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.

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

MELI, ALESSANDRA;GAMBARO, STEFANIA;COSTABILE, Chiara;TALOTTA, CARMEN;DELLA SALA, Giorgio;IZZO, Irene;DE RICCARDIS, Francesco
2016

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.
File in questo prodotto:
File Dimensione Formato  
De Riccardis for on line submission_watermark-2_watermark.pdf

accesso aperto

Tipologia: Documento in Pre-print (manoscritto inviato all'editore, precedente alla peer review)
Licenza: Creative commons
Dimensione 728.93 kB
Formato Adobe PDF
728.93 kB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11386/4676658
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? 3
  • Scopus 18
  • ???jsp.display-item.citation.isi??? 19
social impact