Biotransformation of organic sulfides. Predictive active site models for sulfoxidation catalysed by 2,5-diketocamphane 1,2-monooxygenase and 3,6- diketocamphane 1,6-monooxygenase, enantiocomplementary enzymes from Pseudomonas putida NCIMB 10007

Tetrahedron Asymmetry

Volumn 9, Issue 11, 1998, Pages 1899-1916

  Beecher, Jean ^a   Willetts, Andrew ^a  

^a UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

UNSPECIFIC MONOOXYGENASE;

ARTICLE; BACTERIAL GROWTH; BIOTRANSFORMATION; CATALYSIS; ENANTIOMER; ENZYME ACTIVE SITE; ENZYME ACTIVITY; NONHUMAN; PRIORITY JOURNAL; PSEUDOMONAS PUTIDA; STEREOCHEMISTRY;

EID: 0032486163     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00174-8     Document Type: Article

References (39)

1. 1. Willetts, A. Trends in Biotechnology, 1997, 15, 55.
2. 2. Baeyer, A.; Villiger, V. Ber. Dtsch. Chem., 1899, 32, 3625.
3. 3. Latham, J. A.; Walsh, C. J. Am. Chem. Soc., 1987, 109, 3421.
4. 4. Grogan, G. Ph.D Thesis, University of Exeter, 1995.
5. 5. Donaghue, N. A.; Norris, D. B.; Trudgill, P. W. Eur. J. Biochem., 1976, 63, 175.
6. 6. Taschner, M. J.; Chen, Q.-Z. Bioorg. Med. Chem., 1991, 1, 535.
7. 7. Colonna, S.; Gaggero, N.; Casella, L.; Carrea, G.; Pasta, P. Tetrahedron: Asymmetry, 1992, 3, 95.
8. 8. Alphand, V.; Furstoss, R. In Enzyme Cataysis in Organic Synthesis; Drauz, K.; Waldmann, H., Eds.; VCH: 1995, p. 745.
9. 9. Chen, Y.-C.; Peoples, O. P.; Walsh, C. T. J. Bacteriol., 1988, 170, 781.
10. 10. Jones, J. B.; Jakovac, I. J. Can. J. Chem., 1982, 60, 19.
11. 11. Alphand, V.; Furstoss, R. Tetrahedron: Asymmetry, 1992, 3, 379.
12. 12. Carnell, A. J.; Roberts, S. M.; Sik, V.; Willetts, A. J. Chem. Soc., Perkin Trans. 1, 1991, 2385.
13. 13. Taschner, M. J.; Peddada, L.; Cyr, P.; Chen, Q.-Z.; Black, D. J. In Microbial Reagents in Organic Synthesis; Servi, S., Ed.; Kluwer Academic: 1992, p. 347.
14. 14. Ottolina, G.; Pasta, P.; Carrea, G.; Colonna, S.; Dallaville, S.; Holland, H. L. Tetrahedron: Asymmetry, 1995, 6, 1375.
15. 15. Kelly, D. R. Tetrahedron: Asymmetry, 1996, 7, 365.
16. 16. (a) Ottolina, G.; Carrea, G.; Colonna, S.; Ruckemann, A. Tetrahedron: Asymmetry, 1996, 7, 1123.
17. (b) Ottolina, G.; Pasta, P.; Varley, D.; Holland, H. L. Tetrahedron; Asymmetry, 1996, 7, 3427.
18. 17. Kelly, D. R.; Knowles, C. J.; Hadhi, J. G.; Taylor, I. N.; Wright, M. A. Tetrahedron: Asymmetry, 1996, 7, 365.
19. 18. Gagnon, R.; Grogan, G.; Roberts, S. M.; Villa, R.; Willetts, A. J. Chem. Soc., Perkin Trans. 1, 1995, 1505.
20. 19. Horowitz, N. H. Proc. Nat. Acad. Sci., 1945, 31, 153.
21. 20. Hegeman, G. D.; Rosenberg, S. L. Ann. Rev. Microbiol., 1970, 24, 429.
22. 21. Grogan, G.; Roberts, S. M.; Wan, P.; Willetts, A. Biotechnol. Lett., 1993, 15, 913.
23. 22. Grogan, G.; Roberts, S. M.; Willetts, A. J. Chem. Soc., Chem. Commun., 1993, 699.
24. 23. Grogan, G.; Roberts, S. M.; Wan, P.; Willetts, A. Biotechnol. Lett., 1994, 16, 1173.
25. 24. Gagnon, G.; Grogan, G.; Levitt, M. S.; Roberts, S. M.; Wan, P.; Willetts, A. J. Chem. Soc., Perkin Trans. 1, 1995, 2537.
26. 25. Gagnon, R.; Grogan, G.; Groussain, E.; Pedragosa-Moreau, S.; Richardson, P.; Roberts, S. M.; Wan, P.; Willetts, A.; Alphand, V.; Lebreton, J.; Furstoss, R. J. Chem. Soc., Perkin Trans. 1, 1995, 2527.
27. 26. Beecher, J.; Grogan, G.; Roberts, S.; Willetts, A. Biotechnol. Lett., 1996, 18, 571.
28. 27. Beecher, J. Ph.D Thesis, University of Exeter, 1998.
29. 28. Jones, K. H.; Smith, R. T.; Trudgill, P. W. J. Gen. Microbiol., 1993, 139, 797.
30. 29. Holland, H. L. In Organic Synthesis with Oxidative Enzymes; VCH: 1992, p. 255.
31. 30. Branden, C.; Tooze, J. In Introduction to Protein Structure; Garland Publishing: 1991, p. 141.
32. 31. HyperChem from HYPERCUBE INC., Waterloo, Ontario, Canada. Minimisations were done in vacuo using the Polak-Ribiere algorithm, which is a cojugate gradient method: the maximum number of cycles was set for 390 and the RMS gradient default value was 0.1 kcal[A mol].
33. 32. Holland, H. L.; Brown, F. M.; Lakshmaiah, G.; Larsen, B. G.; Patel, M. Tetrahedron: Asymmetry, 1997, 8, 683.
34. 33. Freutel, J.; Chang, Y.-T.; Collins, J.; Loew, G.; Ortiz de Montellano, P. R. J. Am. Chem. Soc., 1994, 116, 11643.
35. 34. Harris, D.; Loew, G. J. Am. Chem. Soc., 1995, 117, 2738.
36. 35. Poulos, T. L.; Finzel, B. C.; Gunsalus, I. C.; Wagner, G. C.; Kraut, J. J. Biol. Chem., 1985, 260, 16122.
37. 36. Walsh, C. T.; Chen, Y.-C. J. Angew. Chem. Int. Ed. Engl., 1988, 27, 333.
38. 37. Deslongchamps, P. In Stereoelectronic Effects in Organic Chemistry; Pergamon: Oxford, 1983, p. 124.
39. 38. Conrad, H. E.; Dubus, R.; Namdtvedt, M. J.; Gunsalus, I. C. J. Biol. Chem., 1965, 240, 495.