Cyclobutane-based peptides/terpyridine conjugates : Their use in metal catalysis and as functional organogelators
Porcar Tost, Oriol (Universitat Autònoma de Barcelona. Departament de Química)
Pi i Boleda, Bernat (Universitat Autònoma de Barcelona. Departament de Química)
García-Antón, Jordi (Universitat Autònoma de Barcelona. Departament de Química)
Illa, Ona (Universitat Autònoma de Barcelona. Departament de Química)
Ortuño Mingarro, Rosa María (Universitat Autònoma de Barcelona. Departament de Química)

Date:	2018
Abstract:	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.
Grants:	Agencia Estatal de Investigación CTQ2016-77978-R
Rights:	Aquest document està subjecte a una llicència d'ús Creative Commons. Es permet la reproducció total o parcial, la distribució, i la comunicació pública de l'obra, sempre que no sigui amb finalitats comercials, i sempre que es reconegui l'autoria de l'obra original. No es permet la creació d'obres derivades.
Language:	Anglès
Document:	Article ; recerca ; Versió acceptada per publicar
Subject:	Cyclobutane-based peptides ; Functional organogelators ; Metal catalysis ; Ruthenium complexes ; Terpyridine conjugates
Published in:	Tetrahedron, Vol. 74, Issue 51 (December 2018) , p. 7252-7260, ISSN 1464-5416

DOI: 10.1016/j.tet.2018.10.064

Postprint 31 p, 1.2 MB

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Research literature > UAB research groups literature > Research Centres and Groups (research output) > Experimental sciences > Synthesis of Bioactive Organic Compounds and Functional Materials (SynOrgFUN)
Articles > Research articles
Articles > Published articles