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Volumn 122, Issue 12, 2000, Pages 2677-2686

Cytochrome P450-catalyzed hydroxylation of mechanistic probes that distinguish between radicals and cations. Evidence for cationic but not for radical intermediates

Author keywords

[No Author keywords available]

Indexed keywords

CATION; CUBANE DERIVATIVE; CYCLOPROPANE DERIVATIVE; CYTOCHROME P450; CYTOCHROME P450 ISOENZYME; HYDROGEN PEROXIDE; IRON; OXIDE; RADICAL;

EID: 0034728622     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994106+     Document Type: Article
Times cited : (216)

References (73)
  • 1
    • 0342764516 scopus 로고    scopus 로고
    • Wayne State University
    • (a) Wayne State University.
  • 2
    • 0343634791 scopus 로고    scopus 로고
    • Department of Pharmacology, University of Michigan
    • (b) Department of Pharmacology, University of Michigan.
  • 3
    • 0342764515 scopus 로고    scopus 로고
    • Department of Biological Chemistry, University of Michigan
    • Department of Biological Chemistry, University of Michigan.
  • 10
    • 0018817225 scopus 로고
    • White, R. E.; Coon, M. J. Annu. Rev. Biochem. 1980, 49, 315-356. Groves, J. T.; Han, Y.-Z. In Cytochrome P450 Structure, Mechanism and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum: New York, 1995; pp 3-48. Guengerich, F. P.; Macdonald, T. L. FASEB J. 1990, 4, 2453-2459. 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. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
    • (1980) Annu. Rev. Biochem. , vol.49 , pp. 315-356
    • White, R.E.1    Coon, M.J.2
  • 11
    • 0018817225 scopus 로고
    • Ortiz de Montellano, P. R., Ed.; Plenum: New York
    • White, R. E.; Coon, M. J. Annu. Rev. Biochem. 1980, 49, 315-356. Groves, J. T.; Han, Y.-Z. In Cytochrome P450 Structure, Mechanism and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum: New York, 1995; pp 3-48. Guengerich, F. P.; Macdonald, T. L. FASEB J. 1990, 4, 2453-2459. 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. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
    • (1995) Cytochrome P450 Structure, Mechanism and Biochemistry, 2nd Ed. , pp. 3-48
    • Groves, J.T.1    Han, Y.-Z.2
  • 12
    • 0025307009 scopus 로고
    • White, R. E.; Coon, M. J. Annu. Rev. Biochem. 1980, 49, 315-356. Groves, J. T.; Han, Y.-Z. In Cytochrome P450 Structure, Mechanism and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum: New York, 1995; pp 3-48. Guengerich, F. P.; Macdonald, T. L. FASEB J. 1990, 4, 2453-2459. 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. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
    • (1990) FASEB J. , vol.4 , pp. 2453-2459
    • Guengerich, F.P.1    Macdonald, T.L.2
  • 13
    • 0018817225 scopus 로고
    • Coxon, J. M., Ed.; JAI Press: Greenwich CT
    • White, R. E.; Coon, M. J. Annu. Rev. Biochem. 1980, 49, 315-356. Groves, J. T.; Han, Y.-Z. In Cytochrome P450 Structure, Mechanism and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum: New York, 1995; pp 3-48. Guengerich, F. P.; Macdonald, T. L. FASEB J. 1990, 4, 2453-2459. 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. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
    • (1992) Advances in Detailed Reaction Mechanisms , vol.2 , pp. 111-147
    • Woggon, W.D.1    Fretz, H.2
  • 14
    • 0039812510 scopus 로고    scopus 로고
    • White, R. E.; Coon, M. J. Annu. Rev. Biochem. 1980, 49, 315-356. Groves, J. T.; Han, Y.-Z. In Cytochrome P450 Structure, Mechanism and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum: New York, 1995; pp 3-48. Guengerich, F. P.; Macdonald, T. L. FASEB J. 1990, 4, 2453-2459. 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. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
    • (1996) Chem. Rev. , vol.96 , pp. 2841-2887
    • Sono, M.1    Roach, M.P.2    Coulter, E.D.3    Dawson, J.H.4
  • 30
    • 0342764513 scopus 로고    scopus 로고
    • note
    • Substrate 6 was previously studied with microsomes from livers of phenobarbital-treated rats, which contain mainly P450 2B1, and the purified 2B1 isozyme (ref 19). In that study, the alcohol products were converted to acetates that were analyzed, and the amounts of products 7-OAc and 8-OAc found were comparable. Given the apparent decomposition of alcohols 7 in GC analyses, the yields of 7 relative to 8 found here are in reasonable agreement with those previously reported.
  • 36
    • 0018671537 scopus 로고
    • It is noteworthy that the concept of studying P450 hydroxylations with a probe that can differentiate between radicals and cations was put forth by Groves. Specifically, bicyclo[4.1.0]heptane was used as a probe because radicals and cations at the cyclopropylcarbinyl position of this species give different rearrangement products. P450-catalyzed hydroxylation of this probe, however, resulted in no rearrangement products. See: White, R. E.; Groves, J. T.; McClusky, G. A. Acta Biol. Med. Ger. 1979, 38, 475-489.
    • (1979) Acta Biol. Med. Ger. , vol.38 , pp. 475-489
    • White, R.E.1    Groves, J.T.2    McClusky, G.A.3
  • 44
    • 0027538424 scopus 로고
    • -1. See: Newcomb, M. Tetrahedron 1993, 49, 1151-1176.
    • (1993) Tetrahedron , vol.49 , pp. 1151-1176
    • Newcomb, M.1
  • 45
    • 0343199146 scopus 로고    scopus 로고
    • note
    • On the basis of the recalibration of PhSeH trapping kinetics (ref 30), the rate constant for rearrangement of the radical derived from probe 22 (ref 16) must be adjusted. This, in turn, results in an adjustment of the radical lifetime in the 2B1 oxidation of 22 (ref 10) from 70 to 100 fs.
  • 47
    • 0342764496 scopus 로고    scopus 로고
    • note
    • The lifetime of a transition state at ambient temperature from classical transition state theory is 170 fs.
  • 52
    • 0024569996 scopus 로고
    • Nelson, D. R.; Strobel, H. W. Biochemistry 1989, 28, 656-660. Gotoh, O.; Fujii-Kuriyama, Y. In Frontiers in Biotransformation; Ruckpaul, K., Rein, H., Eds.; Akademie: Berlin, 1989; Vol. 1. pp 195-243.
    • (1989) Biochemistry , vol.28 , pp. 656-660
    • Nelson, D.R.1    Strobel, H.W.2
  • 53
    • 0024569996 scopus 로고
    • Ruckpaul, K., Rein, H., Eds.; Akademie: Berlin
    • Nelson, D. R.; Strobel, H. W. Biochemistry 1989, 28, 656-660. Gotoh, O.; Fujii-Kuriyama, Y. In Frontiers in Biotransformation; Ruckpaul, K., Rein, H., Eds.; Akademie: Berlin, 1989; Vol. 1. pp 195-243.
    • (1989) Frontiers in Biotransformation , vol.1 , pp. 195-243
    • Gotoh, O.1    Fujii-Kuriyama, Y.2
  • 54
    • 0023645035 scopus 로고
    • Poulos, T. L.; Finzel, B. C.; Howard, A. J. J. Mol. Biol. 1987, 195, 687-700. Ravichandran, K. G.; Boddupalli, S. S.; Hasemann, C. A.; Peterson, J. A.; Deisenhofer, J. Science 1993, 261, 731-736. Hasemann, C. A.; Ravichandran, K. G.; Peterson, J. A.; Deisenhofer, J. J. Mol. Biol. 1994, 236, 1169-1185. Cupp-Vickery, J. R.; Poulos, T. L. Nat. Struct. Biol. 1995, 2, 144-153.
    • (1987) J. Mol. Biol. , vol.195 , pp. 687-700
    • Poulos, T.L.1    Finzel, B.C.2    Howard, A.J.3
  • 55
    • 0027326717 scopus 로고
    • Poulos, T. L.; Finzel, B. C.; Howard, A. J. J. Mol. Biol. 1987, 195, 687-700. Ravichandran, K. G.; Boddupalli, S. S.; Hasemann, C. A.; Peterson, J. A.; Deisenhofer, J. Science 1993, 261, 731-736. Hasemann, C. A.; Ravichandran, K. G.; Peterson, J. A.; Deisenhofer, J. J. Mol. Biol. 1994, 236, 1169-1185. Cupp-Vickery, J. R.; Poulos, T. L. Nat. Struct. Biol. 1995, 2, 144-153.
    • (1993) Science , vol.261 , pp. 731-736
    • Ravichandran, K.G.1    Boddupalli, S.S.2    Hasemann, C.A.3    Peterson, J.A.4    Deisenhofer, J.5
  • 56
    • 0028267490 scopus 로고
    • Poulos, T. L.; Finzel, B. C.; Howard, A. J. J. Mol. Biol. 1987, 195, 687-700. Ravichandran, K. G.; Boddupalli, S. S.; Hasemann, C. A.; Peterson, J. A.; Deisenhofer, J. Science 1993, 261, 731-736. Hasemann, C. A.; Ravichandran, K. G.; Peterson, J. A.; Deisenhofer, J. J. Mol. Biol. 1994, 236, 1169-1185. Cupp-Vickery, J. R.; Poulos, T. L. Nat. Struct. Biol. 1995, 2, 144-153.
    • (1994) J. Mol. Biol. , vol.236 , pp. 1169-1185
    • Hasemann, C.A.1    Ravichandran, K.G.2    Peterson, J.A.3    Deisenhofer, J.4
  • 57
    • 0029586252 scopus 로고
    • Poulos, T. L.; Finzel, B. C.; Howard, A. J. J. Mol. Biol. 1987, 195, 687-700. Ravichandran, K. G.; Boddupalli, S. S.; Hasemann, C. A.; Peterson, J. A.; Deisenhofer, J. Science 1993, 261, 731-736. Hasemann, C. A.; Ravichandran, K. G.; Peterson, J. A.; Deisenhofer, J. J. Mol. Biol. 1994, 236, 1169-1185. Cupp-Vickery, J. R.; Poulos, T. L. Nat. Struct. Biol. 1995, 2, 144-153.
    • (1995) Nat. Struct. Biol. , vol.2 , pp. 144-153
    • Cupp-Vickery, J.R.1    Poulos, T.L.2
  • 59
    • 0024832753 scopus 로고
    • Imai, M.; Shimada, H.; Watanabe, Y.; Matsushima-Hibiya, Y.; Makino, R.; Koga, H.; Horiuchi, T.; Ishimura, Y. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 7823-7827. Martinis, S. A.; Atkins, W. M.; Stayton, P. S.: Sugar, S. G. J. Am. Chem. Soc. 1989, 111, 9252-9253.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 9252-9253
    • Martinis, S.A.1    Atkins, W.M.2    Stayton, P.S.3    Sugar, S.G.4


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