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Microbial Cleavage of C–F Bonds in Two C6 Per- and Polyfluorinated Compounds via Reductive Defluorination
Abstract
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 C6 per- and 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., per- and 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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Defluorination of perfluorinated acids has been reported in consortia and by a single bacterium.
“Biological systems that degrade perfluorinated compounds have also been reported recently44,45, including reports of the defluorination of perfluorinated acids in consortia46–48 and by a single bacterium49.”
From The link between ancient microbial fluoride resistance mechanisms and bioengineering organofluorine degradation or synthesis (2024) · cites this paper as [46]
The previously reported defluorination of FTMeUPA at the tertiary C─F by the anaerobic community should be attributed to other pathways with different mechanisms.
“Thus, the previously reported defluorination of FTMeUPA at the tertiary C─F by the anaerobic community (17) should be attributed to other pathways with different mechanisms.”
From Electron bifurcation and fluoride efflux systems implicated in defluorination of perfluorinated unsaturated carboxylic acids by Acetobacterium spp (2024) · cites this paper as [17]
The defluorination by A. bakii was substantially faster than previously reported (~120 days) in the anaerobic community.
“The defluorination was substantially faster than that reported previously (~120 days) in the anaerobic community (17).”
From Electron bifurcation and fluoride efflux systems implicated in defluorination of perfluorinated unsaturated carboxylic acids by Acetobacterium spp (2024) · cites this paper as [17]
Previous studies observed reductive defluorination of PFMeUPA by an anaerobic microbial community grown on lactate.
“In previous studies, we observed reductive defluorination of an unsaturated perfluorinated compound, E-perfluoro-4-methylpent-2-enoic acid [PFMeUPA, (CF3)2CFCF═CFCOOH], by an anaerobic microbial community grown on lactate (17).”
From Electron bifurcation and fluoride efflux systems implicated in defluorination of perfluorinated unsaturated carboxylic acids by Acetobacterium spp (2024) · cites this paper as [17]
The defluorination of PFMeUPA by the anaerobic community was not catalyzed by Dehalococcoides.
“The defluorination was not catalyzed by Dehalococcoides, capable of reductive dechlorination, in the community (17).”
From Electron bifurcation and fluoride efflux systems implicated in defluorination of perfluorinated unsaturated carboxylic acids by Acetobacterium spp (2024) · cites this paper as [17]
The accuracy of fluoride ion measurement by ion-selective electrode was cross-validated using ion chromatography.
“The accuracy of the fluoride measurement by ISE was cross-validated using ion chromatography as described in our previous study (17).”
From Electron bifurcation and fluoride efflux systems implicated in defluorination of perfluorinated unsaturated carboxylic acids by Acetobacterium spp (2024) · cites this paper as [17]
In 2020, Yu et al. inferred the reductive defluorination of two C6 unsaturated and branched fluorinated compounds by a Dehalococcoides-containing trichloroethene-dechlorinating consortium (KB1).
“In 2020, Yu et al. (107) inferred the reductive defluorination of two C6 unsaturated and branched fluorinated compounds by a Dehalococcoides-containing trichloroethene-dechlorinating consortium (KB1).”
From Toward the development of a molecular toolkit for the microbial remediation of per-and polyfluoroalkyl substances (2024) · cites this paper as [107]
No gene transcription of reductive dehalogenases in KB-1 was observed during the defluorination of fluorinated compounds.
“Regarding reductive defluorinases, no gene transcription of reductive dehalogenases in KB-1 was observed during the defluorination of fluorinated compounds (107).”
From Toward the development of a molecular toolkit for the microbial remediation of per-and polyfluoroalkyl substances (2024) · cites this paper as [107]
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Cites
Effect of the damping function in dispersion corrected density functional theory
Grimme, S., Ehrlich, S., & Goerigk, L. (2011) · Journal of Computational Chemistry · doi:10.1002/jcc.21759 · Cited by 28,221
Identifying Small Molecules via High Resolution Mass Spectrometry: Communicating Confidence
Schymanski, E. L., Jeon, J., Gulde, R., Fenner, K., Ruff, M., Singer, H. P., & Hollender, J. (2014) · Environmental Science & Technology · doi:10.1021/es5002105 · Cited by 4,519
A Never-Ending Story of Per- and Polyfluoroalkyl Substances (PFASs)?
Wang, Z., DeWitt, J. C., Higgins, C. P., & Cousins, I. T. (2017) · Environmental Science & Technology · doi:10.1021/acs.est.6b04806 · Cited by 1,921
Microbial degradation of polyfluoroalkyl chemicals in the environment: A review
Liu, J., & Mejia Avendaño, S. (2013) · Environment International · doi:10.1016/j.envint.2013.08.022 · Cited by 525
Self-citationHuang, S., & Jaffé, P. R. (2019) · Environmental Science & Technology · doi:10.1021/acs.est.9b04047 · Cited by 524
Degradation and Removal Methods for Perfluoroalkyl and Polyfluoroalkyl Substances in Water
Merino, N., Qu, Y., Deeb, R. A., Hawley, E. L., Hoffmann, M. R., & Mahendra, S. (2016) · Environmental Engineering Science · doi:10.1089/ees.2016.0233 · Cited by 349
Fluorotelomer Alcohol BiodegradationDirect Evidence that Perfluorinated Carbon Chains Breakdown
Wang, N., Szostek, B., Buck, R. C., Folsom, P. W., Sulecki, L. M., Capka, V., Berti, W. R., & Gannon, J. T. (2005) · Environmental Science & Technology · doi:10.1021/es0506760 · Cited by 260
Lindstrom, A. B., Strynar, M. J., Delinsky, A. D., Nakayama, S. F., McMillan, L., Libelo, E. L., Neill, M., & Thomas, L. (2011) · Environmental Science & Technology · doi:10.1021/es1039425 · Cited by 227
Zhang, S., Szostek, B., McCausland, P. K., Wolstenholme, B. W., Lu, X., Wang, N., & Buck, R. C. (2013) · Environmental Science & Technology · doi:10.1021/es4000824 · Cited by 198
Bao, Y., Qu, Y., Huang, J., Cagnetta, G., Yu, G., & Weber, R. (2017) · RSC Adv. · doi:10.1039/c7ra09728j · Cited by 104
Washington, J. W., Jenkins, T. M., & Weber, E. J. (2015) · Environmental Science & Technology · doi:10.1021/acs.est.5b03379 · Cited by 50
Flagged first, then by citations
Research works printed but not linked: 53
- Im, 2014, Environmental fate of the next generation refrigerant 2,3,3,3-tetrafluoropropene (HFO-1234yf), Environ. Sci. Technol., 48, 13181, 10.1021/es5032147 · DOI
- Furuya, 2011, Catalysis for fluorination and trifluoromethylation, Nature, 473, 470, 10.1038/nature10108 · DOI
- Xiao, 2017, Emerging poly- and perfluoroalkyl substances in the aquatic environment: a review of current literature, Water Res., 124, 482, 10.1016/j.watres.2017.07.024 · DOI · Paper page
- Sun, 2016, Legacy and emerging perfluoroalkyl substances are important drinking water contaminants in the Cape Fear River watershed of North Carolina, Environ. Sci. Technol. Lett., 3, 415, 10.1021/acs.estlett.6b00398 · DOI · Paper page
- Key, 1997, Fluorinated organics in the biosphere, Environ. Sci. Technol., 31, 2445, 10.1021/es961007c · DOI · Paper page
- Liu, 2018, Reductive defluorination of branched per- and polyfluoroalkyl substances with cobalt complex catalysts, Environ. Sci. Technol. Lett., 5, 289, 10.1021/acs.estlett.8b00122 · DOI · Paper page
- Bentel, 2019, Defluorination of per- and polyfluoroalkyl substances (PFASs) with hydrated electrons: structural dependence and implications to PFAS remediation and management, Environ. Sci. Technol., 53, 3718, 10.1021/acs.est.8b06648 · DOI
- Bentel, 2020, Degradation of perfluoroalkyl ether carboxylic acids with hydrated electrons: structure-reactivity relationships and environmental implications, Environ. Sci. Technol., 54, 2489, 10.1021/acs.est.9b05869 · DOI
- Bentel, 2020, Enhanced degradation of perfluorocarboxylic acids (PFCAs) by UV/Sulfite treatment: reaction mechanisms and system efficiencies at pH 12, Environ. Sci. Technol. Lett., 7, 351, 10.1021/acs.estlett.0c00236 · DOI
- Goldman, 1965, The enzymatic cleavage of the carbon-fluorine bond in fluoroacetate, J. Biol. Chem., 240, 3434, 10.1016/S0021-9258(18)97236-4 · DOI · Paper page
- Visscher, 1994, Degradation of trifluoroacetate in oxic and anoxic sediments, Nature, 369, 729, 10.1038/369729a0 · DOI · Paper page
- Kim, 2000, Biodegradability of trifluoroacetic acid, Environ. Eng. Sci., 17, 337, 10.1089/ees.2000.17.337 · DOI · Paper page
- Oremland, R. S.; Matheson, L. J.; Guidetti, J. R.; Schaefer, J. K.; Visscher, P. T. Summary of research results on bacterial degradation of trifluoroacetate (TFA), November, 1994-May, 1995; Open-File Report, 1995; Vol. 95–422. · DOI
- Davis, 2012, Isolation and survey of novel fluoroacetate-degrading bacteria belonging to the phylum Synergistetes, FEMS Microbiol. Ecol., 80, 671, 10.1111/j.1574-6941.2012.01338.x · DOI · Paper page
- Leong, 2016, Amino acid and peptide utilization profiles of the fluoroacetate-degrading bacterium Synergistetes strain MFA1 under varying conditions, Microb. Ecol., 71, 494, 10.1007/s00248-015-0641-4 · DOI · Paper page
- Shaw, 2019, Degradation and defluorination of 6:2 fluorotelomer sulfonamidoalkyl betaine and 6:2 fluorotelomer sulfonate by Gordonia sp. strain NB4-1Y under sulfur-limiting conditions, Sci. Total Environ., 647, 690, 10.1016/j.scitotenv.2018.08.012 · DOI · Paper page
- Parsons, 2008, Biodegradation of perfluorinated compounds, 53
- Park, 2017, Alternate reductants with VB12 to transform C8 and C6 perfluoroalkyl sulfonates: limitations and insights into isomer specific transformation rates, products and pathways, Environ. Sci. Technol., 51, 13869, 10.1021/acs.est.7b03744 · DOI · Paper page
- Brown, 2005, Chemistry and enzymology of vitamin B12, Chem. Rev., 105, 2075, 10.1021/cr030720z · DOI
- Fincker, 2017, Biochemistry of catabolic reductive dehalogenation, Annu. Rev. Biochem., 86, 357, 10.1146/annurev-biochem-061516-044829 · DOI · Paper page
- Schubert, 2018, Organohalide respiratory chains: composition, topology and key enzymes, FEMS Microbiol. Ecol., 94, fiy035, 10.1093/femsec/fiy035 · DOI
- Holliger, 2004, Dehalogenation by anaerobic bacteria, 115, 10.1007/0-306-48011-5_5 · DOI
- Men, 2012, Sustainable syntrophic growth of Dehalococcoides ethenogenes strain 195 with Desulfovibrio vulgaris Hildenborough and Methanobacterium congolense: global transcriptomic and proteomic analyses, ISME J., 6, 410, 10.1038/ismej.2011.111 · DOI
- He, 2007, Influence of vitamin B12 and cocultures on the growth of Dehalococcoides isolates in defined medium, Appl. Environ. Microbiol., 73, 2847, 10.1128/aem.02574-06 · DOI
- Han, 2019, Specific micropollutant biotransformation pattern by the comammox bacterium Nitrospira inopinata, Environ. Sci. Technol., 53, 8695, 10.1021/acs.est.9b01037 · DOI
- Zhou, 2019, Cometabolic biotransformation and microbial-mediated abiotic transformation of sulfonamides by three ammonia oxidizers, Water Res., 159, 444, 10.1016/j.watres.2019.05.031 · DOI
- Yu, 2018, Ammonia monooxygenase-mediated cometabolic biotransformation and hydroxylamine-mediated abiotic transformation of micropollutants in an AOB/NOB coculture, Environ. Sci. Technol., 52, 9196, 10.1021/acs.est.8b02801 · DOI
- Men, 2016, Biotransformation of two pharmaceuticals by the ammonia-oxidizing archaeon Nitrososphaera gargensis, Environ. Sci. Technol., 50, 4682, 10.1021/acs.est.5b06016 · DOI
- Allen, 2014, CFM-ID: a web server for annotation, spectrum prediction and metabolite identification from tandem mass spectra, Nucleic Acids Res., 42, W94, 10.1093/nar/gku436 · DOI
- Miller, 1999, Comparison of gas-sampled and SPME-sampled static headspace for the determination of volatile flavor components, Anal. Chem., 71, 23, 10.1021/ac980576v · DOI
- Bourdin, 2014, Development of SPME on-fiber derivatization for the sampling of formaldehyde and other carbonyl compounds in indoor air, Anal. Bioanal. Chem., 406, 317, 10.1007/s00216-013-7460-6 · DOI
- Becke, 1993, Density-functional thermochemistry. III. The role of exact exchange, J. Chem. Phys., 98, 5648, 10.1063/1.464913 · DOI · Paper page
- Lee, 1988, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B: Condens. Matter Mater. Phys., 37, 785, 10.1103/physrevb.37.785 · DOI · Paper page
- Stephens, 1994, Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields, J. Phys. Chem., 98, 11623, 10.1021/j100096a001 · DOI
- Vosko, 1980, Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis, Can. J. Phys., 58, 1200, 10.1139/p80-159 · DOI
- Marenich, 2009, Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions, J. Phys. Chem. B, 113, 6378, 10.1021/jp810292n · DOI
- Men, 2014, Sustainable growth of Dehalococcoides mccartyi 195 by corrinoid salvaging and remodeling in defined lactate-fermenting consortia, Appl. Environ. Microbiol., 80, 2133, 10.1128/aem.03477-13 · DOI
- Livak, 2001, Analysis of relative gene expression data using real-time quantitative PCR and the 2‑ΔΔCT method, Methods, 25, 402, 10.1006/meth.2001.1262 · DOI · Paper page
- Baumgartner, 2012, Hydrodefluorination and hydrogenation of fluorobenzene under mild aqueous conditions, Environ. Sci. Technol., 46, 10199, 10.1021/es302188f · DOI
- Peterson, 2006, Catalytic dehalogenation of sp2 C-F and C-Cl bonds in fluoro- and chloroalkenes, Organometallics, 25, 4938, 10.1021/om0607292 · DOI
- Amii, 2009, C-F bond activation in organic synthesis, Chem. Rev., 109, 2119, 10.1021/cr800388c · DOI
- Tischer, 1979, Purification and some properties of a hitherto-unknown enzyme reducing the carbon-carbon double bond of α,β-unsaturated carboxylate anions, Eur. J. Biochem., 97, 103, 10.1111/j.1432-1033.1979.tb13090.x · DOI
- Winkler, 2012, Asymmetric bioreduction of activated alkenes to industrially relevant optically active compounds, J. Biotechnol., 162, 381, 10.1016/j.jbiotec.2012.03.023 · DOI
- Li, 2018, Anaerobic biodegradation of 8:2 fluorotelomer alcohol in anaerobic activated sludge: metabolic products and pathways, Chemosphere, 200, 124, 10.1016/j.chemosphere.2018.02.065 · DOI
- Wang, 2012, 5:3 Polyfluorinated acid aerobic biotransformation in activated sludge via novel “one-carbon removal pathways”, Chemosphere, 87, 527, 10.1016/j.chemosphere.2011.12.056 · DOI · Paper page
- Duhamel, 2006, Microbial composition of chlorinated ethene-degrading cultures dominated by Dehalococcoides, FEMS Microbiol. Ecol., 58, 538, 10.1111/j.1574-6941.2006.00191.x · DOI
- Löffler, 2015, Dehalococcoides mccartyi gen. nov., sp. nov., obligately organohalide-respiring anaerobic bacteria relevant to halogen cycling and bioremediation, belong to a novel bacterial class, Dehalococcoidia classis nov., order Dehalococcoidales ord. nov. and family Dehalococcoidaceae fam. nov., within the phylum Chloroflexi, Int. J. Syst. Evol. Microbiol., 63, 625, 10.1099/ijs.0.034926-0 · DOI
- Waller, 2005, Multiple reductive-dehalogenase-homologous genes are simultaneously transcribed during dechlorination by Dehalococcoides-containing cultures, Appl. Environ. Microbiol., 71, 8257, 10.1128/aem.71.12.8257-8264.2005 · DOI
- Puentes Jácome, 2017, A switch of chlorinated substrate causes emergence of a previously undetected native Dehalobacter population in an established Dehalococcoides-dominated chloroethene-dechlorinating enrichment culture, FEMS Microbiol. Ecol., 93, fix141, 10.1093/femsec/fix141 · DOI
- Nelson, 2014, Dehalogenation of chlorobenzenes, dichlorotoluenes, and tetrachloroethene by three Dehalobacter spp, Environ. Sci. Technol., 48, 3776, 10.1021/es4044769 · DOI
- Alfán-Guzmán, 2017, Isolation and characterization of Dehalobacter sp. strain TeCB1 including identification of TcbA: a novel tetra- and trichlorobenzene reductive dehalogenase, Front. Microbiol., 8, 558, 10.3389/fmicb.2017.00558 · DOI
- Rupakula, 2013, The restricted metabolism of the obligate organohalide respiring bacterium Dehalobacter restrictus: lessons from tiered functional genomics, Philos. Trans. R. Soc., B, 368, 20120325, 10.1098/rstb.2012.0325 · DOI
- Cousins, 2019, The concept of essential use for determining when uses of PFASs can be phased out, Environ. Sci.: Processes Impacts, 21, 1803, 10.1039/c9em00163h · DOI
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“Another hypothesis explaining this behaviour is that PFAAs broke down into shorter-chain PFAAs, which is not usual, but has been achieved in the laboratory under specific conditions (Huang & Jaff ´ e, 2019; Meesters & Schr ¨ oder, 2004; Visscher et al., 1994; Yu et al., 2020).”
Metadata
- Authors
- Yu, Y., Zhang, K., Li, Z., Ren, C., Chen, J., Lin, Y.-H., Liu, J., & Men, Y.
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2020-10-29
- Volume
- 54
- Issue
- 22
- Pages
- 14393-14402
- ISSN
- 0013-936X
- 1520-5851
- Cited by
- 167
- References
- 11
- Language
- en
- Licence
- Funders
- National Science Foundation (CHE-1709286, CHE-1709719)
- Strategic Environmental Research and Development Program (ER20-1541)
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