Evidence for the Combined Participation of a C10 and a C 15 Precursor in the Biosynthesis of Moenocinol, the Lipid Part of the Moenomycin Antibiotics

ChemBioChem

Volumn 4, Issue 11, 2003, Pages 1201-1205

  Neundorf, Ines ^a   Köhler, Christian ^a   Hennig, Lothar ^a   Findeisen, Matthias ^a   Arigoni, Duilio ^b   Welzel, Peter ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b ETH ZURICH   (Switzerland)

Author keywords

Biosynthesis; Isotopic labeling; NMR spectroscopy; Terpenoids

Indexed keywords

ANTIBIOTIC AGENT; BAMBERMYCIN; CARBON; DEUTERIUM; DIMETHYLALLYL DIPHOSPHATE; MOENOCINOL; PYROPHOSPHORIC ACID DERIVATIVE; UNCLASSIFIED DRUG; XYLULOSE;

ARTICLE; BIOSYNTHESIS; NONHUMAN; PRECURSOR; PRIORITY JOURNAL; STREPTOMYCES; STREPTOMYCES GHANAENSIS;

ANTI-BACTERIAL AGENTS; HEMITERPENES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OLIGOSACCHARIDES; ORGANOPHOSPHORUS COMPOUNDS; STREPTOMYCES; TERPENES; XYLULOSE;

STREPTOMYCES; STREPTOMYCES GHANAENSIS;

EID: 0345306653     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/cbic.200300622     Document Type: Article

References (31)

1. a) K. Endler, U. Schuricht, L. Hennig, P. Welzel, U. Holst, W. Aretz, D. Böttger, G. Huber, Tetrahedron Lett. 1998, 39, 13-16;
2. b) U. Schuricht, K. Endler, L. Hennig, M. Findeisen, P. Welzel, J. Prakt. Chem. 2000, 342, 761-767.
3. For a recent review on the nonmevalonate pathway, see: A. Rodríguez-Concepción, A. Boronat, Plant Physiol. 2002, 130, 1079-1089.
4. U. Schuricht, L. Hennig, M. Findeisen, P. Welzel, D. Arigoni, Tetrahedron Lett. 2001, 42, 3835-3837.
5. J. Wouters, Y. Oudjama, S. Ghosh, V. Stalon, L. Droogmans, E. Oldfield, J. Am. Chem. Soc. 2003, 125, 3198-3199, and references cited therein.
6. J.-L. Giner, B. Jaun, D. Arigoni, Chem. Commun. 1998, 1857-1858.
7. L. Charon, J.-F. Hoeffler, C. Pale-Grosdemange, L. M. Lois, A. Boronat, M. Rohmer, Biochem. J. 2000, 346, 737-742.
8. M. Rodríguez-Concepción, N. Campos, L. M. Lois, C. Maldonado, J.-F. Hoeffler, C. Grosdemange-Billiard, M. Rohmer, A. Boronat, FEBS Lett. 2000, 473, 328-332.
9. F. Rohdich, S. Hecht, K. Gärtner, P. Adam, C. Krieger, S. Amslinger, D. Arigoni, A. Bacher, W. Eisenreich, Proc. Natl. Acad. Sci. USA 2002, 99, 1158-1163.
10. B. Altincicek, E. C. Duin, A. Reichenberg, R. Hedderich, A.-K. Kollas, M. Hintz, S. Wagner, J. Wiesner, E. Beck, H. Jomaa, FEBS Lett. 2002, 532, 437-440.
11. F. Rohdich, F. Zepeck, P. Adam, S. Hecht, J. Kaiser, R. Laupitz, T. Gräwert, S. Amslinger, W. Eisenreich, A. Bacher, D. Arigoni, Proc. Natl. Acad. Sci. USA 2003, 100, 1586-1591, and references cited therein.
12. Previously, a different mechanism has been postulated, see L. Charon, C. Pale-Grosdemange, M. Rohmer, Tetrahedron Lett. 1999, 40, 7231-7234.
13. C. Rieder, B. Jaun, D. Arigoni, Helv. Chim. Acta 2000, 83, 2504-2513.
14. J.-F. Hoeffler, A. Hemmerlin, C. Grosdemange-Billiard, T. J. Bach, M. Rohmer, Biochem. J. 2002, 366, 573-583.
15. A. E. Leyes, J. A. Baker, F. M. Hahn, C. D. Poulter, Chem. Commun. 1999, 717-718.
16. A. E. Leyes, J. A. Baker, C. D. Poulter, Org. Lett. 1999, 1, 1071-1073.
17. F. M. Hahn, A. P. Hurlburt, C. D. Poulter, J. Bacteriol. 1999, 181, 4499-4504.
18. D. Arigoni, W. Eisenreich, C. Latzel, S. Sagner, T. Radykewicz, M. H. Zenk, A. Bacher, Proc. Natl. Acad. Sci. USA 1999, 96, 1309-1314.
19. I. Neundorf, dissertation, Universität Leipzig (Germany), 2003.
20. A. Donnerstag, L. Hennig, M. Findeisen, P. Welzel, Magn. Reson. Chem. 1996, 34, 1031-1035.
21. J.-L. Giner, Tetrahedron Lett. 1998, 39, 2479-2482.
22. A breakdown of the freezer for several hours may have contributed to this fact.
23. For a review, see T. J. Simpson, Top. Curr. Chem. 1998, 195, 1-48.
24. J. A. Kennedy, T. Hemscheidt, J. F. Britten, I. D. Spenser, Can. J. Chem. 1995, 73, 1329-1337.
25. For all formulae and HPLC separation, see A. Donnerstag, S. Marzian, D. Müller, P. Welzel, D. Böttger, A. Stärk, H.-W. Fehlhaber, A. Markus, Y. van Heijenoort, J. van Heijenoort, Tetrahedron 1995, 51, 1931-1940.
26. M. Kurz, W. Guba, L. Vértesy, Eur. J. Biochem. 1998, 252, 500-507.
27. A. I. Scott, C. A. Townsend, K. Okada, M. Kajiwara, R. J. Cushley, P. J. Whitman, J. Am. Chem. Soc. 1974, 96, 8069-8080.
28. The other enhanced signals were found at δ = 137.34 (C-14), 141.78 (C-3), 151.06 (C-11) ppm.
29. 11,8.
30. The biosynthesis of anthecotuloide may be related, see J. van Klink, H. Becker, S. Andersson, W. Boland, Org. Biomol. Chem. 2003, 1, 1503-1508.
31. 2H NMR experiment, see S. Braun, H.-O. Kalinowski, S. Berger, 150 and More Basic NMR Experiments, Wiley-VCH, Weinheim, 1998, p. 329.