Stereoselective amino acid analysis is still a challenging task. In this work, we report a study on the chiral recognition of D,L-Trp and D,L-His using L-Cys capped silver nanoparticles (AgNPs) and copper(II) ion. The AgNPs have been characterized by TEM, UV-Vis spectra and dynamic light scattering (DLS) measurements and used for chiral discrimination. In the L-Cys capped AgNPs, the alpha-amino and alpha-carboxyl groups of the surface-confined amino acid, besides showing either a negative or a neutral charge as a function of the pH, can coordinate the copper(II) ion, which in turn, binds the L- or D-amino acid present in solution forming diastereoisomeric complexes. The resulting systems have been characterized by UV-Vis spectroscopy, exploiting the zwitterionic nature of the cysteine to obtain enantiodiscrimination by a fine tuning of the pH. The analysis of the UV-Vis data by using a multiwavelength approach allows us to determine the kinetic constants ruling the processes

Fine tuning the pH triggers the enantiorecognition of underivatized amino acids by silver nanoparticles: A novel approach based on the focused use of solution equilibria

CONTINO, Annalinda;MACCARRONE, Giuseppe;ZIMBONE, MASSIMO;MUSUMECI, Paolo;CALCAGNO, Lucia;
2015

Abstract

Stereoselective amino acid analysis is still a challenging task. In this work, we report a study on the chiral recognition of D,L-Trp and D,L-His using L-Cys capped silver nanoparticles (AgNPs) and copper(II) ion. The AgNPs have been characterized by TEM, UV-Vis spectra and dynamic light scattering (DLS) measurements and used for chiral discrimination. In the L-Cys capped AgNPs, the alpha-amino and alpha-carboxyl groups of the surface-confined amino acid, besides showing either a negative or a neutral charge as a function of the pH, can coordinate the copper(II) ion, which in turn, binds the L- or D-amino acid present in solution forming diastereoisomeric complexes. The resulting systems have been characterized by UV-Vis spectroscopy, exploiting the zwitterionic nature of the cysteine to obtain enantiodiscrimination by a fine tuning of the pH. The analysis of the UV-Vis data by using a multiwavelength approach allows us to determine the kinetic constants ruling the processes
File in questo prodotto:
Non ci sono file associati a questo prodotto.

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/20.500.11769/18648
Citazioni
  • ???jsp.display-item.citation.pmc??? 0
  • Scopus 9
  • ???jsp.display-item.citation.isi??? 10
social impact