Changing the Regioselectivity of a P450 from C15 to C11 Hydroxylation of Progesterone

ChemBioChem

Volumn 13, Issue 8, 2012, Pages 1161-1166

  Nguyen, Kim Thoa ^a   Virus, Cornelia ^a   Günnewich, Nils ^a   Hannemann, Frank ^a   Bernhardt, Rita ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Cytochromes; Directed evolution; Hydroxylation; Mutagenesis; Regioselectivity; Steroids

Indexed keywords

CYP106A2; CYTOCHROME P450; HYDROXYPROGESTERONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ENZYME ACTIVITY; HYDROXYLATION; PRIORITY JOURNAL; SCREENING; SITE DIRECTED MUTAGENESIS;

AMINO ACID SEQUENCE; CYTOCHROME P-450 ENZYME SYSTEM; HYDROXYLATION; MOLECULAR SEQUENCE DATA; PROGESTERONE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84861453937     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201100811     Document Type: Article

References (45)

1. R. Bernhardt, J. Biotechnol. 2006, 124, 128.
2. V. B. Urlacher, S. Eiben, Trends Biotechnol. 2006, 24, 324.
3. F. Hannemann, A. Bichet, K. M. Ewen, R. Bernhardt, Biochim. Biophys. Acta Gen. Subj. 2007, 1770, 330.
4. R. Fasan, M. M. Chen, N. C. Crook, F. H. Arnold, Angew. Chem. 2007, 119, 8566; Angew. Chem. Int. Ed. 2007, 46, 8414;
5. R. Fasan, N. C. Crook, M. W. Peters, P. Meinhold, T. Buelter, M. Landwehr, P. C. Cirino, F. H. Arnold, Biotechnol. Bioeng. 2011, 108, 500;
6. C. J. C. Whitehouse, W. Yang, J. A. Yorke, H. G. Tufton, L. C. I. Ogilvie, S. G. Bell, W. Zhou, M. Bartlam, Z. Rao, L.-L. Wong, Dalton Trans. 2011, 40, 10383-10396;
7. F. E. Zilly, J. P. Acevedo, W. Augustyniak, A. Deege, U. W. Hausig, M. T. Reetz, Angew. Chem. 2011, 123, 2772; Angew. Chem. Int. Ed. 2011, 50, 2720.
8. S. Eiben, H. Bartelmas, V. B. Urlacher, Appl. Microbiol. Biotechnol. 2007, 75, 1055;
9. J. C. Lewis, P. S. Coelho, F. H. Arnold, Chem. Soc. Rev. 2011, 40, 2003;
10. J. Nazor, S. Dannenmann, R. O. Adjei, Y. B. Fordjour, I. T. Ghampson, M. Blanusa, D. Roccatano, U. Schwaneberg, Protein Eng. Des. Sel. 2008, 21, 29;
11. J. Reinen, L. L. Kalma, S. Begheijn, F. Heus, J. N. Commandeur, N. P. Vermeulen, Xenobiotica 2011, 41, 59;
12. C. Ruth, A. Glieder, ChemBioChem 2010, 11, 761.
13. R. L. Lindberg, M. Negishi, Nature 1989, 339, 632.
14. B. Bottner, H. Schrauber, R. Bernhardt, J. Biol. Chem. 1996, 271, 8028.
15. B. Bottner, R. Bernhardt, Endocr. Res. 1996, 22, 455;
16. B. Bottner, K. Denner, R. Bernhardt, Eur. J. Biochem. 1998, 252, 458.
17. S. Kille, F. E. Zilly, J. P. Acevedo, M. T. Reetz, Nat. Chem. 2011, 3, 738.
18. R. Rauschenbach, M. Isernhagen, C. Noeske-Jungblut, W. Boidol, G. Siewert, Mol. Gen. Genet. 1993, 241, 170.
19. A. Berg, M. Ingelman-Sundberg, J. A. Gustafsson, Acta Biol. Med. Ger. 1979, 38, 333;
20. M. Lisurek, M. J. Kang, R. W. Hartmann, R. Bernhardt, Biochem. Biophys. Res. Commun. 2004, 319, 677;
21. M. J. Kang, M. Lisurek, R. Bernhardt, R. W. Hartmann, Rapid Commun. Mass Spectrom. 2004, 18, 2795.
22. H. Morita, M. Zhou, M. F. Foecking, E. P. Gomez-Sanchez, E. N. Cozza, C. E. Gomez-Sanchez, Endocrinology 1996, 137, 2308;
23. G. W. Souness, D. J. Morris, Hypertension 1996, 27, 421.
24. J. Tamm, M. Seckelmann, U. Volkwein, E. Ludwig, Br. J. Dermatol. 1982, 107, 63;
25. A. H. van der Willigen, J. D. Peereboom-Wynia, T. van Joost, E. Stolz, Acta Derm.-Venereol. 1987, 67, 82.
26. C. Barranco, Nat. Rev. Gastroenterol. Hepatol. 2010, 7, 240.
27. A. Yamada, M. Yamada, Y. Fujita, T. Nishigami, K. Nakasho, K. Uematsu, J. Biol. Chem. 2001, 276, 4604.
28. S. Bleif, F. Hannemann, M. Lisurek, J. P. von Kries, J. Zapp, M. Dietzen, I. Antes, R. Bernhardt, ChemBioChem 2011, 12, 576;
29. S. Bleif, F. Hannemann, J. Zapp, D. Hartmann, J. Jauch, R. Bernhardt, Appl. Microbiol. Biotechnol. 2011, 413, 940-951.
30. M. Lisurek, B. Simgen, I. Antes, R. Bernhardt, ChemBioChem 2008, 9, 1439.
31. M. Bureik, M. Lisurek, R. Bernhardt, Biol. Chem. 2002, 383, 1537.
32. C. Virus, R. Bernhardt, Lipids 2008, 43, 1133;
33. C. Virus, PhD thesis, Universität des Saarlandes (Germany), 2006.
34. R. Rauschenbach, PhD thesis, Freie Universität Berlin (Germany), 1993.
35. M. Imai, H. Shimada, Y. Watanabe, Y. Matsushima-Hibiya, R. Makino, H. Koga, T. Horiuchi, Y. Ishimura, Proc. Natl. Acad. Sci. USA 1989, 86, 7823;
36. D. Kim, Y. S. Heo, P. R. Ortiz de Montellano, Arch. Biochem. Biophys. 2008, 474, 150;
37. L. S. Koo, R. A. Tschirret-Guth, W. E. Straub, P. Moenne-Loccoz, T. M. Loehr, P. R. Ortiz de Montellano, J. Biol. Chem. 2000, 275, 14112;
38. R. Raag, S. A. Martinis, S. G. Sligar, T. L. Poulos, Biochemistry 1991, 30, 11420;
39. G. Truan, J. A. Peterson, Arch. Biochem. Biophys. 1998, 349, 53;
40. H. J. Ruijssenaars, E. M. Sperling, P. H. Wiegerinck, F. T. Brands, J. Wery, J. A. de Bont, J. Biotechnol. 2007, 131, 205.
41. F. Hannemann, C. Virus, R. Bernhardt, J. Biotechnol. 2006, 124, 172.
42. A. J. Straathof, S. Panke, A. Schmid, Curr. Opin. Biotechnol. 2002, 13, 548;
43. D. Zehentgruber, F. Hannemann, S. Bleif, R. Bernhardt, S. Lutz, ChemBioChem 2010, 11, 713.
44. B. Simgen, J. Contzen, R. Schwarzer, R. Bernhardt, C. Jung, Biochem. Biophys. Res. Commun. 2000, 269, 737.
45. F. Hannemann, A. K. Bera, B. Fischer, M. Lisurek, K. Teuchner, R. Bernhardt, Biochemistry 2002, 41, 11008.