Microbial Baeyer-Villiger oxidation: Stereopreference and substrate acceptance of cyclohexanone monooxygenase mutants prepared by directed evolution

Organic Letters

Volumn 8, Issue 6, 2006, Pages 1221-1224

  Mihovilovic, Marko D ^a   Rudroff, Florian ^a   Winninger, Alexander ^a   Schneider, Toni ^b   Schulz, Frank ^b   Reetz, Manfred T ^b  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE OXYGENASE; KETONE; OXYGENASE;

ACINETOBACTER; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; ENZYMOLOGY; GENETICS; METABOLISM; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ACINETOBACTER; COMBINATORIAL CHEMISTRY TECHNIQUES; KETONES; MODELS, MOLECULAR; OXIDATION-REDUCTION; OXYGENASES; STEREOISOMERISM;

EID: 33646462587     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0601040     Document Type: Article

References (33)

1. (a) Mihovilovic, M. D.; Müller, B.; Stanetty, P. Eur. J. Org. Chem. 2002, 3711.
2. (b) Kamerbeek, N. M.; Jannsen, D. B.; Berkel, W. J. H.; Fraaije, M. W. Adv. Synth. Catal. 2003, 345, 667.
3. (c) Mihovilovic, M. D.; Rudroff, F.; Grötzl, B. Curr. Org. Chem. 2004, 8, 1057.
4. (d) Flitsch, S.; Grogan, G. In Enzyme Catalysis in Organic Synthesis: A Comprehensive Handbook, 2nd ed.; Drauz, K., Waldmann, H., Eds.; VCH: Weinheim, 2002; Vol. 3, p 1202.
5. (e) Stewart, J. D. Curr. Org. Chem. 1998, 2, 195.
6. (f) Roberts, S. M.; Wan, P. W. H. J. Mol. Catal. B: Enzym. 1998, 4, 111.
7. (g) Willetts, A. Trends Biotechnol. 1997, 15, 55.
8. (h) Walsh, C. T.; Chen, Y.-C. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 333.
9. Mihovilovic, M. D.; Rudroff, F.; Grötzl, B.; Kapitan, P.; Snajdrova, R.; Rydz, J.; Mach, R. Angew. Chem., Int. Ed. 2005, 44, 3609.
10. (a) Mihovilovic, M. D.; Rudroff, F.; Müller, B.; Stanetty, P. Bioorg. Med. Chem. Lett. 2003, 13, 1479.
11. (b) Wang, S.; Kayser, M. M.; Iwaki, H.; Lau, P. C. K. J. Mol. Catal. B: Enzym. 2003, 22, 211.
12. (c) Mihovilovic, M. D.; Müller, B.; Kayser, M. M.; Stanetty, P. Synlett 2002, 700.
13. (a) Mihovilovic, M. D.; Kapitan, P. Tetrahedron Lett. 2004, 45, 2751.
14. (b) Kelly, D. R.; Knowles, C. J.; Mahdi, J. G.; Taylor, I. N.; Wright, M. A. J. Chem. Soc., Chem. Commun. 1995, 729.
15. (c) Alphand, V.; Furstoss, R. J. Org. Chem. 1992, 57, 1306.
16. (a) Svendsen, A. Enzyme Functionality - Design, Engineering, and Screening; Marcel Dekker: New York, 2005.
17. (b) Brakmann, S.; Schwienhorst, A. Evolutionary Methods in Biotechnology (Clever Tricks for Directed Evolution); Wiley-VCH: Weinheim, 2004.
18. (c) Arnold, F. H.; Georgiou, G. Directed Evolution: Screening and Selection Methods; Humana Press: Totowa, NJ, 2003; Vol. 230.
19. Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284.
20. (a) Reetz, M. T. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5716.
21. (b) Reetz, M. T. In Advances in Catalysis; Gates, B. C., Knötzinger, H., Eds.: Elsevier: Amsterdam, 2005; Vol. 49, p 1.
22. Donoghue, N. A.; Norris, D. B.; Trudgill, P. W. Eur. J. Biochem. 1976, 63, 175.
23. Reetz, M. T.; Brunner, B.; Schneider, T.; Schulz, F.; Clouthier, C. M.; Kayser, M. M. Angew. Chem., Int. Ed. 2004, 43, 4075.
24. Fraaije, M. W., Kamerbeek, N. M.; Heidekamp, A. J.; Fortin, R.; Janssen, D. B. J. Biol. Chem. 2004, 279, 3354.
25. Bocola, M.; Schulz, F.; Leca, F.; Vogel, A.; Fraaije, M. W.; Reetz, M. T. Adv. Synth. Catal. 2005, 347, 979.
26. Malito, E.; Alfieri, A.; Fraaije, M. W.; Mattevi, A. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 13157.
27. Mihovilovic, M. D.; Snajdrova, R.; Winninger, A.; Rudroff F. Synlett 2005, 18, 2751.
28. Mihovilovic, M. D.; Müller, B.; Kayser, M. M.; Stewart, J. D.; Stanetty, P. Synlett 2002, 703.
29. Gagnon, R.; Grogan, G.; Groussain, E.; Pedragosa-Moreau, S.; Richardson, P. F.; Roberts, S. M.; Willetts, A. J.; Alphand, V.; Lebreton, J.; Furstoss, R. J. Chem. Soc., Perkin Trans. 1 1995, 2527.
30. Alphand, V.; Mazzini, C.; Lebreton, J.; Furstoss, R. J. Mol. Catal. B: Enzym. 1998, 5, 219.
31. Taschner, M.; Black, D. J. J. Am. Chem. Soc. 1988, 110, 6892.
32. CASTing has recently emerged as an alternative to traditional forms of random mutagenesis: (a) Reetz, M. T.; Bocola, M.; Carballeira, J. D.; Zha, D.; Vogel, A. Angew. Chem., Int. Ed. 2005, 44, 4192.
33. (b) Reetz, M. T.; Wang, L.-W. In part Bocola, M. Angew. Chem., Int. Ed. 2006, 15, 1236.