Peroxides. II. Preparation, Characterization and Polarographic Behavior of Longchain Aliphatic Peracids<sup>2</sup>

Parker, W.; Ricciuti, Constantine; Ogg, C L; Swern, Daniel

doi:10.1021/ja01620a023

Cited by 110 publications

(34 citation statements)

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“…Peroxytertradecanoic acid was chemically synthesized, using Parker’s method [9] in the reaction of tetradecanoic acid with hydrogen peroxide (from Sigma). The purity of the prepared compound was tested with NMR and IR spectroscopy.…”

Section: Methodsmentioning

confidence: 99%

“…Due to the fact that peroxy acids are strong oxidants and may inactivate the PTPs via oxidation of catalytic center thiolate, we decided to investigate whether peroxytetradecanoic acid would have an effect on phosphatase CD45 activity [9]. We have investigated and compared the effects of treatment with hydrogen peroxide and peroxytetradecanoic acid on the enzymatic activity of recombinant CD45.…”

Section: Introductionmentioning

confidence: 99%

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Activation of Hydrogen Peroxide to Peroxytetradecanoic Acid Is Responsible for Potent Inhibition of Protein Tyrosine Phosphatase CD45

et al. 2012

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Hydrogen peroxide induces oxidation and consequently inactivation of many protein tyrosine phosphatases. It was found that hydrogen peroxide, in the presence of carboxylic acids, was efficiently activated to form even more potent oxidant - peroxy acid. We have found that peroxytetradecanoic acid decreases the enzymatic activity of CD45 phosphatase significantly more than hydrogen peroxide. Our molecular docking computational analysis suggests that peroxytetradecanoic acid has a higher binding affinity to the catalytic center of CD45 than hydrogen peroxide.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Activation of Hydrogen Peroxide to Peroxytetradecanoic Acid Is Responsible for Potent Inhibition of Protein Tyrosine Phosphatase CD45

et al. 2012

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“…Peracids were synthesized according Parker's method [25] as a result of the reaction of a carboxylic acid of interest, and hydrogen peroxide. The carboxylic acid of interest was added into the solution of 50-60% hydrogen peroxide and 70% sulfuric acid (as a reaction medium), and the reaction mixture was incubated for 2 hours at a room temperature, and then purified.…”

Section: Peracid Synthesismentioning

confidence: 99%

Inactivation of Protein Tyrosine Phosphatases by Peracids Correlates with the Hydrocarbon Chain Length

Kuban–Jankowska

Górska

Tuszyński

et al. 2015

Cell Physiol Biochem

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Background/Aims: Protein tyrosine phosphatases are crucial enzymes controlling numerous physiological and pathophysiological events and can be regulated by oxidation of the catalytic domain cysteine residue. Peracids are highly oxidizing compounds, and thus may induce inactivation of PTPs. The aim of the present study was to evaluate the inhibitory effect of peracids with different length of hydrocarbon chain on the activity of selected PTPs. Methods: The enzymatic activity of human CD45, PTP1B, LAR, bacterial YopH was assayed under the cell-free conditions, and activity of cellular CD45 in human Jurkat cell lysates. The molecular docking and molecular dynamics were performed to evaluate the peracids binding to the CD45 active site. Results: Here we demonstrate that peracids reduce enzymatic activity of recombinant CD45, PTP1B, LAR, YopH and cellular CD45. Our studies indicate that peracids are more potent inhibitors of CD45 than hydrogen peroxide (with an IC50 value equal to 25 nM for peroctanoic acid and 8 µM for hydrogen peroxide). The experimental data show that the inactivation caused by peracids is dependent on hydrocarbon chain length of peracids with maximum inhibitory effect of medium-chain peracids (C8-C12 acyl chain), which correlates with calculated binding affinities to the CD45 active site. Conclusion: Peracids are potent inhibitors of PTPs with the strongest inhibitory effect observed for medium-chain peracids.

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“…In the condensed phase, however, the formation of peracids from the carboxylic acid is reversible, with presence of liquid water shifting the equilibrium towards the acid (d 'Ans and Frey, 1912;Parker et al, 1955). Increased humidity, leading to an increased fraction of water in in the particle phase, could therefore lead to less peroxypinic acid in α-pinene ozonolysis SOA.…”

Section: Humid Vs Dry Conditionsmentioning

confidence: 99%

Synthesis and characterization of peroxypinic acids as proxies for highly oxygenated molecules (HOMs) in secondary organic aerosol

Steimer¹,

Delvaux²,

Campbell³

et al. 2018

Preprint

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Abstract. Peroxy acids might contribute significantly to particle toxicity and were recently found to be involved in new particle formation in the atmosphere. However, a lack of suitable analytical methods for the detection and characterization of peroxy acids in the particle phase is currently hindering the quantitative investigation of their contribution to these important 10 atmospheric processes. Further development of appropriate techniques and relevant standards is therefore urgently needed.In this study, we synthesized three peroxypinic acids, developed a liquid chromatography separation method and characterised them with tandem mass spectrometry. The observed fragmentation patterns clearly distinguish the different peroxypinic acids from both the acid and each other, showing several neutral losses previously already observed for other peroxy acids. Both monoperoxypinic acids were found to be present in secondary organic aerosol generated from ozonolysis 15 of α-pinene in laboratory experiments. The yield of monoperoxypinic acid formation was not influenced by humidity.Monoperoxypinic acid quickly degrades on the filter, with about 60% lost within the first 5 hours. This fast degradation shows that time delays in traditional off-line analysis will likely lead to severe underestimates of peroxy compound concentrations in ambient particles.

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Peroxides. II. Preparation, Characterization and Polarographic Behavior of Longchain Aliphatic Peracids²

Cited by 110 publications

References 0 publications

Activation of Hydrogen Peroxide to Peroxytetradecanoic Acid Is Responsible for Potent Inhibition of Protein Tyrosine Phosphatase CD45

Activation of Hydrogen Peroxide to Peroxytetradecanoic Acid Is Responsible for Potent Inhibition of Protein Tyrosine Phosphatase CD45

Inactivation of Protein Tyrosine Phosphatases by Peracids Correlates with the Hydrocarbon Chain Length

Synthesis and characterization of peroxypinic acids as proxies for highly oxygenated molecules (HOMs) in secondary organic aerosol

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Peroxides. II. Preparation, Characterization and Polarographic Behavior of Longchain Aliphatic Peracids2

Cited by 110 publications

References 0 publications

Activation of Hydrogen Peroxide to Peroxytetradecanoic Acid Is Responsible for Potent Inhibition of Protein Tyrosine Phosphatase CD45

Activation of Hydrogen Peroxide to Peroxytetradecanoic Acid Is Responsible for Potent Inhibition of Protein Tyrosine Phosphatase CD45

Inactivation of Protein Tyrosine Phosphatases by Peracids Correlates with the Hydrocarbon Chain Length

Synthesis and characterization of peroxypinic acids as proxies for highly oxygenated molecules (HOMs) in secondary organic aerosol

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Peroxides. II. Preparation, Characterization and Polarographic Behavior of Longchain Aliphatic Peracids²