Investigation of glycerol incorporation into soraphen A

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

Alison M. Hill, Jonathan P. Harris and Alexandros P. Siskos


Abstract

Glycerol has been incorporated mid-chain into the polyketide soraphen A 1 at C-3,4 and C-11,12; the pro-(S)-hydroxymethyl group of glycerol is lost and one of the hydrogens in the pro-(R)-hydroxymethyl group is retained at C-11 which excludes hydroxymalonate as the immediate precursor to the vicinal methoxy groups at C-11,12.


References

  1. D. O'Hagan, The Polyketide Metabolites, 1991, Ellis Horwood, Chichester Search PubMed.
  2. A. M. Hill and J. P. Harris, unpublished results.
  3. N. Bedorf, B. Böhlendorf, D. Schomberg, K. Gerth, H. Reichenbach and G. Höfle, unpublished results.
  4. S. Omura, K. Tsuzuki, A. Nakagawa and G. Lukacs, J. Antibiot., 1983, 36, 611 CAS.
  5. K. U. Bindseil and A. Zeeck, Helv. Chim. Acta, 1993, 76, 150 CrossRef CAS.
  6. A. Haber, R. D. Johnson and K. L. Rinehart Jr, J. Am Chem. Soc., 1977, 99, 3541 CrossRef CAS.
  7. S. J. Kakavas, L. Katz and D. Stassi, J. Bacteriol., 1997, 179, 7515 CAS.
  8. J. Nieschalk, J. T. G. Hamilton, C. D. Murphy, D. B. Harper and D. O'Hagan, Chem. Commun., 1997, 799 RSC.
  9. H. Oikawa, K. Yagi, K. Watanabe, M. Honma and A. Ichihara, Chem. Commun., 1997, 97 RSC.
  10. R. E. Hill, A. Iwanow, B. G. Sayer, W. Wysocka and I. D. Spenser, J. Biol. Chem., 1987, 262, 7463 CAS.
  11. S. Jaoua, S. Neff and T. Schupp, Plasmid, 1992, 28, 157 CrossRef CAS.
  12. T. Schupp, C. Toupet, B. Cluzel, S. Neff, S. Hill, J. J. Beck and J. M. Ligon, J. Bacteriol., 1995, 177, 3673 CAS.
Click here to see how this site uses Cookies. View our privacy policy here.