletcher
authors.forename: Roger J
authors.initials: RJ
authors.lastname: Mulder
authors.forename: Jacqueline A
authors.initials: JA
authors.lastname: Wilce
authors.forename: Marie-Isabel
authors.initials: MI
authors.lastname: Aguilar
authors.forename: Patrick
authors.initials: P
authors.lastname: Perlmutter
mesh_terms: D003500:Cyclization; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011487:Protein Conformation; D017433:Protein Structure, Secondary
chemical_list: D010455:Peptides