Biosynthesis of fluoroacetate and 4-fluorothreonine by Streptomyces cattleya. Glycine and pyruvate as precursors

(Note: The full text of this document is currently only available in the PDF Version )

John T. G. Hamilton, Muhammad R. Amin, David B. Harper and David O’Hagan


Abstract

Using 19F NMR spectroscopy, 13C-labelled glycines and pyruvates are shown to be incorporated at high levels into fluoroacetate and 4-fluorothreonine by resting cells of Streptomyces cattleya; the labelling patterns illustrate a conversion of glycine via serine to pyruvate, where the C-2 and C-3 carbon atoms of pyruvate contribute both carbon atoms of fluoroacetate and C-3 and C-4 of 4-fluorothreonine respectively.


References

  1. D. B. Harper and D. O'Hagan, Nat. Prod. Rep., 1994, 11, 123 RSC.
  2. J. J. M. Meyer and D. O'Hagan, Chem. Br., 1992, 785 Search PubMed.
  3. D. O'Hagan, R. Perry, J. M. Lock, J. J. M. Meyer, L. Dasaradhi, J. T. G. Hamilton and D. B. Harper, Phytochemistry, 1993, 33, 1043 CrossRef CAS.
  4. M. Sanada, T. Miyano, S. Iwadare, J. M. Williamson, B. H. Arison, J. L. Smith, A. W. Douglas, J. M. Liesch and E. Inamine, J. Antibiot., 1986, 39, 259 CAS.
  5. K. A. Reid, R. D. Bowden and D. B. Harper, in Naturally Produced Organohalogens, ed. A. Grimvall and E. W. B. de Leer, Kluwer Acadamic Publishers, Dordrecht, 1995, pp. 269–279 Search PubMed.
  6. K. A. Reid, J. T. G. Hamilton, R. D. Bowden, D. O'Hagan, L. Dasaradhi, M. R. Amin and D. B. Harper, Microbiol., 1995, 141, 1385 Search PubMed.
  7. S. O. Thomas, V. L. Singleton, J. A. Lowery, R. W. Sharpe, L. M. Preuss, J. N. Porter, J. H. Mowat and N. Bohonos, Antibiotics Ann., 1957, 1956–7, 716 Search PubMed.
  8. G. O. Morton, J. E. Lancaster, G. E. Van Lear, W. Fulmor and W. E. Meyer, J. Am. Chem. Soc., 1969, 91, 1535 CrossRef CAS.
  9. A. R. McGuire, W.-d. Meng, S. M. Roberts and A. J. Willetts, J. Chem. Soc., Perkin Trans. 1, 1993, 1795 RSC.
  10. J. T. G. Hamilton, C. D. Murphy, M. R. Amin, D. O'Hagan and D. B. Harper, unpublished work.
  11. S. M. Klein and R. D. Sagers, J. Bacteriol., 1962, 83, 121 CAS.
  12. T. Tamura, M. Wada, N. Esaki and K. Sato, J. Bacteriol., 1995, 177, 2265 CAS.
  13. J. Nieschalk, J. T. G. Hamilton, C. D. Murphy, D. B. Harper and D. O'Hagan, Chem. Commun., 1997, following paper Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.