Biosynthetic short activation of the 2,3,6-trideoxysugar l-rhodinose

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

Jürgen Rohr, Sven-Eric Wohlert, Carsten Oelkers, Andreas Kirschning and Monika Ries


Abstract

The successful incorporation of non-activated [2,3-2H2]-L-rhodinose 4b into landomycin A 7 proves the existence of a short activation pathway for L-rhodinose 4; this result provides evidence of a general saving pathway for deoxy-sugar building blocks and their biosynthetic intermediates, respectively, which become accidentally deactivated during the biosynthetic deoxygenation cascades.


References

  1. A. Kirschning, A. Bechthold and J. Rohr, Top. Curr. Chem., 1997, 188, 1 CAS; J. F. Kennedy and C. A. White, Bioactive Carbohydrates in Chemistry, Biochemistry, and Biology, Ellis Horwood, Chichester, 1983 Search PubMed; S. J. Danishefsky and M. T. Bilodeau, Angew. Chem., 1996, 108, 1483 Search PubMed.
  2. (a) T. Henkel, J. Rohr, J. M. Beale and L. Schwenen, J. Antibiot., 1990, 43, 492 CAS; (b) S. Weber, C. Zolke, J. Rohr and J. M. Beale, J. Org. Chem., 1994, 59, 4211 CrossRef CAS; (c) S.-E. Wohlert, E. Künzel, J. Rohr and J. Frevert, unpublished results; (d) S.-E. Wohlert, Diplomarbeit, Universität Göttingen, 1994; Beninga, Diplomarbeit, Universität Göttingen, 1994; U. Weissbach, Diplomarbeit, Universität Göttingen, 1996.
  3. J. Rohr and R. Thiericke, Nat. Prod. Rep., 1992, 9, 103 RSC; K. Krohn and J. Rohr, Top. Curr. Chem., 1997, 188, 127 CAS.
  4. O. Gabriel, Adv. Chem. Ser., 1973, 117, 387 Search PubMed; H.-w. Liu and J. S. Thorson, Annu. Rev. Microbiol., 1994, 48, 223 CrossRef CAS; J. S. Thorson, S. F. Fo, H.-w. Liu and C. R. Hutchinson, J. Am. Chem. Soc., 1993, 115, 6993 CrossRef CAS; W. Piepersberg, Crit. Rev. Biotechnol., 1994, 14, 251 Search PubMed.
  5. G. Srivastava, O. Hindsgaul and M. M. Palcic, Carbohydr. Res., 1993, 245, 137 CrossRef CAS.
  6. J. G. Bekesi and R. J. Winzler, J. Biol. Chem., 1967, 242, 3873 CAS; M. L. Reitman, I. S. Trowbridge and S. Kornfeld, J. Biol. Chem., 1980, 255, 9900 CAS.
  7. A. Kirschning, U. Hary and M. Ries, Tetrahedron, 1995, 51, 2297 CrossRef CAS.
  8. A. Levy, J. B. Brown and C. J. Lyons, Ind. Eng. Chem., 1960, 52, 211 Search PubMed.
  9. S. K. Goda and M. Akhtar, J. Antibiot., 1992, 45, 984 CAS.
Click here to see how this site uses Cookies. View our privacy policy here.