In this work we have investigated the binding properties of a new synthetic receptor for phosphate anions that combines metal ion coordination with electrostatic and H-bonding interactions. The described receptor is obtained by assembling an iminodiacetic (IDA) fragment, as a Zn(II) binding site, with a polyamine macrocyclic portion containing two trans-1,2-diaminocyclohaexane (DAC) units and a pyrrole ring, as a cationic binding site, into an adaptive structure appropriately spanning the length of di- and tridentate phosphates. Potentiometric measurements together with 1H and 31P NMR investigation showed that, in a wide pH range including values of physiological interest, the Zn(II) complex of the receptor binds di- and triphosphates, such as ADP, ATP, pyrophosphate (PP) and triphosphate (TP), far better than monophosphate (MP), and that TP is poorly bound by methyliminodiacetate (MIDA) as a model for the Zn(II) binding site. Besides the excellent selectivity over other phosphates, the affinity for TP is the largest reported to date for Zn(II) complexes in water.

Phosphate binding by a novel Zn(II) complex featuring a trans-​1,​2-​diaminocyclohexane ligand. Effective anion recognition in water / Oscar Francesconi; Matteo Gentili; Francesco Bartoli; Andrea Bencini; Luca Conti; Claudia Giorgi;Stefano Roelens. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - STAMPA. - 13:(2015), pp. 1860-1868. [10.1039/c4ob02321h]

Phosphate binding by a novel Zn(II) complex featuring a trans-​1,​2-​diaminocyclohexane ligand. Effective anion recognition in water

FRANCESCONI, OSCAR;GENTILI, MATTEO;BARTOLI, FRANCESCO;BENCINI, ANDREA
;
CONTI, LUCA;GIORGI, CLAUDIA;ROELENS, STEFANO
2015

Abstract

In this work we have investigated the binding properties of a new synthetic receptor for phosphate anions that combines metal ion coordination with electrostatic and H-bonding interactions. The described receptor is obtained by assembling an iminodiacetic (IDA) fragment, as a Zn(II) binding site, with a polyamine macrocyclic portion containing two trans-1,2-diaminocyclohaexane (DAC) units and a pyrrole ring, as a cationic binding site, into an adaptive structure appropriately spanning the length of di- and tridentate phosphates. Potentiometric measurements together with 1H and 31P NMR investigation showed that, in a wide pH range including values of physiological interest, the Zn(II) complex of the receptor binds di- and triphosphates, such as ADP, ATP, pyrophosphate (PP) and triphosphate (TP), far better than monophosphate (MP), and that TP is poorly bound by methyliminodiacetate (MIDA) as a model for the Zn(II) binding site. Besides the excellent selectivity over other phosphates, the affinity for TP is the largest reported to date for Zn(II) complexes in water.
2015
13
1860
1868
Oscar Francesconi; Matteo Gentili; Francesco Bartoli; Andrea Bencini; Luca Conti; Claudia Giorgi;Stefano Roelens
File in questo prodotto:
File Dimensione Formato  
abstract articolo.pdf

Accesso chiuso

Tipologia: Altro
Licenza: Tutti i diritti riservati
Dimensione 33.89 kB
Formato Adobe PDF
33.89 kB Adobe PDF   Richiedi una copia
OBC 2015.pdf

Accesso chiuso

Descrizione: lavoro pubblicato
Tipologia: Pdf editoriale (Version of record)
Licenza: Tutti i diritti riservati
Dimensione 378.03 kB
Formato Adobe PDF
378.03 kB Adobe PDF   Richiedi una copia

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

Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/969989
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 16
  • ???jsp.display-item.citation.isi??? 14
social impact