Mechanistic Investigation of the Oxidation of Lysine by Oxone

Sundar, M.; Easwaramoorthy, D.; Rani, S. Kutti; Palanichamy, M.

doi:10.1007/s10953-007-9169-7

Cited by 8 publications

(7 citation statements)

References 13 publications

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“…This observation suggested that the reaction was catalyzed by acetate ion and the positive intercept obtained revealed that the oxidation of vanillin by PMS involved two steps, one catalysed by acetate ion and the other independent of acetate ion. Similar behaviour has been observed in the oxidation of Lysine by peroxomonosulphate [14].…”

Section: Effect Of [Sodium Acetate] On K Obssupporting

confidence: 80%

Oxidation of vanillin by peroxomonosulphate-thermodynamic and kinetic investigation

Rani

Kumar

Wilson

et al. 2009

Journal of Industrial and Engineering Chemistry

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Section: Effect Of [Sodium Acetate] On K Obssupporting

confidence: 80%

Oxidation of vanillin by peroxomonosulphate-thermodynamic and kinetic investigation

Rani

Kumar

Wilson

et al. 2009

Journal of Industrial and Engineering Chemistry

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“…The transformation of several aliphatic amino acids by PMS has been reported at elevated temperatures (30–45 °C) and low pH values (≤5.2): glycine, alanine, leucine, valine, serine, and threonine. These studies reported rate constants determined by following the concentration of PMS and not the amino acid; the products of reaction were determined by a spot test and found to be aldehydes in all cases. − Oxidation of methionine (Met)- and tryptophan (Trp)-containing peptides by PMS has also been studied, but rate constants were not determined . In the case of methionine, the oxidation product was found to be methionine sulfone; transformation products of Trp were not reported .…”

Section: Introductionmentioning

confidence: 99%

Peroxymonosulfate Oxidizes Amino Acids in Water without Activation

Ruiz

Yang

Lochbaum

et al. 2019

Environ. Sci. Technol.

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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 (E H 0 = 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 aqueous components of an organic Oxone reaction are oxidizing and acidic and should be quenched with sodium bisulfite and then neutralized with sodium bicarbonate, resulting in the formation of a mixture of nonhazardous sulfate salts in water. 12 It was apparent that Oxone could potentially oxidize borneol to camphor in the presence of sodium bromide based on work by Koo and co-workers. 13 Because borneol is oxidized easily relative to other aliphatic secondary alcohols, this system was explored ABSTRACT: A new green oxidation procedure was developed for the undergraduate organic teaching laboratories using Oxone and a catalytic quantity of sodium chloride for the conversion of borneol to camphor.…”

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confidence: 99%

Oxidation of Borneol to Camphor Using Oxone and Catalytic Sodium Chloride: A Green Experiment for the Undergraduate Organic Chemistry Laboratory

2011

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ACKNOWLEDGMENTWe thank the students and teaching assistants in the 2311 Organic Chemistry Laboratory course spring and summer semesters of 2010 for their participation in the development of this new laboratory experiment. We also thank Letitia J. Yao for her assistance with the 1 H NMR data and Patrick Schildt and the organic chemistry stockroom personnel for their patience and support in trial runs of a new experiment.

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Mechanistic Investigation of the Oxidation of Lysine by Oxone

Cited by 8 publications

References 13 publications

Oxidation of vanillin by peroxomonosulphate-thermodynamic and kinetic investigation

Oxidation of vanillin by peroxomonosulphate-thermodynamic and kinetic investigation

Peroxymonosulfate Oxidizes Amino Acids in Water without Activation

Oxidation of Borneol to Camphor Using Oxone and Catalytic Sodium Chloride: A Green Experiment for the Undergraduate Organic Chemistry Laboratory

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