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.
Keywords: PAMPA; Suzuki cross-coupling; biostability; borylation; head-to-tail cyclization; solid-phase peptide synthesis; stapled peptides.
Copyright © 2017 European Peptide Society and John Wiley & Sons, Ltd.