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Issue 38, 2016
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Synthesis and complexing properties of cyclic benzylopeptoids – a new family of extended macrocyclic peptoids

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Abstract

An efficient protocol for the solid-phase synthesis of six members of a new class of extended macrocyclic peptoids (based on ortho-, meta- and para-N-(methoxyethyl)aminomethyl phenylacetyl units) is described. Theoretical (DFT) and experimental (NMR) studies on the free and Na+-complexed cyclic trimers (3–5) and tetramers (6–8) demonstrate that annulation of the rigidified peptoids can generate new hosts with the ability to sequestrate one or two sodium cations with the affinities and stoichiometries defined by the macrocycle morphology. Ion transport studies have been also performed in order to better appreciate the factors promoting transmembrane cation translocation.

Graphical abstract: Synthesis and complexing properties of cyclic benzylopeptoids – a new family of extended macrocyclic peptoids

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Supplementary files

Article information


Submitted
04 Aug 2016
Accepted
23 Aug 2016
First published
24 Aug 2016

Org. Biomol. Chem., 2016,14, 9055-9062
Article type
Paper

Synthesis and complexing properties of cyclic benzylopeptoids – a new family of extended macrocyclic peptoids

A. Meli, S. Gambaro, C. Costabile, C. Talotta, G. Della Sala, P. Tecilla, D. Milano, M. Tosolini, I. Izzo and F. De Riccardis, Org. Biomol. Chem., 2016, 14, 9055
DOI: 10.1039/C6OB01683A

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