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

TECILLA, PAOLO;TOSOLINI, MASSIMO;
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.
http://pubs.rsc.org/en/Content/ArticleLanding/2016/OB/C6OB01683A#!divAbstract
File in questo prodotto:
File Dimensione Formato  
2016_OBC_newcycles.pdf

non disponibili

Descrizione: Articolo principale
Tipologia: Documento in Versione Editoriale
Licenza: Digital Rights Management non definito
Dimensione 897.19 kB
Formato Adobe PDF
897.19 kB Adobe PDF   Visualizza/Apri   Richiedi una copia
c6ob01683a1.pdf

non disponibili

Descrizione: Supporting information
Tipologia: Altro materiale allegato
Licenza: Digital Rights Management non definito
Dimensione 7.36 MB
Formato Adobe PDF
7.36 MB Adobe PDF   Visualizza/Apri   Richiedi una copia
2891605_2016_OBC_newcycles-PostPrint.pdf

accesso aperto

Descrizione: Post Print VQR3
Tipologia: Bozza finale post-referaggio (post-print)
Licenza: Digital Rights Management non definito
Dimensione 1.41 MB
Formato Adobe PDF
1.41 MB Adobe PDF Visualizza/Apri
2891605_c6ob01683a1-PostPrint.pdf

accesso aperto

Descrizione: Post Print VQR3
Tipologia: Bozza finale post-referaggio (post-print)
Licenza: Digital Rights Management non definito
Dimensione 7.7 MB
Formato Adobe PDF
7.7 MB 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: http://hdl.handle.net/11368/2891605
Citazioni
  • ???jsp.display-item.citation.pmc??? 3
  • Scopus 17
  • ???jsp.display-item.citation.isi??? 18
social impact