Tritiated chiral alkanes as substrates for soluble methane monooxygenase from Methylococcus capsulatus (Bath): Probes for the mechanism of hydroxylation

Journal of the American Chemical Society

Volumn 119, Issue 8, 1997, Pages 1818-1827

  Valentine, Ann M ^a   Wilkinson, Barrie ^b   Liu, Katherine E ^a   Komar Panicucci, Sonja ^a   Priestley, Nigel D ^b   Williams, Philip G ^c   Morimoto, Hiromi ^c   Floss, Heinz G ^b   Lippard, Stephen J ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF WASHINGTON   (United States)

^c LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TRITIUM; UNSPECIFIC MONOOXYGENASE;

ARTICLE; ENZYME ACTIVITY; ENZYME MECHANISM; HYDROXYLATION; ISOTOPE LABELING; METHYLOCOCCACEAE; REACTION ANALYSIS;

EID: 0030993949     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963971g     Document Type: Article

References (65)

1. Anthony, C. The Biochemistry of Methylotrophs; Academic Press: New York, 1982.
2. Liu, K. E.; Lippard, S. J. In Advances in Inorganic Chemistry; Sykes, A. G., Ed.; Academic Press: San Diego, 1995; Vol. 42, pp 263-289.
3. Lipscomb, J. D. Annu. Rev. Microbiol. 1994, 48, 371-399.
4. Stanley, S. H.; Prior, S. D.; Leak, D. J.; Dalton, H. Biotech. Lett. 1983, 5, 487-492.
5. Nguyen, H.-H. T.; Shiemke, A. K.; Jacobs, S. J.; Hales, B. J.; Lidstrom, M. E.; Chan, S. I. J. Biol. Chem. 1994, 269, 14995-15005.
6. Zahn, J. A.; DiSpirito, A. A. J. Bacteriol. 1996, 178, 1018-1029.
7. Cook, S. A.; Shiemke, A. K. J. Inorg. Biochem. 1996, 63, 273-284.
8. Dalton, H.; Leak, D. J. In Gas Enzymol.; Degn, H., et al., Eds.; D. Reidel Publishing Co.: London, 1985; pp 169-186.
9. Nielsen, A. K.; Gerdes, K.; Degn, H.; Murrell, J. C. Microbiology 1996, 142, 1289-1296.
10. Colby, J.; Dalton, H. Biochem. J. 1978, 171, 461-468.
11. Fox, B. G.; Lipscomb, J. D. Biochem. Biophys. Res. Comm. 1988, 154, 165-170.
12. Fox, B. G.; Froland, W. A.; Dege, J. E.; Lipscomb, J. D. J. Biol. Chem. 1989, 264, 10023-10033.
13. Colby, J.; Dalton, H. Biochem. J. 1979, 177, 903-908.
14. Green, J.; Dalton, H. J. Biol. Chem. 1985, 260, 15795-15801.
15. Liu, K. E.; Valentine, A. M.; Wang, D.; Huynh B. H.; Edmondson, D. E.; Salifoglou, A.; Lippard, S. J. J. Am. Chem. Soc. 1995, 117, 10174-10185.
16. (a) Colby, J.; Stirling, D. I.; Dalton, H. Biochem. J. 1977, 165, 395-402.
17. (b) Green, J.; Dalton, H. J. Biol. Chem. 1989, 264, 17698-17703.
18. Dalton, H. In Advances in Applied Microbiology; Academic Press: 1980; Vol. 26, pp 71-87.
19. Fox, B. G.; Borneman, J. G.; Wackett, L. P.; Lipscomb, J. D. Biochemistry 1990, 29, 6419-6427.
20. Rosenzweig, A. C.; Frederick, C. A.; Lippard, S. J.; Nordlund, P. Nature 1993, 366, 537-543.
21. Rosenzweig, A. C.; Lippard, S. J. Acc. Chem. Res. 1994, 27, 229-236.
22. Woodland, M. P.; Patil, D. S.; Cammack, R.; Dalton, H. Biochim. Biophys. Acta 1986, 873, 237-242.
23. DeWitt, J. G.; Bentsen, J. G.; Rosenzweig, A. C.; Hedman, B.; Green, J.; Pilkington, S.; Papaefthymiou, G. C.; Dalton, H.; Hodgson, K. O.; Lippard, S. J. J. Am. Chem. Soc. 1991, 113, 9219-9235.
24. DeRose, V. J.; Liu, K. E.; Kurtz, D. M., Jr.; Hoffman, B. M.; Lippard, S. J. J. Am. Chem. Soc. 1993, 115, 6440-6441.
25. Liu, K. E.; Lippard, S. J. J. Biol. Chem. 1991, 266, 12836-12839.
26. Feig, A. L.; Lippard, S. J. Chem. Rev. 1994, 94, 759-805.
27. Rosenzweig, A. C.; Nordlund, P.; Takahara, P. M.; Frederick, C. A.; Lippard, S. J. Chem. Biol. 1995, 2, 409-418.
28. Liu, K. E.; Wang, D.; Huynh, B. H.; Edmondson, D. E.; Salifoglou, A.; Lippard, S. J. J. Am. Chem. Soc. 1994, 116, 7465-7466.
29. Liu, K. E.; Valentine, A. M.; Qiu, D.; Edmondson, D. E.; Appelman, E. H.; Spiro, T. G.; Lippard, S. J. J. Am. Chem. Soc. 1995, 117, 4997-4998.
30. Liu, Y.; Nesheim, J. C.; Lee, S.-K.; Lipscomb, J. D. J. Biol. Chem. 1995, 270, 24662-24665.
31. Nesheim, J. C.; Lipscomb, J. D. Biochemistry 1996, 35, 10240-10247.
32. Lee, S.-K.; Nesheim, J. C.; Lipscomb, J. D. J. Biol. Chem. 1993, 268, 21569-21577.
33. Ortiz de Montellano, P. R. In Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1995; pp 245-303.
34. Groves, J. T.; Han, Y.-Z. In Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1995; pp 3-48.
35. Mansuy, D.; Battioni, P. In Activation and Functionalization of Alkanes; Hill, C. L., Ed.; Wiley: New York, 1989; pp 195-218.
36. Guengerich, F. P. In Biological Oxidation Systems, Vol 1; Reddy, C. C., Hamilton, G. A., Madyastha, K. M., Eds.; Academic Press: San Diego, 1990; pp 51-67.
37. Ortiz de Montellano, P. R.; Stearns, R. A. J. Am. Chem. Soc. 1987, 109, 3415-3420.
38. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5699-5707.
39. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687-5698.
40. Newcomb, M.; Le Tadic, M.-H.; Putt, D. A.; Hollenberg, P. F. J. Am. Chem. Soc. 1995, 117, 3312-3313.
41. Newcomb, M.; Le Tadic-Biadatti, M.-H.; Chestney, D. L.; Roberts, E. S.; Hollenberg, P. F. J. Am. Chem. Soc. 1995, 117, 12085-12091.
42. Pratt, J. M.; Ridd, T. I.; King, L. J. J. Chem. Soc., Chem. Commun. 1995, 2297-2298.
43. Bach, R. D.; Mintcheva, I.; Estevéz, C. M.; Schlegel, H. B. J. Am. Chem. Soc. 1995, 117, 10121-10122.
44. Liu, K. E.; Johnson, C. C.; Newcomb, M.; Lippard, S. J. J. Am. Chem. Soc. 1993, 115, 939-947.
45. Choi, S.-Y.; Eaton, P. E.; Hollenberg, P. F.; Liu, K. E.; Lippard, S. J.; Newcomb, M.; Putt, D. A.; Upadhyaya, S. P.; Xiong, Y. J. Am. Chem Soc. 1996, 118, 6547-6555.
46. Ruzicka, F.; Huang, D.-S.; Donnelly, M. I.; Frey, P. A. Biochemistry 1990, 29, 1696-1700.
47. Priestley, N. D.; Floss, H. G.; Froland, W. A.; Lipscomb, J. D.; Williams, P. G.; Morimoto, H. J. Am. Chem. Soc. 1992, 114, 7561-7562.
48. Pacansky, J.; Dupuis, M. J. Am. Chem. Soc. 1982, 104, 415-421.
49. Suter, H. U.; Ha, T.-K. Chem. Phys. 1991, 154, 227-236.
50. Pilkington, S. J.; Dalton, H. In Methods In Enzymology; Academic Press: New York, 1990; Vol. 188, pp 181-190.
51. Fox, B. G.; Froland, W. A.; Jollie, D. R.; Lipscomb, J. D. In Methods In Enzymology; Academic Press: New York, 1990; Vol. 188, pp 191-202.
52. Hultquist, D. E. In Methods in Enzymology; Academic Press: New York, 1978; Vol. 52, pp 463-473.
53. Floss, H. G.; Tsai, M. D. Adv. Enzymol. 1979, 50, 243-302.
54. Andres, H.; Morimoto, H.; Williams, P. G. J. Chem. Soc., Chem. Commun. 1990, 627-628.
55. Priestley, N.; Wilkinson, B.; Floss, H. G. Unpublished results.
56. O'Ferrall, R. A. M. J. Chem. Soc. (B) 1970, 785-790.
57. Ritchie, C. D. In Physical Organic Chemistry: The Fundamental Concepts; Marcel Dekker: New York, 1990; pp 289-307.
58. Froland, W. A.; Wilkinson, B.; Priestley, N. D.; Morimoto, H.; Williams, P. G.; Lipscomb, J. D.; Floss, H. G. Manuscript in preparation.
59. Wilkinson, B.; Zhu, M.; Priestley, N. D.; Nguyen, H.-H. T.; Morimoto, H.; Williams, P. G.; Chan, S. I.; Floss, H. G. J. Am. Chem. Soc. 1996, 118, 921-922.
60. Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628-3634.
61. Groves, J. T.; Viski, P. J. Am. Chem. Soc. 1989, 111, 8537-8538.
62. Groves, J. T.; Stern, M. K. J. Am. Chem. Soc. 1987, 109, 3812-3814.
63. Feig, A. L.; Becker, M.; Schindler, S.; Eldik, R. v.; Lippard, S. J. Inorg. Chem. 1996, 35, 2590-2601.
64. Feig, A. L.; Masschelein, A.; Bakac, A.; Lippard, S. J. J. Am. Chem. Soc. 1997, 119, 334-342.
65. Shestakov, A. F.; Shilov, A. E. J. Mol. Catal. A 1996, 105, 1-7.