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“Inherently chiral” thiophene-based electrodes at work: a screening of enantioselection ability toward a series of pharmaceutically relevant phenolic or catecholic amino acids, amino esters, and amine

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An Erratum to this article was published on 27 December 2016

Abstract

“Inherently chiral” thiophene-based electroactive oligomer films have recently been shown to exhibit outstanding chirality manifestations. One of the most exciting among them is an unprecedented enantioselection ability as electrode surfaces. In fact, in preliminary chiral voltammetry experiments, the new electrodes have been shown to both discriminate the enantiomers of chiral probes (either enantiopure or in a mixture, in terms of large differences in peak potentials) and quantify them (in terms of linear dynamic ranges in peak currents), without the need for preliminary separation steps. Such ability has now been tested on a series of chiral DOPA-related molecules, from phenolic amino acid tyrosine (together with its methyl ester) to catecholic amino acid DOPA (together with its methyl ester), to catecholamine epinephrine (adrenaline). The wide-range enantioselectivity of the new inherently chiral electrode surfaces is fully confirmed, as large peak potential differences are obtained for probe enantiomers of the whole series working in common aqueous buffers. Moreover, interesting modulating effects on enantiodiscrimination can be observed as a function of both molecular structure and pH.

Inherently chiral thiophene-based electrodes at work with pharmaceutically relevant probes

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Acknowledgments and funding information

The financial support of Fondazione Cariplo (Materiali avanzati 2011–0417 “Inherently Chiral Multifunctional Conducting Polymers”) is gratefully acknowledged.

The work on inherently chiral materials is also being developed in the context of the SmartMatLab Project at Dipartimento di Chimica, Università degli Studi di Milano, supported by Regione Lombardia (EU FESR and FSE), Fondazione Cariplo, Università degli Studi di Milano, and CNR ISTM.

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Authors and Affiliations

  1. Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133, Milan, Italy

    Serena Arnaboldi, Sara Grecchi, Laura Santagostini, Francesco Sannicolò & Patrizia R. Mussini

  2. Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell’Insubria, Via Valleggio 11, 22100, Como, Italy

    Tiziana Benincori

  3. Dipartimento del Farmaco, Istituto Superiore di Sanità, Viale Regina Elena 299, 00161, Rome, Italy

    Roberto Cirilli

Authors
  1. Serena Arnaboldi
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  2. Tiziana Benincori
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  3. Roberto Cirilli
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  4. Sara Grecchi
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  5. Laura Santagostini
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  6. Francesco Sannicolò
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  7. Patrizia R. Mussini
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Correspondence to Serena Arnaboldi or Patrizia R. Mussini.

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Published in the topical collection Chemical Sensing Systems with guest editors Maria Careri, Marco Giannetto, and Renato Seeber.

An erratum to this article is available at http://dx.doi.org/10.1007/s00216-016-0103-y.

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Arnaboldi, S., Benincori, T., Cirilli, R. et al. “Inherently chiral” thiophene-based electrodes at work: a screening of enantioselection ability toward a series of pharmaceutically relevant phenolic or catecholic amino acids, amino esters, and amine. Anal Bioanal Chem 408, 7243–7254 (2016). https://doi.org/10.1007/s00216-016-9852-x

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