Desulfonation and defluorination of 6:2 fluorotelomer sulfonic acid (6:2 FTSA) by rhodococcus jostii RHA1: carbon and sulfur sources, enzymes, and pathways
Open accessAbstract
6:2 fluorotelomer sulfonic acid (6:2 FTSA) is one per- and poly-fluoroalkyl substances commonly detected in the environment. While biotransformation of 6:2 FTSA has been reported, factors affecting desulfonation and defluorination of 6:2 FTSA remain poorly understood. This study elucidated the effects of carbon and sulfur sources on the gene expression of Rhodococcus jostii RHA1 which is responsible for the 6:2 FTSA biotransformation. While alkane monooxygenase and cytochrome P450 were highly expressed in ethanol-, 1-butanol-, and n-octane-grown RHA1 in sulfur-rich medium, these cultures only defluorinated 6:2 fluorotelomer alcohol but not 6:2 FTSA, suggesting that the sulfonate group in 6:2 FTSA hinders enzymatic defluorination. In sulfur-free growth media, alkanesulfonate monooxygenase was linked to desulfonation of 6:2 FTSA; while alkane monooxygenase, haloacid dehalogenase, and cytochrome P450 were linked to defluorination of 6:2 FTSA. The desulfonation and defluorination ability of these enzymes toward 6:2 FTSA were validated through heterologous gene expression and in vitro assays. Four degradation metabolites were confirmed and one was identified as a tentative metabolite. The results provide a new understanding of 6:2 FTSA biotransformation by RHA1. The genes encoding these desulfonating- and defluorinating-enzymes are potential markers to be used to assess 6:2 FTSA biotransformation in the environment.
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Yang et al. (2022) investigated the effects of adding glucose, ethanol, n-octane and 1-butanol as carbon sources on biodegradation of 6:2 FTOH and 6:2 FTSA and reported different defluorination rates; the highest fluoride release was in 1-butanol for FTOH.
“Yang et al. (2022) investigated the effects of adding glucose, ethanol, n-octane and 1-butanol as carbon sources on biodegradation of 6:2 FTOH and 6:2 FTSA and reported different defluorination rates; the highest fluoride re- lease was in 1-butanol for FTOH.”
From A review of microbial degradation of per- and polyfluoroalkyl substances (PFAS): Biotransformation routes and enzymes (2023) · cites this paper as Yang et al. (2022)
Split into 2 atoms — 1 confirmed, 1 partially supported, 0 disputed, 0 misattributed, 0 unverifiable. Expand the claim to see per-atom verdicts.
Experimental — accuracy not yet measuredNo degradation of 6:2 FTSA was observed under sulfur-rich conditions with Rhodococcus jostii RHA1, but under S-limiting conditions, 99% was biotransformed through initial desulfonation and subsequent 6:2 FTOH degradation into two major metabolites (6:2 FTUCA and α-OH 5:3 FTCA) and minor metabolites (PFHpA and the transient 6:2 FTCA).
“No degradation of 6:2 FTSA was ob- served under sulfur-rich conditions with Rhodococcus jostii RHA1, but under S-limiting conditions, 99 % was biotransformed through initial desulfonation and subsequent 6:2 FTOH degradation into twomajor metab- olites (6:2 FTUCA and α-OH 5:3 FTCA) and minor metabolites (PFHpA and the transient 6:2 FTCA) (Yang et al., 2022).”
From A review of microbial degradation of per- and polyfluoroalkyl substances (PFAS): Biotransformation routes and enzymes (2023) · cites this paper as Yang et al., 2022
Split into 2 atoms — 1 confirmed, 1 partially supported, 0 disputed, 0 misattributed, 0 unverifiable. Expand the claim to see per-atom verdicts.
Experimental — accuracy not yet measuredDesulfonation of PFSAs is suspected to be catalyzed by alkanesulfonate monooxygenases, ssuDEABC proteins, haloacid dehalogenases, cytochrome P450s and nitriloacetate monooxygenases.
“is suspected to be catalyzed by alkanesulfonate monooxygenases, ssuDEABC proteins, haloacid dehalogenases, cytochrome P450s and nitriloacetate monooxygenases (Table 4) (Méndez et al., 2022; Van Hamme et al., 2013; Yang et al., 2022)”
From A review of microbial degradation of per- and polyfluoroalkyl substances (PFAS): Biotransformation routes and enzymes (2023) · cites this paper as Yang et al., 2022
The Results identify alkanesulfonate monooxygenase, encoded by ssuD/ssuE, as responsible for desulfonating 6:2 FTSA; the Discussion also links the ssuEADCB cassette to alkanesulfonate use. But the Conclusion assigns haloacid dehalogenase and cytochrome P450 roles in defluorination, not desulfonation, and the passages found do not identify nitriloacetate monooxygenase as a desulfonating enzyme. No page numbers are available in our copy. (LLM, conf=0.90)
Experimental — accuracy not yet measuredRhodococcus jostii RHA1 desulfonates and defluorinates FTSA.
“Rhodococcus jostii RHA1 for FTSA desulfonation and defluorination (Yang et al., 2022)”
From A review of microbial degradation of per- and polyfluoroalkyl substances (PFAS): Biotransformation routes and enzymes (2023) · cites this paper as Yang et al., 2022
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Cites
Persistence of Perfluoroalkyl Acid Precursors in AFFF-Impacted Groundwater and Soil
Houtz, E. F., Higgins, C. P., Field, J. A., & Sedlak, D. L. (2013) · Environmental Science & Technology · doi:10.1021/es4018877 · Cited by 849 · see citing works
Quantitative determination of fluorotelomer sulfonates in groundwater by LC MS/MS
Schultz, M. M., Barofsky, D. F., & Field, J. A. (2004) · Environmental Science & Technology · doi:10.1021/es035031j · Cited by 373 · see citing works
Wang, N., Liu, J., Buck, R. C., Korzeniowski, S. H., Wolstenholme, B. W., Folsom, P. W., & Sulecki, L. M. (2011) · Chemosphere · doi:10.1016/j.chemosphere.2010.11.003 · Cited by 333 · see citing works
Biodegradation of Polyfluoroalkyl Phosphates as a Source of Perfluorinated Acids to the Environment
Lee, H., D’eon, J., & Mabury, S. A. (2010) · Environmental Science & Technology · doi:10.1021/es9028183 · Cited by 288 · see citing works
Ahrens, L., Felizeter, S., Sturm, R., Xie, Z., & Ebinghaus, R. (2009) · Marine Pollution Bulletin · doi:10.1016/j.marpolbul.2009.04.028 · Cited by 236 · see citing works
Hamid, H., Li, L. Y., & Grace, J. R. (2020) · Environmental Pollution · doi:10.1016/j.envpol.2019.113835 · Cited by 92 · see citing works
Flagged first, then by citations
Research works printed but not linked: 35
- Chan PW, Yakunin AF, Edwards EA, Pai EF, 2011. Mapping the reaction coordinates of enzymatic defluorination. J. Am. Chem. Soc. 133 (19), 7461– 7468. 21510690 PMC3101105
- Chan WY, Wong M, Guthrie J, Savchenko AV, Yakunin AF, Pai EF, Edwards EA, 2010. Sequence- and activity-based screening of microbial genomes for novel dehalogenases. Microb. Biotechnol. 3 (1), 107– 120. 21255311 PMC3815952
- Donnelly C, Murphy CD, 2009. Purification and properties of fluoroacetate dehalogenase from Pseudomonas fluorescens DSM 8341. Biotechnol. Lett. 31 (2), 245– 250. 18807226
- Eggen T, Moeder M, Arukwe A, 2010. Municipal landfill leachates: a significant source for new and emerging pollutants. Sci. Total Environ. 408 (21), 5147– 5157. 20696466
- Hamid H, Li LY, Grace JR, 2020a. Effect of substrate concentrations on aerobic biotransformation of 6:2 fluorotelomer sulfonate (6:2 FTS) in landfill leachate. Chemosphere 261, 128108. 33113640
- Hand S, Wang B, Chu KH, 2015. Biodegradation of 1,4-dioxane: effects of enzyme inducers and trichloroethylene. Sci. Total Environ. 520, 154– 159. 25813968
- Harding-Marjanovic K, Houtz E, Yi S, Field J, Sedlak D, Alvarez-Cohen L, 2015a. Aerobic biotransformation of fluorotelomer thioether amido sulfonate (Lodyne) in AFFF-amended microcosms. Environ. Sci. Technol. 49, 7666– 7674. 26042823
- Ichiyama S, Kurihara T, Kogure Y, Tsunasawa S, Kawasaki H, Esaki N, 2004. Reactivity of asparagine residue at the active site of the D105N mutant of fluoroacetate dehalogenase from Moraxella sp. B. Biochim. Biophys. Acta 1698 (1), 27– 36. 15063312
- Kertesz MA, 2000. Riding the sulfur cycle–metabolism of sulfonates and sulfate esters in gram-negative bacteria. FEMS Microbiol. Rev. 24 (2), 135– 175. 10717312
- Keuning S, Janssen DB, Witholt B, 1985. Purification and characterization of hydrolytic haloalkane dehalogenase from Xanthobacter autotrophicus GJ10. J. Bacteriol. 163 (2), 635– 639. 4019411 PMC219169
- Key BD, Howell RD, Criddle CS, 1998. Defluorination of organofluorine sulfur compounds by Pseudomonas Sp. Strain D2. Environ. Sci. Technol. 32 (15), 2283– 2287.
- Kharasch ED, Thummel KE, 1993. Identification of cytochrome P450 2E1 as the predominant enzyme catalyzing human liver microsomal defluorination of sevoflurane, isoflurane, and methoxyflurane. Anesthesiology 79 (4), 795– 807. 8214760
- Kim MH, Wang N, Chu KH, 2014. 6:2 Fluorotelomer alcohol (6:2 FTOH) biodegradation by multiple microbial species under different physiological conditions. Appl. Microbiol. Biotechnol. 98 (4), 1831– 1840. 23907259
- Kim MH, Wang N, McDonald T, Chu KH, 2012. Biodefluorination and biotransformation of fluorotelomer alcohols by two alkane-degrading Pseudomonas strains. Biotechnol. Bioeng. 109 (12), 3041– 3048. 22614340
- Kulakova AN, Larkin MJ, Kulakov LA, 1997. The Plasmid-located haloalkane dehalogenase gene from Rhodococcus rhodochrous NCIMB 13064. Microbiology 143 (1), 109– 115. 9025284
- Kurihara T, Yamauchi T, Ichiyama S, Takahata H, Esaki N, 2003. Purification, characterization, and gene cloning of a novel fluoroacetate dehalogenase from Burkholderia sp. FA1. J. Mol. Catal. B: Enzym. 23 (2), 347– 355.
- Lee DG, Chu KH, 2013. Effects of growth substrate on triclosan biodegradation potential of oxygenase-expressing bacteria. Chemosphere 93 (9), 1904– 1911. 23890965
- Lewis M, Kim MH, Liu EJ, Wang N, Chu KH, 2016. Biotransformation of 6:2 polyfluoroalkyl phosphates (6:2 PAPs): effects of degradative bacteria and cosubstrates. J. Hazard. Mater. 320, 479– 486. 27585280
- Marek J, Vévodová J, Smatanová IK, Nagata Y, Svensson LA, Newman J, Takagi M, Damborský J, 2000. Crystal structure of the haloalkane dehalogenase from Sphingomonas paucimobilis UT26. Biochemistry 39 (46), 14082– 14086. 11087355
- Masai E, Yamada A, Healy JM, Hatta T, Kimbara K, Fukuda M, Yano K, 1995. Characterization of biphenyl catabolic genes of gram-positive polychlorinated biphenyl degrader Rhodococcus sp. strain RHA1. Appl. Environ. Microbiol. 61 (6), 2079– 2085. 7793929 PMC167480
- McLeod MP, Warren RL, Hsiao WWL, Araki N, Myhre M, Fernandes C, Miyazawa D, Wong W, Lillquist AL, Wang D, Dosanjh M, Hara H, Petrescu A, Morin RD, Yang G, Stott JM, Schein JE, Shin H, Smailus D, Siddiqui AS, Marra MA, Jones SJM, Holt R, Brinkman FSL, Miyauchi K, Fukuda M, Davies JE, Mohn WW, Eltis LD, 2006. The complete genome of Rhodococcus sp. RHA1 provides insights into a catabolic powerhouse. Proc. Natl. Acad. Sci. U.S.A. 103 (42), 15582– 15587. 17030794 PMC1622865
- Murphy CD, 2016. Microbial degradation of fluorinated drugs: biochemical pathways, impacts on the environment and potential applications. Appl. Microbiol. Biotechnol. 100 (6), 2617– 2627. 26830103
- Place BJ, Field JA, 2012. Identification of novel fluorochemicals in aqueous filmforming foams used by the US military. Environ. Sci. Technol. 46 (13), 7120– 7127. 22681548 PMC3390017
- Sallis PJ, Armfield SJ, Bull AT, Hardman DJ, 1990. Isolation and characterization of a haloalkane halidohydrolase from Rhodococcus erythropolis Y2. J. Gen. Microbiol. 136 (1), 115– 120. 2351952
- Shaw DMJ, Munoz G, Bottos EM, Duy SV, Sauve S, Liu J, Van Hamme JD, 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– 698. 30092525
- Smith JM, Harrison K, Colby J, 1990. Purification and characterization of D-2-haloacid dehalogenase from Pseudomonas putida strain AJ1/23. J. Gen. Microbiol. 136 (5), 881– 886. 2380688
- Strynar M, Dagnino S, McMahen R, Liang S, Lindstrom A, Andersen E, McMillan L, Thurman M, Ferrer I, Ball C, 2015. Identification of novel perfluoroalkyl ether carboxylic acids (PFECAs) and sulfonic acids (PFESAs) in natural waters using accurate mass time-of-flight mass spectrometry (TOFMS). Environ. Sci. Technol. 49 (19), 11622– 11630. 26392038
- van der Ploeg J, van Hall G, Janssen DB, 1991. Characterization of the haloacid dehalogenase from Xanthobacter autotrophicus GJ10 and sequencing of the dhlB gene. J. Bacteriol. 173 (24), 7925– 7933. 1744048 PMC212586
- van der Ploeg JR, Eichhorn E, Leisinger T, 2001. Sulfonate-sulfur metabolism and its regulation in Escherichia coli. Arch. Microbiol. 176 (1–2), 1– 8. 11479697
- Van Hamme JD, Bottos EM, Bilbey NJ, Brewer SE, 2013. Genomic and proteomic characterization of Gordonia sp. NB4–1Y in relation to 6: 2 fluorotelomer sulfonate biodegradation. Microbiology 159 (8), 1618– 1628. 23744905
- Wang B, Chu KH, 2017. Cometabolic biodegradation of 1,2,3-trichloropropane by propane-oxidizing bacteria. Chemosphere 168, 1494– 1497. 27939660
- Wang N, Buck RC, Szostek B, Sulecki LM, Wolstenholme BW, 2012. 5:3 polyfluorinated acid aerobic biotransformation in activated sludge via novel “onecarbon removal pathways”. Chemosphere 87 (5), 527– 534. 22264858
- Wang T, Vestergren R, Herzke D, Yu J, Cousins IT, 2016. Levels, isomer profiles, and estimated riverine mass discharges of perfluoroalkyl acids and fluorinated alternatives at the mouths of Chinese rivers. Environ. Sci. Technol. 50 (21), 11584– 11592. 27689437
- Yin T, Tran NH, Huiting C, He Y, Gin KY-H, 2019. Biotransformation of polyfluoroalkyl substances by microbial consortia from constructed wetlands under aerobic and anoxic conditions. Chemosphere 233, 101– 109. 31170581
- Zhang S, Lu X, Wang N, Buck RC, 2016. Biotransformation potential of 6:2 fluorotelomer sulfonate (6:2 FTSA) in aerobic and anaerobic sediment. Chemosphere 154, 224– 230. 27058914
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- Authors
- Yang, S.-H., Shi, Y., Strynar, M., & Chu, K.-H.
- Affiliations
- Texas A&M University (US)
- Environmental Protection Agency (US)
- Corresponding author
- Chu, Kung-Hui
- Venue
- Journal of Hazardous Materials
- Publisher
- Elsevier BV
- Published
- 2022-02
- Volume
- 423
- Issue
- Pt A
- Pages
- 127052
- ISSN
- 0304-3894 (ISSN-L)
- PMC
- PMC8823295
- OpenAlex
- W3198308926
- Cited by
- 128
- References
- 6
- Citations by year
- 2026: 28 · 2025: 44 · 2024: 32 · 2023: 14 · 2022: 10
- FWCI
- 5.30
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Licence
- www.elsevier.com/tdm/userlicense/1.0/ (tdm)
- www.elsevier.com/legal/tdmrep-license (tdm)
- www.elsevier.com/open-access/userlicense/1.0/ (am, 580 d)
- doi.org/10.15223/policy-017 (stm-asf)
- doi.org/10.15223/policy-037 (stm-asf)
- doi.org/10.15223/policy-012 (stm-asf)
- doi.org/10.15223/policy-029 (stm-asf)
- doi.org/10.15223/policy-004 (stm-asf)
- Locations
- Journal of Hazardous Materials (acceptedVersion)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- Funders
- Texas A&M University System
- National Science Foundation (1914707)
- Topics
- Physical Sciences › Environmental Science › Environmental Chemistry › Per- and polyfluoroalkyl substances research
- Physical Sciences › Environmental Science › Pollution › Microbial bioremediation and biosurfactants
- Physical Sciences › Environmental Science › Environmental Chemistry › Environmental Chemistry and Analysis
- Keywords
- Rhodococcus jostii RHA1, desulfonation, defluorination, biotransformation, per- and polyfluoroalkyl substances, alkane monooxygenase, cytochrome P450, haloacid dehalogenase, gene expression, degradation metabolites
- MeSH terms
- Carbon, Fluorocarbons, Rhodococcus, Sulfonic Acids, Sulfur
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