title: Synthesis and complexing properties of cyclic benzylopeptoids - a new family of extended macrocyclic peptoids.
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.
authors.affiliation: Department of Chemistry and Biology "A. Zambelli", University of Salerno, Via Giovanni Paolo II, 132, I-84084, Fisciano, Salerno, Italy. dericca@unisa.it.
authors.forename: A
authors.initials: A
authors.lastname: Meli
authors.affiliation: Department of Chemistry and Biology "A. Zambelli", University of Salerno, Via Giovanni Paolo II, 132, I-84084, Fisciano, Salerno, Italy. dericca@unisa.it.
authors.forename: S
authors.initials: S
authors.lastname: Gambaro
authors.affiliation: Department of Chemistry and Biology "A. Zambelli", University of Salerno, Via Giovanni Paolo II, 132, I-84084, Fisciano, Salerno, Italy. dericca@unisa.it.
authors.forename: C
authors.initials: C
authors.lastname: Costabile
authors.affiliation: Department of Chemistry and Biology "A. Zambelli", University of Salerno, Via Giovanni Paolo II, 132, I-84084, Fisciano, Salerno, Italy. dericca@unisa.it.
authors.forename: C
authors.initials: C
authors.lastname: Talotta
authors.affiliation: Department of Chemistry and Biology "A. Zambelli", University of Salerno, Via Giovanni Paolo II, 132, I-84084, Fisciano, Salerno, Italy. dericca@unisa.it.
authors.forename: G
authors.initials: G
authors.lastname: Della Sala
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Trieste, Via L. Giorgieri, I-34127 Trieste, Italy.
authors.forename: P
authors.initials: P
authors.lastname: Tecilla
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Trieste, Via L. Giorgieri, I-34127 Trieste, Italy.
authors.forename: D
authors.initials: D
authors.lastname: Milano
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Trieste, Via L. Giorgieri, I-34127 Trieste, Italy.
authors.forename: M
authors.initials: M
authors.lastname: Tosolini
authors.affiliation: Department of Chemistry and Biology "A. Zambelli", University of Salerno, Via Giovanni Paolo II, 132, I-84084, Fisciano, Salerno, Italy. dericca@unisa.it.
authors.forename: I
authors.initials: I
authors.lastname: Izzo
authors.affiliation: Department of Chemistry and Biology "A. Zambelli", University of Salerno, Via Giovanni Paolo II, 132, I-84084, Fisciano, Salerno, Italy. dericca@unisa.it.
authors.forename: F
authors.initials: F
authors.lastname: De Riccardis
mesh_terms: D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D017136:Ion Transport; D007476:Ionophores / Q000138:chemical synthesis* / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D034444:Peptoids / Q000138:chemical synthesis* / Q000737:chemistry; D012964:Sodium / Q000737:chemistry
chemical_list: D001593:Benzyl Compounds; D007476:Ionophores; D047028:Macrocyclic Compounds; D034444:Peptoids; D012964:Sodium