Bike peptides: a ride through the membrane

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 properti...

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Detalhes bibliográficos
Autores: García Pindado, Júlia, Royo, Soledad, Teixidó Turà, Meritxell, Giralt Lledó, Ernest
Formato: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2017
País:España
Recursos:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/110580
Acesso em linha:https://hdl.handle.net/2445/110580
Access Level:acceso abierto
Palavra-chave:Síntesi de pèptids
Productes naturals
Síntesi orgànica
Peptide synthesis
Natural products
Organic synthesis
Descrição
Resumo: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, demon-strating the positive contribution of the biaryl bridge, excellent membrane penetration and serum stability