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Selective complexation of divalent cations by a cyclic α,β-peptoid hexamer: a spectroscopic and computational study

Selective complexation of divalent cations by a cyclic α,β-peptoid hexamer: a spectroscopic and computational study

De Santis, E., Edwards, A. A., Alexander, Bruce, Holder, S. J., Biesse-Martin, A.-S., Nielsen, B. V., Mistry, D., Waters, L., Siligardi, G., Hussain, R., Faure, S. and Taillefumier, C. (2016) Selective complexation of divalent cations by a cyclic α,β-peptoid hexamer: a spectroscopic and computational study. Organic and Biomolecular Chemistry, 14 (48). pp. 11371-11380. ISSN 1477-0520 (Print), 1477-0539 (Online) (doi:10.1039/C6OB01954D)

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Abstract

We describe the qualitative and quantitative analysis of the complexation properties towards cations of a cyclic peptoid hexamer composed of alternating α- and β-peptoid monomers, which bear exclusively chiral (S)-phenylethyl side chains (spe) that have no noticeable chelating properties. The binding of a series of monovalent and divalent cations was assessed by 1H NMR, circular dichroism, fluorescence and molecular modelling. In contrast to previous studies on cations binding by 18-membered α-cyclopeptoid hexamers, the 21-membered cyclopeptoid cP1 did not complex monovalent cations (Na+, K+, Ag+) but showed selectivity for divalent cations (Ca2+, Ba2+, Sr2+ and Mg2+). Hexacoordinated C-3 symmetrical complexes were demonstrated for divalent cations with ionic radii around 1 Å (Ca2+ and Ba2+), while 5-coordination is preferred for divalent cations with larger (Ba2+) or smaller ionic radii (Mg2+).

Item Type: Article
Additional Information: This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Uncontrolled Keywords: Circular dichroism; Peptoids; Spectroscopy; Binding
Subjects: Q Science > QD Chemistry
Faculty / Department / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > Department of Pharmaceutical, Chemical & Environmental Sciences
Last Modified: 31 Aug 2017 09:57
Selected for GREAT 2016: None
Selected for GREAT 2017: GREAT a
Selected for GREAT 2018: None
URI: http://gala.gre.ac.uk/id/eprint/16492

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