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Bacteria covalently incorporate polyfluoroalkyl carboxylates into membrane lipids

Nature Microbiology (2026)Cite this article

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Abstract

Per- and polyfluoroalkyl substances (PFASs), also known as forever chemicals, are global contaminants, but understanding of microbiota–PFAS interactions is limited. Here we show that bacteria covalently incorporate n:3 fluorotelomer carboxylates (FTCAs) into phosphatidylethanolamine and phosphatidylglycerol, two prominent components of bacterial lipid bilayers. Lipidomics of the soil bacterium Pseudomonas sp. strain 273 grown in the presence of 7:3 FTCA or 8:3 FTCA estimated that 7–12% of the bacterium’s glycerophospholipid pool contains the respective polyfluoroacyl chains. This covalent incorporation was observed in five other axenic bacterial cultures tested, including other Pseudomonas species, Escherichia coli and Enterococcus faecalis, albeit with lower incorporation percentages. Incorporation occurred over a broad concentration range, and n:3 FTCAs with varying chain length were covalently incorporated into membranes. Biotransformation of polyfluoroalkyl substances (also known as precursors) results in n:3 FTCA intermediates, which bacteria can covalently incorporate into their glycerophospholipid pools. We conclude that bacteria can form fluoromembranes when exposed to precursors and are a potential PFAS sink.

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Fig. 1: Molecular structure of a representative PE species of Pseudomonas sp. strain 273 grown in the presence of 8:3 FTCA and identification of PE species with 8:3 FTCA replacing one or both FA acyl chains.
Fig. 2: Incorporation of 8:3 FTCA into lipids in strain 273 at varying concentrations.
Fig. 3: Relative abundances of PFASylated PE and PG glycerophospholipid species in different bacterial species grown in the presence of 8:3 FTCA.
Fig. 4: Molecular structure of a representative PE species of Pseudomonas sp. strain 273 with FTCAs with varying carbon chain lengths replacing one FA acyl chain.

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Data availability

All MS proteomics raw data are available at the ProteomeXchange Consortium via the MassIVE database with the unique dataset identifier MSV000098309 (https://doi.org/10.25345/C5SB3XB59). The ProteomeXchange project identifier is PXD065413. The genome of strain 273 is available in GenBank (CP116775) and the JGI IMG system (ID no. 2814122901). The mass spectrometry lipidomic raw data and sequence files are available in the MassIVE database with the unique dataset identifier MSV000100274 (https://doi.org/10.25345/C53T9DM05). The raw MS data for LC–QToF–MS suspect screening analysis are available in the Texas Data Repository (https://doi.org/10.18738/T8/BDF7TU). All other data are available in this Article and its Supplementary Information. Source data are provided with this paper.

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Acknowledgements

This work was supported by the US Department of Defense, Strategic Environmental Research and Development Program (project no. ER23-3601 to G.C., R.L.H. and F.E.L.) and, in part, by ExxonMobil Environmental and Property Solutions Company (to F.E.L.) and the US National Science Foundation Graduate Research Fellowship Program (grant no. DGE 2140745 to J.A.L.).

Author information

Author notes

  1. Yongchao Xie

    Present address: State Key Laboratory of Pollution Control and Resource Reuse, School of Environment, Nanjing University, Nanjing, China

  2. Matthew J. Keller

    Present address: Visiting Scientist Program, Research and Support Unit, Federal Bureau of Investigation Laboratory Division, Quantico, VA, USA

  3. Amanda L. May

    Present address: Center for Renewable Carbon, University of Tennessee Institute for Agriculture, Knoxville, TN, USA

Authors and Affiliations

  1. Department of Civil and Environmental Engineering, University of Tennessee, Knoxville, TN, USA

    Yongchao Xie, Gao Chen, Cynthia M. Swift & Frank E. Löffler

  2. Center for Environmental Biotechnology, University of Tennessee, Knoxville, TN, USA

    Yongchao Xie, Gao Chen, Cynthia M. Swift, Amanda L. May & Frank E. Löffler

  3. Biosciences Division, Oak Ridge National Laboratory, Oak Ridge, TN, USA

    Matthew J. Keller, Dana L. Carper, Paul E. Abraham, Andrew J. Stai, Robert L. Hettich & Jessica A. LaFond

  4. The Bredesen Center for Interdisciplinary Research and Graduate Education, University of Tennessee, Knoxville, TN, USA

    Matthew J. Keller & Andrew J. Stai

  5. Department of Biochemistry and Cellular and Molecular Biology, University of Tennessee, Knoxville, TN, USA

    Broquell M. Wong & Frank E. Löffler

  6. Department of Microbiology, University of Tennessee, Knoxville, TN, USA

    Diana Ramirez

  7. Department of Chemistry, University of Tennessee, Knoxville, TN, USA

    Shawn R. Campagna

  8. Biological Mass Spectrometry Core, University of Tennessee, Knoxville, TN, USA

    Shawn R. Campagna

  9. Department of Civil, Environmental and Construction Engineering, Texas Tech University, Lubbock, TX, USA

    Jessica A. LaFond & Jennifer L. Guelfo

  10. ExxonMobil Environmental and Property Solutions Company, Spring, TX, USA

    Anita Thapalia

  11. ExxonMobil Biomedical Sciences Inc., Spring, TX, USA

    Trent A. Key

  12. Department of Biosystems Engineering and Soil Science, University of Tennessee, Knoxville, TN, USA

    Frank E. Löffler

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Contributions

Y.X. and F.E.L. conceived the study. Y.X., G.C., D.R., C.M.S. and B.M.W. performed the cultivation experiments, enumerated bacteria with qPCR, extracted lipids for lipidomic analysis and prepared samples for proteomic measurements and untargeted LC–MS analysis. M.J.K. and A.J.S. performed mass spectrometry analysis of lipidomic samples. D.L.C. and P.E.A. conducted proteomic analysis. J.A.L. and J.L.G. measured 8:2 FTSA transformation products. Y.X., F.E.L., A.L.M. and S.R.C. performed the initial lipidomic measurements. All authors contributed methodology and supported data analysis and interpretation. Y.X., G.C., R.L.H. and F.E.L. synthesized information. Y.X. and F.E.L. wrote the manuscript. All authors reviewed manuscript drafts and provided input.

Corresponding authors

Correspondence to Yongchao Xie or Frank E. Löffler.

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Extended data

Extended Data Table 1 Comparison of the incorporation percentage determined for different FTCAs at a concentration of 5 µM in cultures of Pseudomonas sp. strain 273
Full size table
Extended Data Table 2 Measurement of 8:2 FTSA biotransformation intermediates (ppb) in Pseudomonas sp. strain 273 cultures grown with 100 µM 8:2 FTSA as the sole sulfur sourcea
Full size table

Extended Data Fig. 1 Schematic illustrating the covalent incorporation of aqueous n:3 FTCAs into the bacterial lipid bilayer and the formation of fluoromembranes.

The fluoromembrane structure displays a fluorinated glycerophospholipid with an n:3 FTCA (n = 5, 7, 8, 9) acyl tail covalently attached to the glycerol backbone at the sn1 position. Free n:3 FTCA and n:3 FTCA that partitions into membranes due to hydrophobic interactions are shown in blue color, while covalently incorporated n:3 FTCA is depicted in red. Note that the covalent incorporation and the non-covalent partitioning of n:3 FTCA into lipid membrane are mechanistically distinct and likely occur simultaneously.

Extended Data Fig. 2 Proposed pathway for covalent incorporation of n:3 FTCAs into membrane glycerophospholipids during de novo lipid biosynthesis.

n:3 FTCAs are activated in a fatty acyl-CoA synthetase (FadD) reaction, and the resulting CoA thioesters are then incorporated into the sn-1 and/or the sn-2 positions of the glycerophospholipid backbone, that is, glycerol-3-phosphate (G3P). These esterification reactions are catalyzed by G3P acyltransferase (PlsB) and/or 1-acyl-sn-G3P acyltransferase(s) (PlsC), forming phosphatidic acids with one or two n:3 FTCA acyl tails. Subsequent headgroup assembly generates complete PFASylated glycerophospholipids, which become part of the lipidome during growth of strain 273 in the presence of a n:3 FTCAs. The heatmaps show enzyme expression changes in Pseudomonas sp. strain 273 cells grown with versus without 8:3 FTCA. Notably, PlsC-1 (2814126759) and PlsC-2 (2814131665) were only detected during growth in the presence of 8:3 FTCA, suggesting higher abundance, particularly of PlsC-2, in the presence of the n:3 FTCA. The asterisks denote significant up-regulation, defined as a Log2 (fold change) > 1 and a p value < 0.05, in the presence of 8:3 FTCA.

Source data

Extended Data Fig. 3 Illustration of precursor subgroups as sources of n:3 FTCAs.

Biotransformation of (from left to right) PAPs58, FTSAms59, FTTAoSs60, FTACs61, FTABs34, FTSs62,63, TBCs62, miscellaneous precursors23, FTIs64, FTSAs32,33,53, FTOHs22, FTALs65,66, and n:2 FTCAs67,68 to n:3 FTCAs has been demonstrated. n:3 FTCAs are subject to incorporation into glycerophospholipids (solid red arrow) or biotransformation to PFCAs68 (solid black arrow). Cell lysis and lipid hydrolysis would release (fluoro)fatty acids, including n:3 FTCAs, the latter available for recycling (that is, renewed covalent incorporation into glycerophospholipids, dashed red arrow) or biotransformation to PFCAs (dashed black arrow).

Extended Data Fig. 4 Molecular structure of PE(7:3FTCA_16:0) detected in the Pseudomonas sp. strain 273 lipidome following growth with 8:2 FTSA as a sulfur source.

The molecular structure (A), tandem mass spectra (B) and associated ion fragments (C) of the target molecule PE(7:3 FTCA_16:0) are shown.The fragmentation pattern of PE(7:3FTCA_16:0) corroborated structure elucidation as seen by [sn1]− at 441 m/z, [sn2]− at 255 m/z, [M-sn1]− at 452 m/z, and a [M-sn2]− at 620 m/z. The fragments with m/z at 357, 337, 317 and 267, correspond to rearranged fragments from the FTCA tail. The mass spectra are normalized to the intensity of the ion fragment with the highest intensity in the selected m/z range.

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Supplementary Table 1. Phosphatidylethanolamine (PE) abundances in different bacteria grown in the presence and in the absence of 8:3 FTCA. Entries 1–12 correspond to different bacterial species grown with and without 8:3 FTCA, whereas entry 13 and entry 14 represent controls where the same concentrations of 8:3 FTCA were added immediately before lipid extraction. Supplementary Table 2. Phosphatidylglycerol (PG) abundances in different bacteria grown in the presence and in the absence of 8:3 FTCA. Entries 1–12 correspond to different bacterial species grown with and without 8:3 FTCA, whereas entry 13 and entry 14 represent controls where the same concentrations of 8:3 FTCA were added immediately before lipid extraction. Supplementary Table 3. Details of the calibrant–internal standard pairs used for the quantification or semi-quantification of 8:2 FTSA transformation products. Supplementary Table 4. Internal standard recoveries for 8:2 FTSA transformation products reported as a relative percentage to the average peak area of the internal standards in the calibration curve.

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Xie, Y., Chen, G., Keller, M.J. et al. Bacteria covalently incorporate polyfluoroalkyl carboxylates into membrane lipids. Nat Microbiol (2026). https://doi.org/10.1038/s41564-026-02301-x

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