Enantiospecific Synthesis of Analogues of the Diketide Intermediate of the Erythromycin Polyketide Synthase (PKS)

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

Rebecca C. Harris, Annabel L. Cutter, Kira J. Weissman, Ulf Hanefeld, Ma′ire C. Timoney and James Staunton


Abstract

The four stereoisomers of 3-hydroxy-2-methylpentanoic acid (1ad) and the structurally modified acids 1ej have been synthesised enantiospecifically and converted into p-nitrophenyl ester and thioester derivatives; as the activated derivatives; they are available for investigations into the substrate selectivity of polyketide synthase (PKS) domains.


References

  1. R. Pieper, C. Kao, C. Khosla, G. Luo and D. E. Cane, Chem. Soc. Rev., 1996, 25, 297 RSC; J. Staunton, P. Caffrey, J. F. Aparicio, G. A. Roberts, S. S. Bethell and P. F. Leadlay, Nat. Struct. Biol., 1996, 3, 188 CrossRef CAS.
  2. K. J. Weissman, C. J. Smith, R. Aggarwal, U. Hanefeld, J. Staunton and P. F. Leadlay, Angew. Chem., Int. Ed. Engl., in the press Search PubMed.
  3. J. R. Gage and D. A. Evans, Org. Synth., 1990, 68, 83.
  4. D. E. Cane, P. C. Prabhakaran, W. Tan and W. R. Ott, Tetrahedron Lett., 1991, 32, 5457 CrossRef CAS.
  5. M. A. Walker and C. H. Heathcock, J. Org. Chem., 1991, 56, 5747 CrossRef CAS.
  6. B. C. Raimundo and C. H. Heathcock, Synlett, 1995, 12, 1213.
  7. I. H. Gilbert, M. Ginty, J. A. O'Neill, T. J. Simpson, J. Staunton and C. L. Willis, Bioorg. Med. Chem. Lett., 1995, 5, 1587 CrossRef CAS.
  8. R. Aggarwal, P. Caffrey, P. F. Leadlay, C. J. Smith and J. Staunton, J. Chem. Soc., Chem. Commun., 1995, 1519 RSC.
  9. B. Neises and W. Steglich, Angew. Chem., Int. Ed. Engl., 1978, 17, 522 CrossRef.
Click here to see how this site uses Cookies. View our privacy policy here.