Peroxymonosulfate Oxidizes Amino Acids in Water without Activation

  • Mercedes Ruiz
    Mercedes Ruiz
    Environmental Chemistry and Technology Program, University of Wisconsin, Madison, Wisconsin 53706, United States
  • Yi Yang
    Yi Yang
    Department of Environmental Sciences, The Connecticut Agricultural Experiment Station, New Haven, Connecticut 06511, United States
    More by Yi Yang
  • Christian A. Lochbaum
    Christian A. Lochbaum
    Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, United States
  • Daniel G. Delafield
    Daniel G. Delafield
    Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, United States
  • Joseph J. Pignatello
    Joseph J. Pignatello
    Department of Environmental Sciences, The Connecticut Agricultural Experiment Station, New Haven, Connecticut 06511, United States
  • Lingjun Li
    Lingjun Li
    Department of Chemistry,  School of Pharmacy, University of Wisconsin, Madison, Wisconsin 53706, United States
    More by Lingjun Li
  • , and 
  • Joel A. Pedersen*
    Joel A. Pedersen
    Environmental Chemistry and Technology Program,  Department of Chemistry,  Departments of Soil Science and Civil & Environmental Engineering, University of Wisconsin, Madison, Wisconsin 53706, United States
    *E-mail: [email protected]. Phone: +1 (608) 263-4971.
Cite this: Environ. Sci. Technol. 2019, 53, 18, 10845–10854
Publication Date (Web):August 2, 2019
https://doi.org/10.1021/acs.est.9b01322
Copyright © 2019 American Chemical Society
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Abstract

A variety of peptidic and proteinaceous contaminants (e.g., proteins, toxins, pathogens) present in the environment may pose risk to human health and wildlife. Peroxymonosulfate is a strong oxidant (EH0 = 1.82 V for HSO5, the predominant species at environmental pH values) that may hold promise for the deactivation of proteinaceous contaminants. Relatively little quantitative information exists on the rates of peroxymonosulfate reactions with free amino acids. Here, we studied the oxidation of 19 of the 20 standard proteinogenic amino acids (all except cysteine) by peroxymonosulfate without explicit activation. Reaction half-lives at pH 7 ranged from milliseconds to hours. Amino acids possessing sulfur-containing, heteroaromatic, or substituted aromatic side chains were the most susceptible to oxidation by peroxymonosulfate, with rates of transformation decreasing in the order methionine > tryptophan > tyrosine > histidine. The rate of tryptophan oxidation did not decrease in the presence of an aquatic natural organic matter. Singlet oxygen resulting from peroxymonosulfate self-decomposition, while detected by electron paramagnetic resonance spectroscopy, was unlikely to be the principal reactive species. Our results demonstrate that peroxymonosulfate is capable of oxidizing 19 amino acids without explicit activation and that solvent-exposed methionine and tryptophan residues are likely initial targets of oxidation in peptides and proteins.

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.est.9b01322.

  • Additional experimental procedures, instrumental parameters, and data analyses; peroxymonosulfate and amino acid stability, pseudo-first-order rate constants, and mass spectral data for transformation products (PDF)

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