Sequential asymmetric polyketide heterocyclization catalyzed by a single cytochrome p450 monooxygenase (AurH)

Angewandte Chemie - International Edition

Volumn 47, Issue 46, 2008, Pages 8872-8875

  Richter, Martin E A ^a   Traitcheva, Nelly ^a   Knüpfer, Uwe ^a   Hertweck, Christian ^a,b  

^a HANS KNÖLL INSTITUTE   (Germany)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Authreonin; Heterocycles; Natural products; Oxygenases; Polyketides

Indexed keywords

CHEMICAL BONDS; CHEMICAL REACTIONS; OXYGENATION;

AUTHREONIN; HETEROCYCLES; NATURAL PRODUCTS; OXYGENASES; POLYKETIDES;

POLYMERS;

CYTOCHROME P450; MACROLIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; MASS SPECTROMETRY; METABOLISM; STEREOISOMERISM;

CATALYSIS; CYCLIZATION; CYTOCHROME P-450 ENZYME SYSTEM; MACROLIDES; MASS SPECTROMETRY; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 57349119450     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803714     Document Type: Article

References (33)

1. D. O'Hagan, The Polyketide Metabolites, Ellis Horwood, Chichester, 1991.
2. H. B. Bode, A. Zeeck, J. Chem. Soc. Perkin Trans. 1 2000, 2665-2670.
3. A. J. Woo, W. R. Strohl, N. D. Priestley, Antimicrob. Agents Chemother. 1999, 43, 1662-1668.
4. T. Weber, K. J. Laiple, E. K. Pross, A. Textor, S. Grond, K. Welzel, S. Pelzer, A. Vente, W. Wohlleben, Chem. Biol. 2008, 15, 175-188.
5. M. Oliynyk, C. B. Stark, A. Bhatt, M. A. Jones, Z. A. Hughes-Thomas, C. Wilkinson, Z. Oliynyk, Y. Demydchuk, J. Staunton, P. F. Leadlay, Mol. Microbiol. 2003, 49, 1179-1190.
6. B. M. Harvey, T. Mironenko, Y. Sun, H. Hong, Z. Deng, P. F. Leadlay, K. J. Weissman, S. F. Haydock, Chem. Biol. 2007, 14, 703-714.
7. Y. Sun, X. Zhou, H. Dong, G. Tu, M. Wang, B. Wang, Z. Deng, Chem. Biol. 2003, 10, 431-441.
8. Y. Demydchuk, Y. Sun, H. Hong, J. Staunton, J. B. Spencer, P. F. Leadlay, ChemBioChem 2008, 9, 1136-1145.
9. A. Bhatt, C. B. W. Stark, B. M. Harvey, A. R. Gallimore, Y. A. Demydchuk, J. B. Spencer, J. Staunton, P. F. Leadlay, Angew. Chem. 2005, 117, 7237-7240;
10. Angew. Chem. Int. Ed. 2005, 44, 7075-7078.
11. A. R. Gallimore, C. B. Stark, A. Bhatt, B. M. Harvey, Y. Demydchuck, V. Bolanos-Garcia, D. J. Fowler, J. Staunton, P. F. Leadlay, J. B. Spencer, Chem. Biol. 2006, 13, 453-460.
12. A. R. Gallimore, J. B. Spencer, Angew. Chem. 2006, 118, 4514-4521;
13. Angew. Chem. Int. Ed. 2006, 45, 4406-4413.
14. K. M. Henry, C. A. Townsend, J. Am. Chem. Soc. 2005, 127, 3724-3733.
15. J. He, C. Hertweck, J. Am. Chem. Soc. 2004, 126, 3694-3695.
16. J. He, C. Hertweck, Chem. Biol. 2003, 10, 1225-1232.
17. J. He, C. Hertweck, ChemBioChem 2005, 6, 908-912.
18. N. Traitcheva, H. Jenke-Kodama, J. He, E. Dittmann, C. Hertweck, ChemBioChem 2007, 8, 1841-1849.
19. M. MKller, J. He, C. Hertweck, ChemBioChem 2006, 7, 37-39.
20. J. He, M. MKller, C. Hertweck, J. Am. Chem. Soc. 2004, 126, 16742-16743.
21. R. Winkler, M. Richter, U. Knüpfer, D. Merten, C. Hertweck, Angew. Chem. 2006, 118, 8184-8186;
22. Angew. Chem. Int. Ed. 2006, 45, 8016-8018.
23. Z. Xu, A. Magyar, C. Hertweck, J. Am. Chem. Soc. 2007, 129, 6022-6030.
24. Y. Ishibashi, S. Ohba, S. Nishiyama, S. Yamamura, Bull. Chem. Soc. Jpn. 1995, 68, 3643-3649.
25. I. Ohtani, T. Kusumi, Y. Kashman, H. Kakisawa, J. Am. Chem. Soc. 1991, 113, 4092-4096.
26. Y. Ishibashi, S. Ohaba, S. Nishiyama, S. Yamamura, Bull. Chem. Soc. Jpn. 1995, 68, 3643-3649.
27. E. M. Isin, F. P. Guengerich, Biochim. Biophys. Acta Gen. Subj. 2007, 1770, 314-329.
28. D. Werck-Reichhart, R. Feyereisen, Genome Biol. 2000, 1, 3003.
29. L. L. Wong, Curr. Opin. Chem. Biol. 1998, 2, 263-268.
30. M. C. Rojas, P. Hedden, P. Gaskin, B. Tudzynski, Proc. Natl. Acad. Sci. USA 2001, 98, 5838-5843.
31. W. Nam, Acc. Chem. Res. 2007, 40, 522-531.
32. M. Newcomb, P. F. Hollenberg, M. J. Coon, Arch. Biochem. Biophys. 2003, 409, 72-79.
33. T. Hashimoto, J. Matsuda, Y. Yamada, FEBS Lett. 1993, 329, 35-39.