<i>Pseudomonas</i> sp. Strain 273 Metabolizes Decanes with Poly- or Perfluorinated Carbons

During growth with terminally monofluorinated decanes, the soil isolate <i>Pseudomonas</i> sp. strain 273 releases inorganic fluoride and channels fluorometabolites into glycerophospholipid biosynthesis. We explored the ability of this bacterium to metabolize 1,1-difluorodecane (F2-decane), 1,1,1-trifluorodecane (F3-decane), and 1,1,1,2,2-pentafluorodecane (F5-decane) to assess the impacts of increasing degree of fluorination on organismal metabolism. Growth occurred with all three polyfluorodecane substrates, and inorganic fluoride release was observed in cultures amended with F2-decane and F5-decane but not with F3-decane. Fluorine nuclear magnetic resonance spectroscopy (¹⁹F NMR) detected polyfluorinated C₆ and C₄ short-chain fatty acid catabolites suggesting incomplete β-oxidation during catabolism by strain 273. Gas chromatography-mass spectrometry (GC-MS) analysis corroborated the formation of terminally poly- or perfluorinated short-chain fatty acids. Ultrahigh performance liquid chromatography-high resolution mass spectrometry (UHPLC-HRMS) based global lipidome profiling revealed glycerophospholipids with fluorine substitutions at the sn1/sn2 acyl chains and identified a range of glycerophospholipids that contained between two and ten fluorines depending on the growth substrate. These findings advance our understanding of bacterial transformation of alkanes with poly- and perfluorinated carbons and highlight the formation of short-chain fluorinated fatty acids as catabloc products and fluorophospholipids as anabolic products.