Anaerobic biodegradation of 8:2 fluorotelomer alcohol in anaerobic activated sludge: Metabolic products and pathways

Li, Fēi; Su, Qiangfa; Zhou, Zhenming; Liao, Xiaobin; Zou, Jing; Yuan, Baoling; Sun, Wenjie

doi:10.1016/j.chemosphere.2018.02.065

Cited by 56 publications

(38 citation statements)

References 51 publications

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“…Collectively, the cleavage of the first C–F bond in a perfluorinated structure is more critical and of greater significance given the recalcitrance of perfluorinated structures to biodegradation. Our findings suggest that the presence of the CC bond in a perfluorinated structure plays a crucial role in initiating the first C–F bond cleavage, which can result in the formation of polyfluorinated structures with C–H bond(s) that are more vulnerable to attack by other environmental microorganisms under aerobic or anaerobic conditions. ,, …”

Section: Resultsmentioning

confidence: 87%

“…Our findings suggest that the presence of the CC bond in a perfluorinated structure plays a crucial role in initiating the first C−F bond cleavage, which can result in the formation of polyfluorinated structures with C−H bond(s) that are more vulnerable to attack by other environmental microorganisms under aerobic or anaerobic conditions. 21,53,54 Microbial Reductive Defluorination Capabilities of the Identified Dehalorespiring Microorganisms in the Community. The dominant dehalorespiring microorganism in the investigated KB-1 culture is Dehalococcoides spp.. 55 The versatility of B 12 -dependent reductive dehalogenases of Dehalococcoides spp.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

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Microbial Cleavage of C–F Bonds in Two C₆ Per- and Polyfluorinated Compounds via Reductive Defluorination

Zhang

et al. 2020

Environ. Sci. Technol.

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The C−F bond is one of the strongest single bonds in nature. Although microbial reductive dehalogenation is well known for the other organohalides, no microbial reductive defluorination has been documented for perfluorinated compounds except for a single, nonreproducible study on trifluoroacetate. Here, we report on C−F bond cleavage in two C 6 perand polyfluorinated compounds via reductive defluorination by an organohalide-respiring microbial community. The reductive defluorination was demonstrated by the release of F − and the formation of the corresponding product when lactate was the electron donor, and the fluorinated compound was the sole electron acceptor. The major dechlorinating species in the seed culture, Dehalococcoides, were not responsible for the defluorination as no growth of Dehalococcoides or active expression of Dehalococcoides-reductive dehalogenases was observed. It suggests that minor phylogenetic groups in the community might be responsible for the reductive defluorination. These findings expand our fundamental knowledge of microbial reductive dehalogenation and warrant further studies on the enrichment, identification, and isolation of responsible microorganisms and enzymes. Given the wide use and emerging concerns of fluorinated organics (e.g., perand polyfluoroalkyl substances), particularly the perfluorinated ones, the discovery of microbial defluorination under common anaerobic conditions may provide valuable insights into the environmental fate and potential bioremediation strategies of these notorious contaminants.

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Section: Resultsmentioning

confidence: 87%

Section: ■ Materials and Methodsmentioning

confidence: 99%

Microbial Cleavage of C–F Bonds in Two C₆ Per- and Polyfluorinated Compounds via Reductive Defluorination

Zhang

et al. 2020

Environ. Sci. Technol.

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“…3). Both pathways have been previously shown in the biotransformation of 8:2 and 6:2 fluorotelomeric alcohols/acids in anaerobic sludges (22,24). The HF elimination reactions may occur both abiotically and biologically (mediated by enzymes like acyl-CoA dehydrogenases) (36).…”

mentioning

confidence: 81%

“…However, regarding typical PFASs with carbon chains longer than TFA, microbial defluorination has only been observed for telomeric structures (with -CH2 groups on the carbon backbone) and their polymers rather than perfluorinated ones (20)(21)(22)(23)(24). Fluorotelomer alcohols (FTOHs), carboxylic acids (FTCAs) and sulfonic acids (FTSAs) are all found to be partially biotransformed into perfluoroalkyl acids (PFAAs) under both aerobic and anaerobic conditions, suggesting potential sources of PFAAs (25,26).…”

mentioning

confidence: 99%

Microbial Cleavage of C‒F Bonds in Per- and Polyfluoroalkyl Substances via Dehalorespiration

Yu¹,

Zhang²,

Li³

et al. 2019

Preprint

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Regarding the emerging concerns of the widely occurred and environmentally persistent per- and polyfluoroalkyl substances (PFASs), one intriguing and unsolved scientific question for environmental microbiologists, chemists, and engineers is that whether microbial reductive defluorination of perfluorinated compounds exist in nature. Due to the strong dissociation energy of carbon‒fluorine (C‒F) bonds in PFASs, no convincing evidence for biological cleavage of C‒F bonds from > C<sub>2</sub> perfluorinated structures has ever been reported. We for the first time show C‒F bond cleavage via reductive defluorination by an organohalide-respiring microbial community for two PFASs, perfluoro(4-methylpent-2-enoic acid) and 4,5,5,5-tetrafluoro-4-(trifluoromethyl)-2-pentenoic acid. Comprehensive biotransformation pathways are further elucidated. This study brings valuable fundamental knowledge of microbial dehalorespiration, which opens avenues for the future exploration of PFAS environmental fate and bioremediation strategies.

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“…An exhaustive review of these mechanisms is beyond the scope of this study, but the reader can find substantial additional details in Liu and Avendaño (2013), Avendaño and Liu (2015), Wang et al (2009), Zhang et al (2013), andLi et al (2018).…”

Section: Introductionmentioning

confidence: 99%

Modeling PFAS Fate and Transport in Groundwater, with and Without Precursor Transformation

Gefell¹,

Huang²,

Opdyke

et al. 2021

Groundwater

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Groundwater professionals require tools to evaluate a variety of technical issues related to per-and polyfluoroalkyl substances (PFAS). These include the potential impact of PFAS precursors on groundwater plumes of perfluoroalkyl acids (PFAAs). Numerical modeling results show that, by adjusting the mass loading rate, source zones with or without a precursor can produce similar PFAA plumes. However, if a precursor is present, it can impact PFAA plume concentrations and extend PFAA plume durations by decades. Additional research regarding in situ precursor transformation rates-and improvements in source area characterization-will further advance the predictive value of modeling.

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Anaerobic biodegradation of 8:2 fluorotelomer alcohol in anaerobic activated sludge: Metabolic products and pathways

Cited by 56 publications

References 51 publications

Microbial Cleavage of C–F Bonds in Two C₆ Per- and Polyfluorinated Compounds via Reductive Defluorination

Microbial Cleavage of C–F Bonds in Two C₆ Per- and Polyfluorinated Compounds via Reductive Defluorination

Microbial Cleavage of C‒F Bonds in Per- and Polyfluoroalkyl Substances via Dehalorespiration

Modeling PFAS Fate and Transport in Groundwater, with and Without Precursor Transformation

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Anaerobic biodegradation of 8:2 fluorotelomer alcohol in anaerobic activated sludge: Metabolic products and pathways

Cited by 56 publications

References 51 publications

Microbial Cleavage of C–F Bonds in Two C6 Per- and Polyfluorinated Compounds via Reductive Defluorination

Microbial Cleavage of C–F Bonds in Two C6 Per- and Polyfluorinated Compounds via Reductive Defluorination

Microbial Cleavage of C‒F Bonds in Per- and Polyfluoroalkyl Substances via Dehalorespiration

Modeling PFAS Fate and Transport in Groundwater, with and Without Precursor Transformation

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Product

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Microbial Cleavage of C–F Bonds in Two C₆ Per- and Polyfluorinated Compounds via Reductive Defluorination

Microbial Cleavage of C–F Bonds in Two C₆ Per- and Polyfluorinated Compounds via Reductive Defluorination