Microbial Baeyer-Villiger oxidation of prochiral polysubstituted cyclohexanones by recombinant whole-cells expressing two bacterial monooxygenases

European Journal of Organic Chemistry

Volumn , Issue 5, 2005, Pages 809-816

  Mihovilovic, Marko D ^a   Rudroff, Florian ^a   Grötzl, Birgit ^a   Stanetty, Peter ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Baeyer Villiger oxidation; Biocatalysis; Biotransformations; Ketones; Oxygenases

Indexed keywords

3,5 DIMETHYLCYCLOHEXANONE DERIVATIVE; CYCLOHEXANONE DERIVATIVE; CYCLOHEXANONE MONOOXYGENASE; CYCLOPENTANONE MONOOXYGENASE; LACTONE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ACINETOBACTER; ARTICLE; BACTERIAL CELL; BAEYER VILLIGER REACTION; BIOCATALYST; BIOTRANSFORMATION; CHIRALITY; COMAMONAS; CONFORMATION; ELECTROCHEMICAL ANALYSIS; ENANTIOSELECTIVITY; ENZYME SPECIFICITY; ESCHERICHIA COLI; HYBRIDIZATION; LIPOPHILICITY; NONHUMAN; PROTEIN EXPRESSION; STEREOCHEMISTRY; WHOLE CELL;

EID: 15044351658     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400676     Document Type: Article

References (63)

1. a) G. R. Krow, Org. React. 1993, 43, 251-798;
2. b) M. Renz, B. Meunier, Eur. J. Org. Chem. 1999, 737-750;
3. c) M. D. Mihovilovic, F. Rudroff, B. Grötzl, Curr. Org. Chem. 2004, 8, 1057-1069.
4. C. Bolm, in Peroxide Chemistry (Ed.: W. Adam), Wiley-VCH, Weinheim, 2000, 494-510 and references cited therein.
5. C. T. Walsh, Y.-C. J. Chen, Angew. Chem. 1988, 100, 342-352.
6. S. M. Roberts, P. W. H. Wan, J. Mol. Catal. B: Enzym. 1998, 4, 111-136.
7. M. D. Mihovilovic, B. Müller, P. Stanetty, Eur. J. Org. Chem. 2002, 3711-3730.
8. N. M. Kamerbeek, D. B. Janssen, W. J. H. van Berkel, M. W. Fraaije, Adv. Synth. Catal. 2003, 345, 667-678.
9. N. A. Donoghue, D. B. Norris, P. W. Trudgill, Eur. J. Biochem. 1976, 63, 175-192.
10. J. D. Stewart, Curr. Org. Chem. 1988, 2, 195-216.
11. S. Colonna, N. Gaggero, C. Richelmi, P. Pasta, NATO Sci. Ser. 1 2000, 33, 133-160.
12. G. Chen, M. M. Kayser, M. D. Mihovilovic, M. E. Mrstik, C. A. Martinez, J. D. Stewart, New J. Chem. 1999, 23, 827-832.
13. For another recombinant E. coli overexpression system for CHMO applied in whole-cell biocatalysis see: a) D. S. Doig, M. L. O'Sullivan, S. Patel, J. M. Ward, J. M. Woodley, Enzyme Microb. Technol. 2001, 28, 265-274;
14. b) D. S. Doig, H. Simpson, V. Alphand, R. Furstoss, M. J. Woodley, Enzyme Microb. Technol. 2003, 32, 347-355.
15. J. D. Stewart, K. W. Reed, M. M. Kayser, J. Chem. Soc., Perkin Trans. 1 1996, 755-757.
16. J. D. Stewart, W. R. Kieth, J. Zhu, G. Chen, M. M. Kayser, J. Org. Chem. 1996, 61, 7652-7653.
17. M. M. Kayser, G. Chen, J. D. Stewart, J. Org. Chem. 1998, 63, 7103-7106.
18. S. Rissom, U. Schwarz-Linek, M. Vogel, V. I. Tishkov, U. Kragl, Tetrahedron: Asymmetry 1997, 8, 2523-2526.
19. H. D. Simpson, V. Alphand, R. Furstoss, J. Mol. Catal. B: Enzym. 2001, 16, 101-109.
20. Z. A. Walton, J. D. Stewart, Biotechnol. Prog. 2002, 18, 262-268.
21. N. Berezina, V. Alphand, R. Furstoss, Tetrahedron Asymm. 2002, 13, 1953-1955.
22. S. D. Doig, P. J. Avenell, P. A. Bird, P. Gallati, K. S. Lander, G. J. Lye, R. Wohlgemuth, J. M. Woodley, Biotechnol. Prog. 2002, 18, 1039-1046.
23. V. Alphand, G. Carrea, R. Wohlgemuth, R. Furstoss, J. M. Woodley, Trends Biotechnol. 2003, 21, 318-323.
24. a) M. Griffin, P. W. Trudgill, Eur. J. Biochem. 1976, 63, 199-209;
25. b) P. W. Trudgill, Methods Enzymol. 1990, 88, 77-81.
26. H. Iwaki, Y. Hasegawa, P. C. K. Lau, S. Wang, M. M. Kayser, Appl. Environ. Microbiol. 2002, 68, 5681-5684.
27. H. Sandy, A. J. Willetts, Biotechnol. Lett. 1989, 2, 615-620.
28. M. T. Bes, R. Villa, S. M. Roberts, P. W. H. Wan, A. J. Willetts, J. Mol. Catal. B: Enzym. 1996, 1, 127-134.
29. M. D. Mihovilovic, B. Müller, M. M. Kayser, P. Stanetty, Synlett 2002, 700-702.
30. M. D. Mihovilovic, B. Müller, A. Schulze, P. Stanetty, M. M. Kayser, Eur. J. Org. Chem. 2003, 2243-2249.
31. S. Wang, M. M. Kayser, H. Iwaki, P. C. K. Lau, J. Mol. Catal. B: Enzym. 2003, 211-218.
32. M. D. Mihovilovic, G. Chen, S. Wang, B. Kyte, F. Rochon, M. M. Kayser, J. D. Stewart, J. Org. Chem. 2001, 733-738.
33. M. D. Mihovilovic, B. Müller, M. M. Kayser, J. D. Stewart, P. Stanetty, Synlett 2002, 703-706.
34. M. Taschner, D. J. Black, J. Am. Chem. Soc. 1988, 110, 6892-6893.
35. M. J. Taschner, A. S. Aminbhavi, Tetrahedron Lett. 1989, 30, 1029-1032.
36. F. Yokokawa, Y. Hamada, T. Shioiri, Chem. Commun. 1996, 871-872.
37. D. J. Duchamp, A. R. Branfman, A. C. Button, K. L. Rinehart, J. Am. Chem. Soc. 1973, 95, 4077-4078.
38. a) R. K. Boeckmann, J. E. Starrett, D. G. Nickell, P.-E. Sum, J. Am. Chem. Soc. 1986, 108, 5549-5559;
39. b) C. Neukom, D. P. Richardson, J. H. Myerson, P. A. Bartlett, J. Am. Chem. Soc. 1986, 108, 5559-5568;
40. c) P. DeShong, S. Ramesh, V. Elango, J. Perez, J. Am. Chem. Soc. 1985, 107, 5219-5224;
41. d) R. H. Schlessinger, G. R. Berberwitz, P. Lin, J. Am. Chem. Soc. 1985, 107, 1777-1778;
42. e) S. F. Martin, C. Gluchowski, C. L. Campbell, R. C. Chapman, J. Org. Chem. 1984, 49, 2512-2513;
43. f) F. E. Ziegler, R. T. Wester, Tetrahedron Lett. 1984, 25, 617-620;
44. g) F. E. Ziegler, J. K. Thottathil, Tetrahedron Lett. 1981, 22, 4883-4886;
45. h) R. E. Ireland, P. G. Wuts, B. Ernst, J. Am. Chem. Soc. 1981, 103, 3205-3207.
46. E. Malito, A. Alfieri, M. W. Fraaije, M. Mattevi, Proc. Nat. Acad. Sci. USA 2004, 101, 13157-13162.
47. M. J. Taschner, L. Peddada, P. Cyr, Q. Z. Chen, D. J. Black, NATO ASI Ser., Ser. C1992, 381, 347-360.
48. V. Alphand, R. Furstoss, Tetrahedron: Asymmetry 1992, 3, 379-382.
49. D. R. Kelly, C. J. Knowles, J. G. Mahdi, I. N. Taylor, M. A. Wright, J. Chem. Soc., Chem. Commun. 1995, 729-730.
50. D. R. Kelly, C. J. Knowles, J. G. Mahdi, M. A. Wright, I. N. Taylor, D. E. Hibbs, M. B. Hursthouse, A. K. Mish'al, S. M. Roberts, P. W. H. Wan, G. Grogan, A. J. Willets, J. Chem. Soc., Perkin Trans. 1 1995, 2057-2066.
51. J. D. Stewart, K. W. Reed, C. A. Martinez, J. Zhu, G. Chen, M. M. Kayser, J. Am. Chem. Soc. 1998, 120, 3541-3548.
52. A. Soderquist, J. C. Facelli, W. J. Horton, D. M. Grant, J. Am. Chem. Soc. 1995, 117, 8441-8446.
53. M. Franck-Neumann, M. Miesch, B. Barth, Tetrahedron 1993, 49, 1409-1420.
54. P. Stanetty, M. D. Mihovilovic, K. Mereiter, H. Völlenkle, F. Renz, Tetrahedron 1998, 54, 875-894.
55. R. K. Boeckmann, J. Starrett, Jr., D. G. Nickell, Jr., P.-E. Sum, J. Am. Chem. Soc. 1986, 108, 5549-5559.
56. A. K. Bose, B. Lal, Tetrahedron Lett. 1973, 40, 3937-3940.
57. C. Gennari, C. T. Hewkin, F. Molinari, A. Bernardi, A. Comotti, J. M. Goodman, I. Paterson, J. Org. Chem 1992, 57, 5173-5177.
58. a) O. Repic, S. Vogt, Tetrahedron Lett. 1982, 23, 2729-2732;
59. b) M. S. F. Lie Ken Jie, W. L. K. Lam, J. Chem. Soc., Chem. Commun. 1987, 1460-1461.
60. J. Furukawa, N. Kawabata, J. Nishimura, Tetrahedron Lett. 1966, 3353-3354.
61. Z. Yang, J. C. Lorenz, Y. Shi, Tetrahedron Lett. 1998, 39, 8621-8624.
62. R. Bar, Trends Biotechnol. 1989, 7, 2-4.
63. M. D. Mihovilovic, F. Rudroff, B. Müller, P. Stanetty, Bioorg. Med. Chem. Lett. 2003, 13, 1479-1482.