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  • Brief Communication
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Biochemistry

Biosynthesis of an organofluorine molecule

A fluorinase enzyme has been discovered that catalyses carbon–fluorine bond formation.

Abstract

Although fluorine in the form of fluoride minerals is the most abundant halogen in the Earth's crust, only 12 naturally occurring organofluorine compounds have so far been found1, and how these are biosynthesized remains a mystery2. Here we describe an enzymatic reaction that occurs in the bacterium Streptomyces cattleya and which catalyses the conversion of fluoride ion and S-adenosylmethionine (SAM) to 5′-fluoro-5′-deoxyfluoroadenosine (5′-FDA). To our knowledge, this is the first fluorinase enzyme to be identified, a discovery that opens up a new biotechnological opportunity for the preparation of organofluorine compounds.

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Figure 1: The fluorinase enzyme from Streptomyces cattleya mediates the conversion of S-adenosyl-l-methionine (SAM) to 5′-fluoro-5′-deoxyadenosine (5′-FDA).

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References

  1. O'Hagan, D. & Harper, D. B. Nat. Prod. Rep. 11, 123–133 (1994).

    Article  Google Scholar 

  2. O'Hagan, D. & Harper, D. B. in Asymmetric Fluoro-organic Chemistry (ed. Ramachandran, P. V.) 210–225 (Am. Chem. Soc. Symp. Ser. 746, Washington DC, 1999).

  3. Gribble, G. W. Chem. Soc. Rev. 28, 335–346 (1999).

    Article  CAS  Google Scholar 

  4. Hall, R. J. New Phytol. 71, 855–871 (1972).

    Article  CAS  Google Scholar 

  5. Peters, R. A. & Shorthouse, M. A. Nature 216, 80–81 (1967).

    Article  ADS  CAS  Google Scholar 

  6. Sanada, M. et al. J. Antibiot. 39, 259–265 (1986).

    Article  CAS  Google Scholar 

  7. Moss, S. J. Chem. Commun. 2281–2282 (2000).

  8. Murphy, C. D., Moss, J. S. & O'Hagan, D. Appl. Environ. Microbiol. 67, 4919–4921 (2001).

    Article  CAS  Google Scholar 

  9. Gani, D. & Johnson, A. W. J. Chem. Soc. Perkin Trans. 1, 1197–1204 (1982).

    Article  Google Scholar 

Download references

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Correspondence to David O'Hagan.

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The authors declare no competing financial interests.

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O'Hagan, D., Schaffrath, C., Cobb, S. et al. Biosynthesis of an organofluorine molecule. Nature 416, 279 (2002). https://doi.org/10.1038/416279a

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