Pseudomonas sp. Strain 273 Metabolizes Decanes with Poly- or Perfluorinated Carbons

During growth with terminally monofluorinated decanes, the soil isolate Pseudomonas 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.