A practical synthesis of preorganized tripodal enterobactin/corynebactin-type ligands (consisting of a C3-symmetric macrocyclic peptoid core, three catecholamide coordinating units, and C2, C4, and C6 spacers) is reported. The formation of complexes with Fe3+ was investigated by spectrophotometric (UV-Vis) and spectrometric (ESI, negative ionization mode) methods and corroborated by theoretical (DFT) calculations. Preliminary studies revealed the intricate interplay between the conformational chirality of cyclic trimeric peptoids and metal coordination geometry of mononuclear species similar to that of natural catechol-based siderophores. Experimental results demonstrated the unexpected formation of unique dinuclear Fe3+ complexes.

Peptoid-based siderophore mimics as dinuclear Fe3+ chelators

D'Amato, Assunta
Membro del Collaboration Group
;
Costabile, Chiara
Membro del Collaboration Group
;
Della Sala, Giorgio
Membro del Collaboration Group
;
Izzo, Irene
Membro del Collaboration Group
;
Maayan, Galia
Membro del Collaboration Group
;
De Riccardis, Francesco
2020

Abstract

A practical synthesis of preorganized tripodal enterobactin/corynebactin-type ligands (consisting of a C3-symmetric macrocyclic peptoid core, three catecholamide coordinating units, and C2, C4, and C6 spacers) is reported. The formation of complexes with Fe3+ was investigated by spectrophotometric (UV-Vis) and spectrometric (ESI, negative ionization mode) methods and corroborated by theoretical (DFT) calculations. Preliminary studies revealed the intricate interplay between the conformational chirality of cyclic trimeric peptoids and metal coordination geometry of mononuclear species similar to that of natural catechol-based siderophores. Experimental results demonstrated the unexpected formation of unique dinuclear Fe3+ complexes.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11386/4744548
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