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The pivotal role of copper(II) in the enantiorecognition of tryptophan and histidine by gold nanoparticles

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Abstract

Stereoselective amino acid analysis has increasingly moved into the scope of interest of the scientific community. In this work, we report a study on the chiral recognition of d,l-Trp and d,l-His using l-Cys-capped gold nanoparticles (AuNPs) and copper(II) ion. In the l-Cys-capped AuNPs, the thiol group of the amino acid interacts with AuNPs through the formation of Au–S bond, whereas the α-amino and α-carboxyl groups of the surface-confined cysteine 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 spectra and dynamic light scattering measurements, obtaining different results for l- and d-Trp, as well as for l- and d-His. The knowledge of the solution equilibria of the investigated systems allowed us to accurately calculate in advance the concentrations of the species present in solution and to optimize the system performances, highlighting the pivotal role of copper(II) ion in the enantiodiscrimination processes.

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Acknowledgements

We thank Valeria Zito (Istituto CNR di Biostrutture e Bioimmagini, Catania, Italy) for technical assistance and thank Università di Catania (Progetti di Ricerca di Ateneo) for financial support.

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Authors and Affiliations

  1. Dipartimento di Scienze Chimiche, Università degli Studi di Catania, Viale A. Doria 6, 95125, Catania, Italy

    Annalinda Contino & Giuseppe Maccarrone

  2. Dipartimento di Fisica e Astronomia, Università degli Studi di Catania, Via S. Sofia 64, 95123, Catania, Italy

    Massimo Zimbone, Paolo Musumeci & Lucia Calcagno

  3. Istituto di Biostruttura e Bioimmagini, CNR, Viale Andrea Doria 6, 95125, Catania, Italy

    Alessandro Giuffrida

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  1. Annalinda Contino
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  2. Giuseppe Maccarrone
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  3. Massimo Zimbone
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  4. Paolo Musumeci
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  5. Alessandro Giuffrida
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  6. Lucia Calcagno
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Correspondence to Annalinda Contino.

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Contino, A., Maccarrone, G., Zimbone, M. et al. The pivotal role of copper(II) in the enantiorecognition of tryptophan and histidine by gold nanoparticles. Anal Bioanal Chem 406, 481–491 (2014). https://doi.org/10.1007/s00216-013-7466-0

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