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Molecules 2018, 23(2), 264;

Analysis of Protein-Phenolic Compound Modifications Using Electrochemistry Coupled to Mass Spectrometry

Institute of Food Chemistry, Hamburg School of Food Science, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany
Author to whom correspondence should be addressed.
Received: 13 December 2017 / Revised: 18 January 2018 / Accepted: 24 January 2018 / Published: 29 January 2018
(This article belongs to the Special Issue Protein Modifications and Bioconjugation)
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In the last decade, electrochemical oxidation coupled with mass spectrometry has been successfully used for the analysis of metabolic studies. The application focused in this study was to investigate the redox potential of different phenolic compounds such as the very prominent chlorogenic acid. Further, EC/ESI-MS was used as preparation technique for analyzing adduct formation between electrochemically oxidized phenolic compounds and food proteins, e.g., alpha-lactalbumin or peptides derived from a tryptic digestion. In the first step of this approach, two reactant solutions are combined and mixed: one contains the solution of the digested protein, and the other contains the phenolic compound of interest, which was, prior to the mixing process, electrochemically transformed to several oxidation products using a boron-doped diamond working electrode. As a result, a Michael-type addition led to covalent binding of the activated phenolic compounds to reactive protein/peptide side chains. In a follow-up approach, the reaction mix was further separated chromatographically and finally detected using ESI-HRMS. Compound-specific, electrochemical oxidation of phenolic acids was performed successfully, and various oxidation and reaction products with proteins/peptides were observed. Further optimization of the reaction (conditions) is required, as well as structural elucidation concerning the final adducts, which can be phenolic compound oligomers, but even more interestingly, quite complex mixtures of proteins and oxidation products. View Full-Text
Keywords: adduct formation; protein interaction; electrochemical oxidation; phenolic compounds adduct formation; protein interaction; electrochemical oxidation; phenolic compounds

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Kallinich, C.; Schefer, S.; Rohn, S. Analysis of Protein-Phenolic Compound Modifications Using Electrochemistry Coupled to Mass Spectrometry. Molecules 2018, 23, 264.

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