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Issue 48, 2016
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Selective complexation of divalent cations by a cyclic α,β-peptoid hexamer: a spectroscopic and computational study

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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+).

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

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Publication details

The article was received on 05 Sep 2016, accepted on 20 Oct 2016, published on 02 Nov 2016 and first published online on 02 Nov 2016


Article type: Paper
DOI: 10.1039/C6OB01954D
Citation: Org. Biomol. Chem., 2016,14, 11371-11380
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    Selective complexation of divalent cations by a cyclic α,β-peptoid hexamer: a spectroscopic and computational study

    E. De Santis, A. A. Edwards, B. D. Alexander, S. J. Holder, A.-S. Biesse-Martin, B. V. Nielsen, D. Mistry, L. Waters, G. Siligardi, R. Hussain, S. Faure and C. Taillefumier, Org. Biomol. Chem., 2016, 14, 11371
    DOI: 10.1039/C6OB01954D

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