title: Bike peptides: a ride through the membrane.
abstract: Several natural peptides have a biaryl or biaryl ether motif in their biologically active structures. A model bicyclic pentapeptide containing a biaryl bridge has been synthesized by solid-phase peptide synthesis combining on-resin Suzuki and Miyaura cross-coupling reactions. Its biological properties in terms of permeability, stability and cytotoxicity have been studied, demonstrating the positive contribution of the biaryl bridge, excellent membrane penetration and serum stability Copyright © 2017 European Peptide Society and John Wiley & Sons, Ltd.
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona), Barcelona Institute of Science and Technology (BIST), 08028, Barcelona, Spain.
authors.forename: Júlia
authors.initials: J
authors.lastname: García-Pindado
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona), Barcelona Institute of Science and Technology (BIST), 08028, Barcelona, Spain.
authors.forename: Soledad
authors.initials: S
authors.lastname: Royo
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona), Barcelona Institute of Science and Technology (BIST), 08028, Barcelona, Spain.
authors.forename: Meritxell
authors.initials: M
authors.lastname: Teixidó
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona), Barcelona Institute of Science and Technology (BIST), 08028, Barcelona, Spain.|Department of Organic Chemistry, University of Barcelona, 08028, Barcelona, Spain.
authors.forename: Ernest
authors.identifier: http://orcid.org/0000-0001-8381-1797
authors.initials: E
authors.lastname: Giralt
mesh_terms: D001688:Biological Products / Q000097:blood / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D006367:HeLa Cells; D006801:Humans; D008968:Molecular Conformation; D009842:Oligopeptides / Q000097:blood / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D060327:Solid-Phase Synthesis Techniques; D013329:Structure-Activity Relationship
chemical_list: D001688:Biological Products; D009842:Oligopeptides
keywords: PAMPA; Suzuki cross-coupling; biostability; borylation; head-to-tail cyclization; solid-phase peptide synthesis; stapled peptides