Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 14, Issue 38, Pages 9055-9062Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ob01683a
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Funding
- University of Salerno (FARB)
- Italian Ministero dell'Universita e della Ricerca (MIUR) [PRIN 20109Z2XRJ_006]
- Regione Campania under POR Campania FESR [O.O. 2.1]
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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.
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