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Fluorination has been widely used in chemical synthesis, but is rare in nature. The only known biological fluorination scope is represented by the  fl  pathway from  Streptomyces cattleya  that produces fluoroacetate (FAc) and 4-fluorothreonine (4-FT). Here we report the identification of a novel pathway for FAc and 4-FT biosynthesis from the actinomycetoma-causing pathogen  Nocardia brasiliensis  ATCC 700358. The new pathway shares overall conservation with the  fl  pathway in  S. cattleya . Biochemical characterization of the conserved domains revealed a novel fluorinase NobA that can biosynthesize 5’-fluoro-5’-deoxyadenosine (5’-FDA) from inorganic fluoride and  S -adenosyl-l-methionine (SAM). The NobA shows similar halide specificity and characteristics to the fluorination enzyme FlA of the  fl  pathway. Kinetic parameters for fluoride (  K  m   4153 μM,  k  cat   0.073 min  -1 ) and SAM (  K  m   416 μM,  k  cat   0.139 min  -1 ) have been determined, revealing that NobA is slightly (2.3 fold) slower than FlA. Upon sequence comparison, we finally identified a distinct loop region in the fluorinases that probably accounts for the disparity of fluorination activity.

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Characterization of a SAM-dependent fluorinase from a latent biosynthetic pathway for fluoroacetate and 4-fluorothreonine formation in Nocardia brasiliensis