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

DOI: 10.1039/C6OB01954D DOI Help

Authors: E. De Santis (Medway School of Pharmacy) , A. A. Edwards (Medway School of Pharmacy) , B. D. Alexander (University of Greenwich) , S. J. Holder (Functional Materials Group, School of Physical Sciences, University of Kent) , A.-s. Biesse-martin (Université Clermont Auvergne, Université Blaise Pascal, Institut de Chimie de Clermont-Ferrand; CNRS) , B. V. Nielsen (University of Greenwich) , D. Mistry (Division of Pharmacy and Pharmaceutical Sciences, University of Huddersfield) , L. Waters (Division of Pharmacy and Pharmaceutical Sciences, University of Huddersfield) , G. Siligardi (Diamond Light Source) , R. Hussain (Diamond Light Source) , S. Faure (Université Clermont Auvergne, Université Blaise Pascal, Institut de Chimie de Clermont-Ferrand; CNRS) , C. Taillefumier (Université Clermont Auvergne, Université Blaise Pascal, Institut de Chimie de Clermont-Ferrand; CNRS)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Org. Biomol. Chem.

State: Published (Approved)
Published: November 2016
Diamond Proposal Number(s): 7104 , 6657

Open Access Open Access

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+).

Subject Areas: Biology and Bio-materials


Instruments: B23-Circular Dichroism

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