Mixed acetate-glycerol biosynthesis and formation of benzoate directly from shikimate in Streptomyces sp.

European Journal of Organic Chemistry

Volumn , Issue 23, 2004, Pages 4771-4777

  Hoffmann, Luise ^a   Grond, Stephanie ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Benzoate biosynthesis; Biosynthesis; Lactones; Natural products; Shikimate; Streptomyces

Indexed keywords

ACETIC ACID; BENZOIC ACID; CARBON 13; CARBONYL DERIVATIVE; FURAN DERIVATIVE; GAMMA BUTYROLACTONE DERIVATIVE; GLYCEROL; PHENYLALANINE; PYRANOSIDE; SHIKIMIC ACID;

ARTICLE; BACTERIAL STRAIN; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; ISOTOPE LABELING; METABOLITE; NONHUMAN; STREPTOMYCES; STREPTOMYCES GRISEOVIRIDIS;

EID: 10844240584     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400367     Document Type: Article

References (23)

1. S. Grond, I. Papastavrou, A. Zeeck, Eur. J. Org. Chem. 2002, 3237-3242.
2. C. Milkowski, D. Strack, Phytochemistry 2004, 65, 517-524.
3. J.-F. Hu, D. Wunderlich, I. Sattler, A. Härtl, I. Papastavrou, S. Grond, S. Grabley, X.-Z. Feng, R. Thiericke, J. Antibiot. 2000, 944-953.
4. S. Grond, H.-J. Langer, P. Henne, I. Sattler, R. Thiericke, S. Grabley, H. Zähner, A. Zeeck, Eur. J. Org. Chem. 2000, 929-937.
5. Y. Yamada, "Autoregulatory factors and regulation of antibiotic production", in Streptomyces, in Microbial signalling and communication (Eds.: R. England, G. Hobbs, N. Bainton, D. L. Roberts), Cambridge University Press, Cambridge, 1999, pp. 177-196.
6. B. S. Moore, C. Hertweck, Nat. Prod. Rep. 2002, 19, 70-99.
7. T. Kunigami, K. Shin-Ya, K. Furihata, Y. Hayakawa, H. Seto, J. Antibiot. 1998, 57, 880-882.
8. C. Hertweck, B. S. Moore, Tetrahedron 2000, 56, 9115-9120.
9. [9a] A. M. Hill, B. L. Thompson, Chem. Commun. 2003, 1358-1359.
10. [9b] A. M. Hill, B. L. Thompson, J. P. Harris, R. Segret, Chem. Commun. 2003, 1360-1361.
11. [10a] R. Jansen, B. Kunze, H. Reichenbach, E. Jurkiewicz, G. Hunsmann, G. Höfle, Liebigs Ann. Chem. 1992, 357-359.
12. [10b] R. Jansen, P. Washausen, B. Kunze, H. Reichenbach, G. Höfle, Eur. J. Org. Chem. 1999, 1085-1089.
13. J. Rohr, Angew. Chem. 1997, 109, 2284-2289.
14. F. Nerud, P. Sedmera, Z. Zouchová, V. Musilek, M. Vondrácek, Coll. Czech. Chem. Commun. 1982, 47, 1020-1025.
15. P. J. Parsons, P. Lacrouts, A. D. Buss, J. Chem. Soc., Chem. Commun. 1995, 437-438.
16. N. Shikura, J. Yamamura, T. Nihira, J. Bacteriol. 2002, 184, 5151-5157.
17. W. Clegg, E. Egert, H. Fuhrer, H. H. Peter, H. Uhr, A. Zeeck. J. Antibiot. 1985, 38, 1684-1690.
18. J. Rohr, R. Thiericke, Nat. Prod. Rep. 1992, 9, 103-137.
19. Y. Sekiyama, Y. Fujimoto, K. Hasumi, A. Endo, J. Org. Chem. 2001, 66, 5649-5654.
20. A. I. Scott, C. A. Townsend, K. Okada, J. Am. Chem. Soc. 1974, 96, 8069-8080.
21. H. G. Floss, Nat. Prod. Rep. 1997, 433-452.
22. C.-Z. Wang, U. H. Maier, W. Eisenreich, P. Adam, I. Obersteiner, M. Keil, A. Bacher, M. H. Zenk, Eur. J. Org. Chem. 2001, 1459-1465.
23. H. Cho, L. Heide, H. G. Floss, J. Labelled Compd. Radiopharm. 1992, 31, 589-594.