Regiochemical variations in reactions of methylcubane with tert-butoxyl radical, cytochrome P-450 enzymes, and a methane monooxygenase system

Journal of the American Chemical Society

Volumn 118, Issue 28, 1996, Pages 6547-6555

  Choi, Seung Yong ^a   Eaton, Philip E ^b   Hollenberg, Paul F ^c,d   Liu, Katherine E ^e   Lippard, Stephen J ^e   Newcomb, Martin ^a   Putt, David A ^c   Upadhyaya, Subhash P ^b   Xiong, Yusheng ^b  

^a WAYNE STATE UNIVERSITY   (United States)

^b UNIVERSITY OF CHICAGO   (United States)

^c WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

^e MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHARACTERIZATION; CHEMICAL REACTIONS; ENZYMES; OXIDATION; PHYSICAL CHEMISTRY;

BUTOXY RADICALS; CYTOCHROME ENZYMES; METHANE MONOOXYGENASES; METHYLCUBANE; REGIOCHEMISTRY;

HYDROCARBONS;

CYTOCHROME P450; POLYCYCLIC HYDROCARBON; UNSPECIFIC MONOOXYGENASE;

ANIMAL TISSUE; ARTICLE; ENZYME ACTIVITY; IN VITRO STUDY; NONHUMAN; OXIDATION; RAT; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 8944253773     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952226l     Document Type: Article

References (77)

1. McMillen, D. F.; Golden, D. M. Ann. Rev. Phys. Chem. 1982, 33, 493-532.
2. Cytochrome P-450 Structure, Mechanism and Biochemistry 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum: New York, 1995.
3. Lippard, S. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 344-361.
4. Vincent, J. B.; Olivier-Lilley, G. L.; Averill, B. A. Chem. Rev. 1990, 90, 1447-1467.
5. Feig, A. L.; Lippard, S. J. Chem. Rev. 1994, 94, 759-805.
6. Rosenzweig, A. C; Frederick, C. A.; Lippard, S. J.; Nordlund, P. Nature 1993, 366, 537-543.
7. Rosenzweig, A. C.; Lippard, S. J. Acc. Chem. Res. 1994, 27, 229-236.
8. Rosenzweig, A. C.; Nordlund, P.; Takahara, P. M.; Frederick, C. A.; Lippard, S. J. Chem. & Biol. 1995, 2, 409-418, 632.
9. McMurry, T. J.; Groves, J. T. In Cytochrome P-450 Structure, Mechanism and Biochemistry; Ortiz de Montellano, P. R., Ed.; Plenum: New York, 1986; pp 1-28.
10. Ortiz de Montellano, P. R. In Cytochrome P-450 Structure, Mechanism and Biochemistry; Ortiz de Montellano, P. R., Ed.; Plenum: New York, 1986; pp 217-271.
11. Guengerich, F. P.; Macdonald, T. L. FASEB J. 1990, 4, 2453-2459.
12. Woggon, W.-D.; Fretz, H. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1992; Vol. 2; pp 111-147.
13. Newcomb, M.; La Tadic, M.-H.; Chestney, D. L.; Roberts, E. S.; Hollenberg, P. F. J. Am. Chem. Soc. 1995, 117, 12085-12091.
14. Green, J.; Dalton, H. J. Biol. Chem. 1989, 30, 17698-17703.
15. Ruzicka, F.; Huang, D.-S.; Donnelly, M. I.; Frey, P. A. Biochemistry 1990, 29, 1696-1700.
16. Fox, B. G.; Borneman, J. G.; Wackett, L. P.; Lipscomb, J. D. Biochemistry 1990, 29, 6419-6427.
17. Rataj, M. J.; Kauth, J. E.; Donnelly, M. I. J. Biol. Chem. 1991, 226, 18684-18690.
18. Deighton, N.; Podmore, I. D.; Symons, M. C. R.; Wilkins, P. C.; Dalton, H. J. Chem. Soc., Chem. Commun. 1991, 1086-1088.
19. Dalton, H.; Wilkins, P. C.; Deighton, N.; Podmore, I. D.; Symons, M. C. R. Faraday Discuss. 1992, 93, 163-171.
20. Fu, H.; Newcomb, M.; Wong, C-H. J. Am. Chem. Soc. 1991, 113, 5878-5880.
21. Liu, K. E.; Johnson, C. C.; Newcomb, M.; Lippard. S. J. J. Am. Chem. Soc. 1993, 115, 939-947.
22. 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.
23. Wilkinson, B.; Liu, K. E.; Valentine, A. M.; Komar-Panacucci, S.; Morimoto, H.; Williams, P. G.; Lippard, S. J.; Floss, H. G. Unpublished results.
24. 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.
25. Jones, J. P.; Korzekwa, K. R.; Rettie, A. E.; Trager, W. F. J. Am. Chem. Soc. 1986, 108, 7074-7078.
26. Hanzlik, R. P.; Ling, K.-H. J. Org. Chem. 1990, 55, 3992-3997.
27. Hanzlik, R. P.; Ling, K. H. J. J. Am. Chem. Soc. 1993, 115, 9363-9370.
28. Atkinson, J. K.; Hollenberg, P. F.; Ingold, K. U.; Johnson, C. C.; Le Tadic, M.-H.; Newcomb, M.; Putt, D. A. Biochemistry 1994, 33, 10630-10637.
29. 26
30. Walling, C. Pure Appl. Chem. 1967, 15, 69-80.
31. Schubert, W.; Yoshimine, M.; Pacansky, J. J. Phys. Chem. 1981, 85, 1340-1342.
32. Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1990, 112, 3227-3228.
33. Staneke, P. O.; Ingemann, S.; Eaton, P. E.; Nibbering, N. M. M.; Kass, S. R. J. Am. Chem. Soc. 1994, 116, 6445-6446.
34. Delia, E. W.; Head, N. J.; Mallon, P.; Walton, J. C. J. Am. Chem. Soc. 1992, 114, 10730-10738.
35. Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1994, 116, 6459-6460.
36. Delia, E. W.; Pigou, P. E. J. Am. Chem. Soc. 1984, 106, 1085-1092.
37. Yip, Y. C. Ph.D. Thesis, The University of Chicago, 1993.
38. Eaton, P. E.; Li, J.; Upadhyaya, S. P. J. Org. Chem. 1995, 60, 966-968.
39. Reduction of cubylcarbinyl bromide with lithium triethylborohydride also was successful: Eaton, P. E.; Upadhyaya, S. P. Unpublished results.
40. Chapman, N. B.; Key, J. M.; Toyne, K. J. J. Org. Chem. 1970, 35, 3860-3867.
41. Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1972, 28, 4131-4138.
42. Edward, J. T.; Farrell, P. G.; Langford, G. F. J. Am. Chem. Soc. 1976, 98, 3075-3085.
43. Griffiths, P. G.; Moad, G.; Rizzardo, E.; Solomon, D. H. Aust. J. Chem. 1983, 36, 397-401.
44. Newcomb, M. Tetrahedron 1993, 49, 1151-1176.
45. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901-3924.
46. Barton, D. H. R.; Beviere, S. D.; Chavasiri, W.; Doller, D.; Liu, W. G.; Reibenspies, J. H. New J. Chem. 1992, 16, 1019-1029.
47. Barton, D. H. R.; Chavasiri, W.; Hill, D. R.; Hu, B. New J. Chem. 1994, 18, 611-620.
48. 50 and we believe that adduct 2b, if formed, would be less stable than typical TMIO adducts.
49. Beckwith, A. L. J.; Bowry, V. W.; Moad, G. J. Org. Chem. 1988, 53, 1632-1641.
50. Eaton, P. E.; Yip, Y. C. J. Am. Chem. Soc. 1991, 113, 7692-7697.
51. Choi, S.-Y.; Eaton, P. E.; Newcomb, M.; Yip, Y.-C. J. Am. Chem. Soc. 1992, 114, 6326-6329.
52. •.
53. Hermann, R. E. Ph.D. Thesis, The University of Chicago, 1987.
54. Eaton, P. E. Angew. Chem., Int. Ed. Engl. 1992, 31, 1421-1436.
55. Mendenhall, G. D. Tetrahedron Lett. 1983, 24, 451-452.
56. Nelson, D. R.; Kamataki, T.; Waxman, D. J.; Guengerich, F. P.; Estabrook, R. W.; Feyereisen, R.; Gonzalez, F. J.; Coon, M. J.; Gunsalus, I. C.; Gotoh, O.; Okuda, K.; Nebert, D. W. DNA Cell Biol. 1993, 12, 1-51.
57. -1, which is about 0.4 times as fast as rearrangement of 4.
58. Atkinson, J. K.; Ingold, K. U. Biochemistry 1993, 32, 9209-9214.
59. Rosenzweig, A. C.; Lippard, S. J. Unpublished results.
60. Tachikawa, H.; Hokari, N.; Yoshida, H. J. Phys. Chem. 1993, 97, 10035-10041.
61. Hamilton, G. A. In Molecular Mechanisms of Oxygen Activation; Hayaishi, O, Ed.; Academic: New York, 1974; pp 405-451.
62. Shteinman, A. A. FEBS Lett. 1995, 362, 5-9.
63. Shestakov, A. F.; Shilov, A. E. Submitted for publication.
64. An excellent discussion of the early evidence and current reasoning for the consensus mechanism for P-450 hydroxylation is given in ref 11.
65. Ortiz de Montellano, P. R.; Stearns, R. A. J. Am. Chem. Soc. 1987, 109, 3415-3420.
66. Newcomb, M.; Le Tadic, M.-H.; Putt, D, A.; Hollenberg, P. F. J. Am. Chem. Soc. 1995, 117, 3312-3313.
67. Holder, R. W.; Matturo, M. G. J. Org. Chem. 1977, 42, 2166-2168.
68. Crossland, R. K.; Servis, K. L. J. Org. Chem. 1970, 35, 3195-3196.
69. Eaton, P. E.; Castaldi, G. J. Am. Chem. Soc. 1985, 107, 724-726.
70. Eaton, P. E.; Wicks, G. E. J. Org. Chem. 1988, 53, 5353-5355.
71. This procedure for conversion of a diisopropylamide (nearly impossible to hydrolyze) into a carboxylic acid by first reducing the amide to the amine and subsequent oxidation with dimethyldioxirane was developed by Dr. A. Bashir-Hashemi when at The University of Chicago.
72. 74
73. Tsanaktsidis, J.; Eaton, P. E. Tetrahedron Lett. 1989, 30, 6967-6968.
74. Eaton, P. E.; Yang, C-X.; Xiong, Y. J. Am. Chem. Soc. 1990, 112, 3225-3226.
75. Coon, M. J.; van der Hoeven, T. A.; Dahl, S. B.; Haugen, D. A. Methods Enzvmol. 1978, 52.; 109-117.
76. Saito, T.; Strobel, H. W. J. Biol. Chem. 1981, 256, 984-988.
77. Strobel, H. W.; Dignam, J. D. Methods Enzymol. 1978, 52, 89-92.