Issue 89, 2015

Coordination behaviour of new open chain and macrocyclic peptidomimetic compounds with copper(ii)

Abstract

Two valine-derived bis(amino amides) ligands have been prepared and fully characterized. Both compounds contain additional functionalities that implement their basicity and their water solubility. Besides, compound 1 is an open chain ligand, while 2 is a macrocycle. Their protonation constants as well as their stability constants for the formation of the corresponding Cu2+ complexes have been determined potentiometrically. Important differences are associated to the macrocyclic effect and to the additional functionalities in the spacer. The presence of an additional amine group and/or the inclusion of a carboxylic side chain in this spacer increase the stabilities of the Cu2+complexes, suggesting its participation in the interaction with the metal. Thus, 2 is the first pseudopeptidic cyclophane of this family displaying the ability to form highly stable metal complexes in water. UV-Vis and ESI-MS were used for analyzing the complex species detected in the speciation diagram.

Graphical abstract: Coordination behaviour of new open chain and macrocyclic peptidomimetic compounds with copper(ii)

Supplementary files

Article information

Article type
Paper
Submitted
22 Jun 2015
Accepted
12 Aug 2015
First published
14 Aug 2015

RSC Adv., 2015,5, 72579-72589

Author version available

Coordination behaviour of new open chain and macrocyclic peptidomimetic compounds with copper(II)

P. D. Wadhavane, L. Gorla, A. Ferrer, B. Altava, M. I. Burguete, M. Á. Izquierdo and S. V. Luis, RSC Adv., 2015, 5, 72579 DOI: 10.1039/C5RA15852D

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