Directed evolution of the fatty-acid hydroxylase P450 BM-3 into an indole-hydroxylating catalyst

Chemistry - A European Journal

Volumn 6, Issue 9, 2000, Pages 1531-1536

  Li, Qing Shan ^a   Schwaneberg, Ulrich ^a   Fischer, Peter ^a   Schmid, Rolf D ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Bacillus megaterium; Cytochrome P450; Heme proteins; Heterocycles; Oxygenations

Indexed keywords

CYTOCHROME P-450(BM-3); CYTOCHROME P450; CYTOCHROME P450 BM3; CYTOCHROME P450 ISOENZYME; DYE; FATTY ACID; FATTY ACID HYDROXYLASE; INDIRUBIN; INDOLE; INDOLE DERIVATIVE; MUTANT PROTEIN; OXYGENASE; UNCLASSIFIED DRUG;

ARTICLE; BACILLUS MEGATERIUM; CATALYST; CHEMICAL STRUCTURE; CONTROLLED STUDY; DIRECTED MOLECULAR EVOLUTION; ENZYME SPECIFICITY; ENZYMOLOGY; GENETICS; HYDROXYLATION; KINETICS; METABOLISM; NONHUMAN; PROTEIN FAMILY; REACTION ANALYSIS; SITE DIRECTED MUTAGENESIS; STRUCTURE ANALYSIS;

BACILLUS MEGATERIUM; BACTERIAL PROTEINS; CYTOCHROME P-450 ENZYME SYSTEM; FATTY ACIDS; HYDROXYLATION; INDOLES; KINETICS; MIXED FUNCTION OXYGENASES; MUTAGENESIS, SITE-DIRECTED; SUBSTRATE SPECIFICITY;

EID: 0034595354     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000502)6:9<1531::AID-CHEM1531>3.3.CO;2-4     Document Type: Article

References (37)

1. Z. Shao, F. H. Arnold, Curr. Opin. Struct. Biol. 1996, 6, 513-518.
2. J. C. Moore, F. H. Arnold, Nature Biotechnol. 1996, 14, 458-467; F. H. Arnold, A. A. Volkov, Curr. Opin. Chem. Biol. 1999, 3, 54-59.
3. J. C. Moore, F. H. Arnold, Nature Biotechnol. 1996, 14, 458-467; F. H. Arnold, A. A. Volkov, Curr. Opin. Chem. Biol. 1999, 3, 54-59.
4. R. Chen, A. Greer, A. M. Dean, Proc. Natl. Acad. Sci. USA 1996, 93, 12171-12176.
5. C. N. Cronin, J. Biol. Chem. 1998, 27, 24465-24469.
6. L. Hedstrom, L. Szilagyi, W. J. Rutter, Science 1992, 255, 1249-1253.
7. A. F. A. Marsden, B. Wilkinson, J. Cortes, N. J. Dunster, J. Staunton, P. F. Leadlay, Science 1998, 279, 199-202.
8. E. Quemeneur, M. Moutiez, J. B. Charbonnier, A. Menez, Nature 1998, 391, 301-303.
9. C. L. Tucker, J. H. Hurley, T. R. Miller, J. B. Hurley, Proc. Natl. Acad. Sci. USA 1998, 95, 5993-5997.
10. L. Wan, M. B. Twitchett, L. D. Eltis, A. G. Mauk, M. Smith, Proc. Natl. Acad. Sci. USA 1998, 95, 12825-12831.
11. H. M. Wilks, K. W. Hart, R. Feeney, C. R. Dunn, H. Muirhead, W. N. Chia, D. A. Barstow, T. Atkinson, A. R. Clarke, J. J. Holbrook, Science 1988, 242, 1541-1544.
12. T. Yano, S. Oue. H. Kagamiyama, Proc. Natl. Acad. Sci. USA 1998, 95, 5511-5515; S. Oue, A. Okamoto, T. Yano, H. Kagamiyama, J. Biol. Chem. 1999, 274, 2344-2349.
13. T. Yano, S. Oue. H. Kagamiyama, Proc. Natl. Acad. Sci. USA 1998, 95, 5511-5515; S. Oue, A. Okamoto, T. Yano, H. Kagamiyama, J. Biol. Chem. 1999, 274, 2344-2349.
14. J.-H. Zhang, G. Dawes, W. P. C. Stemmer, Proc. Natl. Acad. Sci. USA 1997, 94, 4504-4509.
15. S. S. Boddupalli, R. W. Estabrook, J. A. Peterson, J. Biol. Chem. 1990, 265, 4233-4239.
16. J. H. Capdevila, S. Wie, C. Helvig, J. R. Falck, Y. Belosludtsev, G. Truan, S. E. Graham-Lorence, J. A. Peterson, J. Biol. Chem. 1996, 271, 22663-22671.
17. S. Graham-Lorence, G. Truan, J. A. Peterson, J. R. Flack, S. Wei, C. Helvig, J. H. Capdevilla, J. Biol. Chem. 1997, 272, 1127-1135.
18. H. Li, T. L. Poulos, Nat. Struct. Biol. 1997, 4, 140-146.
19. K. G. Ravichandran, S. Sekhar, S. Boddupalli, C. A. Hasemann, J. A. Peterson, J. Deisenhofer, Science 1993, 261, 731-736.
20. S. Modi, M. J. Sutcliffe, W. U. Primrose, L. Y. Lian, G. C. K. Roberts, Nat. Struct. Biol. 1996, 3, 414-417.
21. C. F. Oliver, S. Modi, W. U. Primrose, L. Y. Lian, G. C. K. Roberts, Biochem. J. 1997, 327, 537-544.
22. Q.-S. Li, U. Schwaneberg, M. Fischer, J. Schmitt, J. Pleiss, R. D. Schmid, unpublished results.
23. C. C. Hyde, E. W. Miles, Biotechnol. 1990, 8, 27-32.
24. D. Murdock, B. D. Ensley, C. Serdar, M. Thalen, Bio/Technol. 1993, 11, 381-385.
25. S. Hart, K. R. Koch, D. R. Woods, J. Gen. Microbiol. 1992, 138, 211-216.
26. E. M. J. Gillam, A. M. A. Aguinaldo, L. M. Notley, G. Kim, R. G. Mundkowski, A. A. Volkov, F. H. Arnold, P. Soucek, J. J. DeVoss, F. P. Guengerich, Biochem. Biophys. Res. Commun. 1999, 265, 469-472.
27. C. F. Oliver, S. Modi, M. J. Sutcliffe, W. U. Primrose, L. Y. Lian, G. C. K. Roberts, Biochemistry 1997, 36, 1567-1572.
28. H. Laatsch, H. Ludwig-Köhn, Liebigs Ann. Chem. 1986, 1847-1853.
29. A. R. Katritzky, W.-Q. Fan, A. E. Koziol, G. J. Palenik, J. Heterocycl. Chem. 1989, 26, 821-828.
30. K. E. O'Connor, A. W. Dobson, S. Hartmans, Appl. Environ. Microbiol. 1997, 63, 4287-4291.
31. R. W. Eaton, P. J. Chapman, J. Bacteriol. 1995, 177, 6983-6988.
32. T. D. Porter, M. J. Coon, J. Biol. Chem. 1991, 266, 13 469-13 472.
33. F. G. Guengerich, J. Biol. Chem. 1991, 266, 10019-10022.
34. U. Schwaneberg, D. Appel, J. Schmitt, R. D. Schmid, Biochem. Biophys. Res. Commun., submitted.
35. J. R. Cherry, M. H. Lamsa, P. Schneider, J. Vind, A. Svendsen, A. Jones, A. H. Pedersen, Nat. Biotechnol. 1999, 17, 379-384.
36. U. Schwaneberg, C. Schmidt-Dannert, J. Schmitt, R. D. Schmid, Anal. Biochem. 1999, 269, 359-366.
37. U. Schwaneberg, A. Sprauer, C. Schmidt-Dannert, R. D. Schmid, J. Chromatogr. A 1999, 848, 149-159.