The DOI matches its Crossref record; 5 of the 5 references it cites were found in a registry or an index.
Pseudomonas sp. Strain 273 Degrades Fluorinated Alkanes
Abstract
Fluorinated organic compounds have emerged as environmental constituents of concern. We demonstrate that the alkane degrader Pseudomonas sp. strain 273 utilizes terminally monofluorinated C7–C10 alkanes and 1,10-difluorodecane (DFD) as the sole carbon and energy sources in the presence of oxygen. Strain 273 degraded 1-fluorodecane (FD) (5.97 ± 0.22 mM, nominal) and DFD (5.62 ± 0.13 mM, nominal) within 7 days of incubation, and 92.7 ± 3.8 and 90.1 ± 1.9% of the theoretical maximum amounts of fluorine were recovered as inorganic fluoride, respectively. With n-decane, strain 273 attained (3.24 ± 0.14) × 107 cells per μmol of carbon consumed, while lower biomass yields of (2.48 ± 0.15) × 107 and (1.62 ± 0.23) × 107 cells were measured with FD or DFD as electron donors, respectively. The organism coupled decanol and decanoate oxidation to denitrification, but the utilization of (fluoro)alkanes was strictly oxygen-dependent, presumably because the initial attack on the terminal carbon requires oxygen. Fluorohexanoate was detected as an intermediate in cultures grown with FD or DFD, suggesting that the initial attack on the fluoroalkanes can occur on the terminal methyl or fluoromethyl groups. The findings indicate that specialized bacteria such as Pseudomonas sp. strain 273 can break carbon–fluorine bonds most likely with oxygenolytic enzyme systems and that terminally monofluorinated alkanes are susceptible to microbial degradation. The findings have implications for the fate of components associated with aqueous film-forming foam (AFFF) mixtures.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
In the citing paper
“Recently, bacterial degradation of monofluorinated alkyl chains via oxygenase‐initiated reactions was reported”
From Nothing lasts forever: understanding microbial biodegradation of polyfluorinated compounds and perfluorinated alkyl substances (2022) · cites this paper as Xie et al., 2020
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
Novel treatment technologies for PFAS compounds: A critical review
Kucharzyk, K. H., Darlington, R., Benotti, M., Deeb, R., & Hawley, E. (2017) · Journal of Environmental Management · doi:10.1016/j.jenvman.2017.08.016 · Cited by 562
Huang, S., & Jaffé, P. R. (2019) · Environmental Science & Technology · doi:10.1021/acs.est.9b04047 · Cited by 524
Per- and polyfluorinated substances (PFASs): Environmental challenges
Krafft, M. P., & Riess, J. G. (2015) · Current Opinion in Colloid & Interface Science · doi:10.1016/j.cocis.2015.07.004 · Cited by 294
Defluorination of Organofluorine Sulfur Compounds by Pseudomonas Sp. Strain D2
Key, B. D., Howell, R. D., & Criddle, C. S. (1998) · Environmental Science & Technology · doi:10.1021/es9800129 · Cited by 209
Borg, D., Lund, B.-O., Lindquist, N.-G., & Håkansson, H. (2013) · Environment International · doi:10.1016/j.envint.2013.05.009 · Cited by 155
Research works printed but not linked: 69
- Prevedouros, 2006, Sources, fate and transport of perfluorocarboxylates, Environ. Sci. Technol., 40, 32, 10.1021/es0512475 · DOI · Paper page
- Key, 1997, Fluorinated organics in the biosphere, Environ. Sci. Technol., 31, 2445, 10.1021/es961007c · DOI · Paper page
- Lewandowski, 2006, Special applications of fluorinated organic compounds, J. Hazard. Mater., 136, 385, 10.1016/j.jhazmat.2006.04.017 · DOI
- Müller, 2007, Fluorine in pharmaceuticals: looking beyond intuition, Science, 317, 1881, 10.1126/science.1131943 · DOI
- Dassuncao, 2019, Phospholipid levels predict the tissue distribution of poly- and perfluoroalkyl substances in a marine mammal, Environ. Sci. Technol. Lett., 6, 119, 10.1021/acs.estlett.9b00031 · DOI
- Ross, 2018, A review of emerging technologies for remediation of PFASs, Rem. J., 28, 101, 10.1002/rem.21553 · DOI · Paper page
- Isidorov, 1990, Volatile organic compounds in solfataric gases, J. Atmos. Chem., 10, 329, 10.1007/BF00053867 · DOI
- Jordan, 2003, Volcanic formation of halogenated organic compounds, 121, 10.1007/b10450 · DOI
- Jordan, 2000, Volcanogenic halocarbons, Environ. Sci. Technol., 34, 1122, 10.1021/es990838q · DOI
- Zechel, 2001, Enzymatic synthesis of carbon – fluorine bonds, J. Am. Chem. Soc., 123, 4350, 10.1021/ja005855q · DOI
- Dong, 2004, Crystal structure and mechanism of a bacterial fluorinating enzym, Nature, 427, 561, 10.1038/nature02280 · DOI · Paper page
- Walker, 2013, Expanding the fluorine chemistry of living systems using engineered polyketide synthase pathways, Science, 341, 1089, 10.1126/science.1242345 · DOI
- O’Hagan, 2015, Enzymatic fluorination and biotechnological developments of the fluorinase, Chem. Rev., 115, 634, 10.1021/cr500209t · DOI · Paper page
- Carvalho, 2017, Natural production of fluorinated compounds and biotechnological prospects of the fluorinase enzyme, Crit. Rev. Biotechnol., 37, 880, 10.1080/07388551.2016.1267109 · DOI · Paper page
- Lemal, 2004, Perspective on fluorocarbon chemistry, J. Org. Chem., 69, 1, 10.1021/jo0302556 · DOI
- Harper, 1994, The fluorinated natural products, Nat. Prod. Rep., 11, 123, 10.1039/NP9941100123 · DOI
- Natarajan, 2005, Microbial cleavage of C-F bond, J. Fluorine Chem., 126, 424, 10.1016/j.jfluchem.2004.12.001 · DOI
- Murphy, 2016, Microbial degradation of fluorinated drugs: biochemical pathways, impacts on the environment and potential applications, Appl. Microbiol. Biotechnol., 100, 2617, 10.1007/s00253-016-7304-3 · DOI
- Kiel, 2015, The biodegradation vs. biotransformation of fluorosubstituted aromatics, Appl. Microbiol. Biotechnol., 99, 7433, 10.1007/s00253-015-6817-5 · DOI · Paper page
- Goldman, 1966, Carbon-fluorine bond cleavage. II. Studies on the mechanism of the defluorination of fluoroacetate, J. Biol. Chem., 241, 5557, 10.1016/S0021-9258(18)96379-9 · DOI
- Schennen, 1985, Anaerobic degradation of 2-fluorobenzoate by benzoate-degrading, denitrifying bacteria, J. Bacteriol., 161, 321, 10.1128/JB.161.1.321-325.1985 · DOI
- Vargas, 2000, Anaerobic degradation of fluorinated aromatic compounds, Appl. Microbiol. Biotechnol., 53, 342, 10.1007/s002530050032 · DOI
- Tiedt, 2016, ATP-dependent C-F bond cleavage allows the complete degradation of 4-fluoroaromatics without oxygen, MBio, 7, 10.1128/mBio.00990-16 · DOI · Paper page
- Tiedt, 2017, Promiscuous defluorinating enoyl-CoA hydratases/hydrolases allow for complete anaerobic degradation of 2-fluorobenzoate, Front. Microbiol., 8, 2579, 10.3389/fmicb.2017.02579 · DOI · Paper page
- 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
- Parsons, 2008, Biodegradation of perfluorinated compounds, Rev. Environ. Contam. Toxicol., 196, 53, 10.1007/978-0-387-78444-1_2 · DOI · Paper page
- 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
- Kurihara, 2003, Purification, characterization, and gene cloning of a novel fluoroacetate dehalogenase from Burkholderia sp. FA1, J. Mol. Catal. B: Enzym., 23, 347, 10.1016/S1381-1177(03)00098-5 · DOI · Paper page
- Im, 2019, Biotic and abiotic dehalogenation of 1, 1, 2-trichloro-1, 2, 2-trifluoroethane (CFC-113): implications for bacterial detoxification of chlorinated ethenes, Environ. Sci. Technol., 53, 11941, 10.1021/acs.est.9b04399 · DOI
- Yan, 2018, Purinyl-cobamide is a native prosthetic group of reductive dehalogenases, Nat. Chem. Biol., 14, 8, 10.1038/nchembio.2512 · DOI
- Ochoa-Herrera, 2008, Reductive defluorination of perfluorooctane sulfonate, Environ. Sci. Technol., 42, 3260, 10.1021/es702842q · DOI · Paper page
- 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
- 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
- Chang, 1995, Biotransformation of HCFC-22, HCFC-142b, HCFC-123, and HFC-134a by methanotrophic mixed culture MM1, Biodegradation, 6, 1, 10.1007/BF00702293 · DOI
- Oltmanns, 1989, Evidence for a new pathway in the bacterial degradation of 4-fluorobenzoate, Appl. Environ. Microbiol., 55, 2499, 10.1128/AEM.55.10.2499-2504.1989 · DOI
- Shen, 2015, Review of recent advances in C-F bond activation of aliphatic fluorides, J. Fluorine Chem., 179, 14, 10.1016/j.jfluchem.2015.07.007 · DOI
- Dembitsky, 2002, Natural halogenated fatty acids: their analogues and derivatives, Prog. Lipid Res., 41, 315, 10.1016/S0163-7827(02)00003-6 · DOI
- Igwe, 2015, Chemical analyses of volatile compounds from cuticular and non-cuticular abdominal glands of African weaver ants (Oecophylla longinoda), Chem. Sci. Int. J., 5, 304, 10.9734/ACSJ/2015/14255 · DOI
- 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
- Blotevogel, 2018, Reductive defluorination of perfluorooctanoic acid by zero-valent iron and zinc: A DFT-based kinetic model, Chem. Eng. J., 335, 248, 10.1016/j.cej.2017.10.131 · DOI
- 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
- Singh, 2019, Breakdown products from perfluorinated alkyl substances (PFAS) degradation in a plasma-based water treatment process, Environ. Sci. Technol., 53, 2731, 10.1021/acs.est.8b07031 · DOI · Paper page
- Tseng, 2014, Biotransformation of 6: 2 fluorotelomer alcohol (6: 2 FTOH) by a wood-rotting fungus, Environ. Sci. Technol., 48, 4012, 10.1021/es4057483 · DOI · Paper page
- Luo, 2015, Laccase-catalyzed degradation of perfluorooctanoic acid, Environ. Sci. Technol. Lett., 2, 198, 10.1021/acs.estlett.5b00119 · DOI · Paper page
- Wischnak, 1998, Pseudomonas sp. strain 273, an aerobic α,ω-dichloroalkane-degrading bacterium, Appl. Environ. Microbiol., 64, 3507, 10.1128/AEM.64.9.3507-3511.1998 · DOI
- Heath, 2006, Biodegradation of chlorinated alkanes and their commercial mixtures by Pseudomonas sp. strain 273, J. Ind. Microbiol. Biotechnol., 33, 197, 10.1007/s10295-004-0186-x · DOI
- Fetzner, 2010, Aerobic degradation of halogenated aliphatics, 865, 10.1007/978-3-540-77587-4_62 · DOI
- Wolin, 1963, Formation of methane by bacterial extracts, J. Biol. Chem., 238, 2882, 10.1016/S0021-9258(18)67912-8 · DOI
- Yoshinari, 1976, Acetylene inhibition of nitrous oxide reduction by denitrifying bacteria, Biochem. Biophys. Res. Commun., 69, 705, 10.1016/0006-291X(76)90932-3 · DOI
- Ye, 2012, Primer-BLAST: a tool to design target-specific primers for polymerase chain reaction, BMC Bioinf., 13, 134, 10.1186/1471-2105-13-134 · DOI
- Powers, 2019, Design and evaluation of a gas chromatograph-atmospheric pressure chemical ionization interface for an exactive orbitrap mass spectrometer, J. Am. Soc. Mass Spectrom., 30, 2369, 10.1007/s13361-019-02311-6 · DOI
- Rojo, 2009, Degradation of alkanes by bacteria, Environ. Microbiol., 11, 2477, 10.1111/j.1462-2920.2009.01948.x · DOI
- Belkin, 1992, Biodegradation of haloalkanes, Biodegradation, 3, 299, 10.1007/BF00129090 · DOI
- Scholtz, 1987, Degradation of eighteen 1-monohaloalkanes by Arthrobacter sp. strain HA1, Microbiology, 133, 267, 10.1099/00221287-133-2-267 · DOI
- Curragh, 1994, Haloalkane degradation and assimilation by Rhodococcus rhodochrous NCIMB 13064, Microbiology, 140, 1433, 10.1099/00221287-140-6-1433 · DOI
- Van Beilen, 2007, Alkane hydroxylases involved in microbial alkane degradation, Appl. Microbiol. Biotechnol., 74, 13, 10.1007/s00253-006-0748-0 · DOI
- Koe, 1993, Dehalogenation by cytochrome P-450cam: Effect of oxygen level on the decomposition of 1, 2-dibromo-3-chloropropane, Biotechnol. Prog., 9, 608, 10.1021/bp00024a007 · DOI
- Gribble, 1973, Fluoroacetate toxicity, J. Chem. Educ., 50, 460, 10.1021/ed050p460 · DOI
- Chidthaisong, 2000, Specificity of chloroform, 2-bromoethanesulfonate and fluoroacetate to inhibit methanogenesis and other anaerobic processes in anoxic rice field soil, Soil Biol. Biochem., 32, 977, 10.1016/S0038-0717(00)00006-7 · DOI
- Goldman, 1969, The carbon-fluorine bond in compounds of biological interest, Science, 164, 1123, 10.1126/science.164.3884.1123 · DOI
- Kunz, 1983, Bacterial formation and metabolism of 6-hydroxyhexanoate: evidence of a potential role for omega-oxidation, J. Bacteriol., 156, 567, 10.1128/JB.156.2.567-575.1983 · DOI
- Peterson, 1967, Enzymatic ω-oxidation II. Function of rubredoxin as the electron carrier in ω-hydroxylation, J. Biol. Chem., 242, 4334, 10.1016/S0021-9258(18)99543-8 · DOI
- McKenna, 1970, Enzymatic ω-oxidation IV. Purification and properties of the ω-hydroxylase of Pseudomonas oleovorans, J. Biol. Chem., 245, 3882, 10.1016/S0021-9258(18)62932-1 · DOI
- Maier, 2000, Pseudomonas aeruginosa rhamnolipids: biosynthesis and potential applications, Appl. Microbiol. Biotechnol., 54, 625, 10.1007/s002530000443 · DOI
- Zhang, 2012, Isolation and identification of biosurfactant producing and crude oil degrading Pseudomonas aeruginosa strains, Chem. Eng. J., 209, 138, 10.1016/j.cej.2012.07.110 · DOI
- Zhang, 1995, Effect of rhamnolipid (biosurfactant) structure on solubilization and biodegradation of n-alkanes, Appl. Environ. Microbiol., 61, 2247, 10.1128/AEM.61.6.2247-2251.1995 · DOI
- Hamilton, 1990, Biochemical effects of fluoride on oral bacteria, J. Dent. Res., 69, 660, 10.1177/00220345900690S128 · DOI · Paper page
- Luo, 2018, Perfluorooctanesulfonate degrades in a laccase-mediator system, Environ. Sci. Technol., 52, 10617, 10.1021/acs.est.8b00839 · DOI · Paper page
- Nzeribe, 2019, Physico-chemical processes for the treatment of per- and polyfluoroalkyl Substances (PFAS): A review, Crit. Rev. Environ. Sci. Technol., 49, 866, 10.1080/10643389.2018.1542916 · DOI · Paper page
Cited by
Sorted by citations
Wackett, L. P. (2022) · Microbial Biotechnology · doi:10.1111/1751-7915.13928 · Cited by 165
Stockbridge, R. B., & Wackett, L. P. (2024) · Nature Communications · doi:10.1038/s41467-024-49018-1 · Cited by 80
Dodge, A. G., Thoma, C. J., O’Connor, M. R., & Wackett, L. P. (2024) · mBio · doi:10.1128/mbio.02785-23 · Cited by 23
Metadata
- Authors
- Xie, Y., Chen, G., May, A. L., Yan, J., Brown, L. P., Powers, J. B., Campagna, S. R., & Löffler, F. E.
- Affiliations
- University of Tennessee , , , ,
- Chinese Academy of Sciences , , , ,
- ORCID
- Löffler, Frank E.
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2020-11-16
- Volume
- 54
- Issue
- 23
- Pages
- 14994-15003
- ISSN
- 0013-936X
- 1520-5851
- Cited by
- 48
- References
- 5
- Language
- en
- Licence
- Funders
- China Scholarship Council
- University Consortium for Field-Focused Groundwater Research
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review