Cyclobutane-based peptides/terpyridine conjugates

Two new conjugates, hcptpyDP and hcptpyTP, of a terpyridine derivative incorporating artificial peptide moieties, have been synthesized and their use in the preparation of metal catalysts and organogelators has been investigated. Ru(II) complexes derived from these ligands showed electrochemical beh...

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Detalles Bibliográficos
Autores: Porcar Tost, Oriol, Pi i Boleda, Bernat|||0000-0003-1050-6788, García-Antón, Jordi|||0000-0002-2401-0401, Illa, Ona|||0000-0001-7390-4893, Ortuño Mingarro, Rosa María|||0000-0001-7635-7354
Tipo de recurso: artículo
Fecha de publicación:2018
País:España
Institución:Universitat Autònoma de Barcelona
Repositorio:Dipòsit Digital de Documents de la UAB
Idioma:inglés
OAI Identifier:oai:ddd.uab.cat:274081
Acceso en línea:https://ddd.uab.cat/record/274081
https://dx.doi.org/urn:doi:10.1016/j.tet.2018.10.064
Access Level:acceso abierto
Palabra clave:Cyclobutane-based peptides
Functional organogelators
Metal catalysis
Ruthenium complexes
Terpyridine conjugates
Descripción
Sumario:Two new conjugates, hcptpyDP and hcptpyTP, of a terpyridine derivative incorporating artificial peptide moieties, have been synthesized and their use in the preparation of metal catalysts and organogelators has been investigated. Ru(II) complexes derived from these ligands showed electrochemical behavior and activity as catalysts in the epoxidation of olefins similar to that of Beller's catalyst. As organogelators, these conjugates were able to gelate a variety of solvents, from toluene to methanol, with satisfactory mgc (minimum gelation concentration) values. The presence of 4'-(4-carboxy)phenylterpyridine (hcptpy) moiety allows tuning the gelling properties and also influences the supramolecular self-assembling mode to produce chiral aggregates with respect to parent peptides DP and TP. In the case of the conjugates, π-π interactions provided by the aromatic moieties cooperate with inter-molecular hydrogen bonding between NH and CO in the amide groups. Further properties of peptide/terpyridine conjugates are under investigation in view of future applications.