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Org Biomol Chem ; 14(48): 11371-11380, 2016 Dec 07.
Artigo em Inglês | MEDLINE | ID: mdl-27805236

RESUMO

We describe the qualitative and quantitative analysis of the complexation properties towards cations of a cyclic peptoid hexamer composed of alternating α- and ß-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+).


Assuntos
Peptoides/química , Cátions Bivalentes/química , Dicroísmo Circular , Fluorescência , Modelos Moleculares , Estrutura Molecular , Espectroscopia de Prótons por Ressonância Magnética
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