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Peroxidase-mediated degradation of perfluorooctanoic acid
Abstract
Concentrations of aqueous-phase perfluorooctanoic acid (PFOA), a representative perfluorinated aliphatic (PFA) compound, are shown to be reduced effectively via reaction with horseradish peroxidase (HRP), hydrogen peroxide, and a phenolic cosubstrate (4-methoxyphenol). Reaction rate profiles are pseudo–first order, yielding an apparent best-fit removal rate constant of k1 = 0.003/min (r2 = 0.96, n = 14). Approximately 68% depletion of the parent compound and 98% depletion of its related acute aquatic toxicity are achieved in 6 h. Because no PFOA removal is observed in the absence of cosubstrate and/or following consumption thereof, we conclude that radical intermediate species generated during reaction between HRP and 4-methoxyphenol mediate nonspecific depletion of PFOA and that these intermediates may be sufficiently reactive to sever the extremely stable C–F bonds of PFOA. These results are consistent with measurements of reaction by-products, including fluoride ion and various aliphatic species of shortened chain length. Based on these findings, we conclude that PFA degradation may occur via one of two mechanisms: Kolbe decarboxylation followed by stepwise conversion of–CF2 units to CO2 and fluoride ion, or radical abstraction from a double bond with subsequent fragmentation. Our results indicate that under appropriate conditions, enzymatic degradation may comprise a natural transformation pathway for PFAs. Moreover, we anticipate that appropriately engineered enzymatic processes may hold promise for treatment of PFOA-contaminated waters. This, to the best of our knowledge, is the first report to substantiate the efficacy of HRP-catalyzed reactions for contaminant removal via degradative reactions versus polymerization reactions.
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“Accompanied by PFOA degradation, fluoride ions (less than 1%) and various short-chain fluorinated compounds were identified via ion chromatography and gas chromatography-mass spectrometry, respectively.”
From Toward the development of a molecular toolkit for the microbial remediation of per-and polyfluoroalkyl substances (2024) · cites this paper as [140]
In the citing paper
“Colosi et al. (140) first reported the effectiveness of HRP-mediated degradation of PFOA.”
From Toward the development of a molecular toolkit for the microbial remediation of per-and polyfluoroalkyl substances (2024) · cites this paper as [140]
In the citing paper
“Interactions between HRP and phenolic substrates facilitate the generation of highly reactive radical intermediates, enabling catalysis of secondary reactions with diverse organic contaminants (140).”
From Toward the development of a molecular toolkit for the microbial remediation of per-and polyfluoroalkyl substances (2024) · cites this paper as [140]
In the citing paper
“However, there was a substantial imbalance in the released fluoride concentrations between the actual measured value (2 mg/L) and theoretical value (165 mg/L) (140), suggesting that further work is needed to understand this reaction at a mechanistic level.”
From Toward the development of a molecular toolkit for the microbial remediation of per-and polyfluoroalkyl substances (2024) · cites this paper as [140]
In the citing paper
“In reactions using HRP, H2O2, and 4-methoxyphenol (a phenolic co-substrate), approximately 68% removal of PFOA (initial concentration of 850 µM) was observed.”
From Toward the development of a molecular toolkit for the microbial remediation of per-and polyfluoroalkyl substances (2024) · cites this paper as [140]
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Research works printed but not linked: 25
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Metadata
- Authors
- Colosi, L. M., Pinto, R. A., Huang, Q., & Weber, W. J. J.
- Affiliations
- Department of Civil and Environmental Engineering, University of Virginia, Charlottesville, Virginia 22904, USA
- Department of Chemical Engineering, University of Michigan, Ann Arbor, Michigan 48109, USA
- Department of Crop and Soil Sciences, University of Georgia, Griffin, Georgia 30223, USA
- Venue
- Environmental Toxicology and Chemistry
- Publisher
- Oxford University Press (OUP)
- Published
- 2009-02-01
- Volume
- 28
- Issue
- 2
- Pages
- 264-271
- ISSN
- 0730-7268
- 1552-8618
- Cited by
- 88
- References
- 0
- Language
- en
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