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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

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Biolabeling with cobaltocinium tags

Susanne Müller-Bomke
  • Westfälische Wilhelms-Universität Münster, Institute of Inorganic and Analytical Chemistry, Corrensstraße 30, 48149 Münster, Germany
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/ Michael Sperling
  • Westfälische Wilhelms-Universität Münster, Institute of Inorganic and Analytical Chemistry, Corrensstraße 30, 48149 Münster, Germany
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/ Heiko Hayen
  • Westfälische Wilhelms-Universität Münster, Institute of Inorganic and Analytical Chemistry, Corrensstraße 30, 48149 Münster, Germany
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/ Uwe Karst
  • Corresponding author
  • Westfälische Wilhelms-Universität Münster, Institute of Inorganic and Analytical Chemistry, Corrensstraße 30, 48149 Münster, Germany
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Published Online: 2018-08-15 | DOI: https://doi.org/10.1515/znb-2018-0093

Abstract

A label for amino and thiol functionalities of peptides and proteins based on the activated cobaltocinium hexafluorophosphate succinimide ester (CoS) is presented. Despite the known selectivity of a succinimide ester towards amines, CoS also modifies cysteine residues under the same reaction conditions. The derivatized biomolecules were investigated using liquid chromatography with subsequent electrospray-mass spectrometric detection (LC/ESI-MS). In combination with their remarkable stability under physiological conditions, easy handling and good spectroscopic properties, cobaltocinium ions provide all requirements for a powerful labeling reagent. Furthermore, in direct comparison to the isoelectronic well-established ferrocene reagents, the higher redox potential and the chemical stability of the cobaltocinium moiety add to the benefits as a derivatizing agent for bioanalysis.

Graphical Abstract

Keywords: amines; biolabeling; cobaltocinium; electrospray ionization-mass spectrometry (ESI-MS); thiols

Dedicated to: Professor Bernt Krebs on the occasion of his 80th birthday.

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About the article

aThis author’s part of the work was carried out at Leibniz-Institut für Analytische Wissenschaften – ISAS – e.V., Otto-Hahn-Straße 6b, 44227 Dortmund, Germany


Received: 2018-05-20

Accepted: 2018-07-19

Published Online: 2018-08-15


Citation Information: Zeitschrift für Naturforschung B, 20180093, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2018-0093.

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