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

E. De Santis, Alison A. Edwards, Bruce David Alexander, S. J. Holder, A.-S. Biesse-Martin, B. V. Nielsen, Dharmit Mistry, L. Waters, G. Siligardi, Rabia Hussain, S. Faure, C. Taillefumier

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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+).
Original languageEnglish
Pages (from-to)11371-11380
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number48
Early online date2 Nov 2016
DOIs
Publication statusPublished - 2016

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    De Santis, E., Edwards, A. A., Alexander, B. D., Holder, S. J., Biesse-Martin, A-S., Nielsen, B. V., Mistry, D., Waters, L., Siligardi, G., Hussain, R., Faure, S., & 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), 11371-11380. https://doi.org/10.1039/C6OB01954D