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Elemental labelling and mass spectrometry for the specific detection of sulfenic acid groups in model peptides: a proof of concept

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Abstract

Oxidative transformation of cysteine thiol groups into different functional groups is considered a significant posttranslational modification of great importance in pathological and physiological processes. A cysteine sulfenic acid (SA) residue is the transient state for thiol group oxidation and it can react with free thiols to form disulfide bonds or can be further oxidized with reactive oxygen/reactive nitrogen species (ROS/RNS) to form sulfinic and sulfonic acids. The increase in ROS/RNS concentrations is correlated to age-related diseases such as cancer and Alzheimer’s disease. Since the formation of SA represents a transient state of oxidation of thiols, its formation can be considered a redox-sensitive sensor for the presence of ROS/RNS. Thereby, the detection of the short-lived SA will provide greater insight into the redox-mediated events that alter the structure and function of peptides and proteins. The aim of this study is to provide a new strategy for the highly sensitive and specific detection of SA in peptides as a proof of concept. For this aim, SA was firstly generated in model peptides on oxidation with H2O2 and then captured by the linear alkyne β-ketoester (KE) previously linked to a lanthanide (Ln)-containing chelator (Ln-DOTA, where DOTA is 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid). The linking of the KE to DOTA was performed by click chemistry, resulting in a new reagent (Ln-DOTA-KE) that permits highly sensitive elemental (inductively coupled plasma) and molecular (electrospray) mass spectrometric detection. The new reagent (Ln-DOTA-KE) reacts specifically with SA, offering improved reactivity at physiological pH, facile derivatization and a cell-membrane-permeable compound that has promising future applications.

A new derivatizing reagent for specific detection of sulphenic acid (SA) generated in model peptides by oxidation of cysteine groups is presented in this work.

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Acknowledgements

This work was financially supported by the Deutsche Forschungsgemeinschaft (German Research Foundation). M.S. acknowledges the graduate program of the School of Analytical Sciences in Adlershof (SALSA) for funding through scholarship.

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Authors and Affiliations

  1. Department of Chemistry, Humboldt University of Berlin, Brook-Taylor-Str. 2, 12489, Berlin, Germany

    Mona Sharar, Christoph Arenz & Michael W. Linscheid

  2. Institute for Chemistry, Humboldt Universität zu Berlin, 12489, Berlin, Germany

    Essa M. Saied

  3. Chemistry Department, Faculty of Science, Suez Canal University, 41522, Ismailia, Egypt

    Essa M. Saied

  4. Department of Physical and Analytical Chemistry, University of Oviedo, C/Julian Claveria 8, 33006, Oviedo, Spain

    Mario C. Rodriguez & Maria Montes-Bayón

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  1. Mona Sharar
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  2. Essa M. Saied
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  3. Mario C. Rodriguez
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  4. Christoph Arenz
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  5. Maria Montes-Bayón
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  6. Michael W. Linscheid
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Correspondence to Maria Montes-Bayón or Michael W. Linscheid.

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Sharar, M., Saied, E.M., Rodriguez, M.C. et al. Elemental labelling and mass spectrometry for the specific detection of sulfenic acid groups in model peptides: a proof of concept. Anal Bioanal Chem 409, 2015–2027 (2017). https://doi.org/10.1007/s00216-016-0149-x

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  • DOI: https://doi.org/10.1007/s00216-016-0149-x

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