Electrochemically initiated 1,4 additions: a versatile route to the determination of thiols

PC White, NS Lawrence, J Davis, RG Compton

    Research output: Contribution to journal › Article

    111 Citations (Scopus)

    Abstract

    The electrochemical generation of quinoid intermediates and their subsequent reaction with sulphydryl thiols (RSH) have been investigated as a method by which the latter can be quantified. Nucleophilic addition of the thiol species to the electrogenerated quinoid structure leads to the production of a chemically reduced adduct whose subsequent re-oxidation at the electrode leads to an amplification of the oxidative current. This can be correlated to the concentration of thiol present within the medium. The influence of indicator composition on the nature of the analytical response has been assessed through examining the electrochemical properties of 15 derivatives and the validity of the proposed reaction pathway corroborated by comparison of the voltammetric response with computer simulations. Interference by other electroactive species (ascorbate, urate, tyrosine) and other physiological constituents (cystine, lysine) has also been assessed. (C) 2001 Elsevier Science B.V. All rights reserved.
    LanguageEnglish
    Pages1-10
    JournalAnalytica Chimica Acta
    Volume447
    Issue number1-2
    Publication statusPublished - Nov 2001

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    Sulfhydryl Compounds
    Cystine
    Uric Acid
    Electrochemical properties
    Lysine
    Amplification
    Tyrosine
    Derivatives
    Oxidation
    Electrodes
    Computer simulation
    Chemical analysis

    Cite this

    White, PC ; Lawrence, NS ; Davis, J ; Compton, RG. / Electrochemically initiated 1,4 additions: a versatile route to the determination of thiols. In: Analytica Chimica Acta. 2001 ; Vol. 447, No. 1-2. pp. 1-10.
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    abstract = "The electrochemical generation of quinoid intermediates and their subsequent reaction with sulphydryl thiols (RSH) have been investigated as a method by which the latter can be quantified. Nucleophilic addition of the thiol species to the electrogenerated quinoid structure leads to the production of a chemically reduced adduct whose subsequent re-oxidation at the electrode leads to an amplification of the oxidative current. This can be correlated to the concentration of thiol present within the medium. The influence of indicator composition on the nature of the analytical response has been assessed through examining the electrochemical properties of 15 derivatives and the validity of the proposed reaction pathway corroborated by comparison of the voltammetric response with computer simulations. Interference by other electroactive species (ascorbate, urate, tyrosine) and other physiological constituents (cystine, lysine) has also been assessed. (C) 2001 Elsevier Science B.V. All rights reserved.",
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    White, PC, Lawrence, NS, Davis, J & Compton, RG 2001, 'Electrochemically initiated 1,4 additions: a versatile route to the determination of thiols', Analytica Chimica Acta, vol. 447, no. 1-2, pp. 1-10.

    Electrochemically initiated 1,4 additions: a versatile route to the determination of thiols. / White, PC; Lawrence, NS; Davis, J; Compton, RG.

    In: Analytica Chimica Acta, Vol. 447, No. 1-2, 11.2001, p. 1-10.

    Research output: Contribution to journal › Article

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    AB - The electrochemical generation of quinoid intermediates and their subsequent reaction with sulphydryl thiols (RSH) have been investigated as a method by which the latter can be quantified. Nucleophilic addition of the thiol species to the electrogenerated quinoid structure leads to the production of a chemically reduced adduct whose subsequent re-oxidation at the electrode leads to an amplification of the oxidative current. This can be correlated to the concentration of thiol present within the medium. The influence of indicator composition on the nature of the analytical response has been assessed through examining the electrochemical properties of 15 derivatives and the validity of the proposed reaction pathway corroborated by comparison of the voltammetric response with computer simulations. Interference by other electroactive species (ascorbate, urate, tyrosine) and other physiological constituents (cystine, lysine) has also been assessed. (C) 2001 Elsevier Science B.V. All rights reserved.

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    White PC, Lawrence NS, Davis J, Compton RG. Electrochemically initiated 1,4 additions: a versatile route to the determination of thiols. Analytica Chimica Acta. 2001 Nov;447(1-2):1-10.