The biosynthesis of pramanicin: origin of the carbon skeleton

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Paul H. M. Harrison, Donald W. Hughes and R. William Riddoch


Abstract

Incorporation of labelled acetates and serine into pramanicin 1 in Stagonospora sp. ATCC 74235 shows that the carbon skeleton of 1 is derived from eight acetate units and a serine residue, implying that the biosynthesis of 1 proceeds via an acyl–tetramic acid intermediate 3.


References

  1. R. E. Schwartz, G. L. Helms, E. A. Bolessa, K. E. Wilson, R. A. Giacobbe, J. S. Tkacz, G. F. Bills, J. M. Liesch, D. L. Zink, J. E. Curotto, B. Pramanik and J. C. Onishi, Tetrahedron, 1994, 50, 1675 CrossRef CAS.
  2. C. Cow and P. Harrison, Can. J. Chem., 1997, 75, 884 CAS.
  3. For recent reviews, see: C. W. Carreras, R. Pieper and C. Khosla, Top. Curr. Chem., 1997, 188, 85 Search PubMed; D. O'Hagan, Nat. Prod. Rep., 1995, 12, 1 CAS.
  4. S. Shibata, U. Sankawa, H. Taguchi and K. Yamasaki, Chem. Pharm. Bull., 1966, 14, 474 CAS.
  5. C. W. Holzapfel and D. C. Wilkins, Phytochemistry, 1971, 10, 351 CrossRef CAS; R. M. McGrath, P. S. Steyn and N. P. Ferreira, J. Chem. Soc., Chem. Commun., 1973, 812 RSC; R. M. McGrath, P. S. Steyn, N. P. Ferreira and D. C. Neethling, Bioorg. Chem., 1976, 4, 11 CrossRef; A. E. de Jesus, P. S. Steyn, R. Vleggaar, G. W. Kirby, M. J. Varley and N. P. Ferreira, J. Chem. Soc., Perkin Trans. 1, 1981, 3292 RSC; A. A. Chalmers, C. P. Gorst-Allman and P. S. Steyn, J. Chem. Soc., Chem. Commun., 1982, 1367 RSC.
  6. S. Gatenbeck and J. Sierankiewicz, Acta Chem. Scand., 1973, 27, 1825 CAS.
  7. D. Schipper, J. L. van der Baan and F. Bickelhaupt, J. Chem. Soc., Perkin Trans. 1, 1979, 2017 RSC; D. Schipper, J. L. van der Baan, N. Harms and F. Bickelhaupt, Tetrahedron Lett., 1982, 23, 1293 CrossRef CAS.
  8. K. L. Rinehart, Jr., D. D. Weller and C. J. Pearce, J. Nat. Prod., 1980, 43, 1 CrossRef; C. J. Pearce, S. E. Ulrich and K. L. Rinehart, Jr., J. Am. Chem. Soc., 1980, 102, 2510 CrossRef CAS; C. J. Pearce and K. L. Rinehart, Jr., J. Antibiot., 1983, 36, 1536 CAS.
  9. H. Seto, H. Yonehara, S. Aizawa, H. Akutsu, J. Clardy, E. Arnold, M. Tanabe and S. Urano, Koen Yoshishu - Tennen Yuki Kagobutsu Toronkai, Kyushu University, 22nd Conference, 1979, 394(Chem. Abstr., 1980,92, 211459) Search PubMed.
  10. A. Probst and C. Tamm, Helv. Chim. Acta, 1981, 64, 2065 CrossRef CAS.
  11. S. Sakuda, M. Ono, K. Furihata, J. Nakayama, A. Suzuki and A. Isogai, J. Am. Chem. Soc., 1996, 118, 7855 CrossRef CAS.
  12. A. G. McInnes, D. G. Smith, J. A. Walter, L. C. Vining and J. L. C. Wright, J. Chem. Soc., Chem. Commun., 1974, 282 RSC; E. Leete, N. Kowanko, R. A. Newmark, L. C. Vining, A. G. McInnes and J. L. C. Wright, Tetrahedron Lett., 1975, 47, 4103 CrossRef; J. L. C. Wright, L. C. Vining, A. G. McInnes, D. G. Smith and J. A. Walter, Can. J. Biochem., 1977, 55, 678 CAS.
  13. M. Tanabe and S. Urano, Tetrahedron, 1983, 39, 3569 CrossRef CAS.
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