Cytochrome P-450 Model Systems: Alkene Oxidation

  • Teddy G. Traylor
  • Beth E. Dunlap
  • Andrew R. Miksztal
Part of the Basic Life Sciences book series (BLSC, volume 49)


Iron(III) porphyrins efficiently catalyze the epoxidation of alkenes and the hydroxylation of alkanes by iodosylbenzenes and peracids, most likely by the same mechanisms utilized by cytochrome P-450 enzymes. The synthetic catalysts mimic the enzymes in product stereospecificity, 1 the accompanying rearrangements, 2 and the suicide labelling which results in N-alkylhemin formation.3


Iron Porphyrin Porphyrin Cation Asymmetric Epoxidation Catalytic Epoxidation Oxygen Atom Transfer 
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  1. 1.
    J. P. Collman, T. Kodadek, and J. I. Brauman, Oxygenation of styrene by cytochrome P-450 model systems: a mechanistic study, J. Am. Chem. Soc. 108:2588 (1986).CrossRefGoogle Scholar
  2. 2.
    J. T. Groves and R. S. Myers, Catalytic asymmetric epoxidations with chiral iron porphyrins, J. Am. Chem. Soc. 105:5791 (1983).CrossRefGoogle Scholar
  3. 3.
    T. Mashiko, D. Dolphin, T. Nakano, and T. G. Traylor, N-alkylporphyrin formation during the reactions of cytochrome P-450 model systems, J. Am. Chem. Soc. 107:3735 (1985).CrossRefGoogle Scholar
  4. 4.
    T. G. Traylor, T. Nakano, B. E. Dunlap, P. S. Traylor, and D. Dolphin, Mechanisms of hemin-catalyzed alkene epoxidation. The effect of catalyst on the regiochemistry of epoxidation, J. Am. Chem. Soc. 108:2782 (1986).CrossRefGoogle Scholar
  5. 5.
    T. G. Traylor and A. R. Miksztal, Mechanisms of hemin-catalyzed epoxidations: electron transfer from alkenes, J. Am. Chem. Soc. 109:2770 (1987).CrossRefGoogle Scholar
  6. 6.
    J. P. Collman, T. Kodadek, S. A. Raybuck, J. I. Brauman, and L. M. Papazian, Mechanism of oxygen atom transfer from high valent iron to olefins: implications to the biological epoxidation of olefins by cytochrome P-450, J. Am. Chem. Soc. 107:4343 (1985).CrossRefGoogle Scholar
  7. 7.
    T. G. Traylor, T. Nakano, A. R. Miksztal, and B. E. Dunlap, Transient formation of N-alkylhemins during hemin-catalyzed epoxidation of norbornene. Evidence concerning the mechanism of epoxidation, J. Am. Chem. Soc. 109:3625 (1987).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1988

Authors and Affiliations

  • Teddy G. Traylor
    • 1
  • Beth E. Dunlap
    • 1
  • Andrew R. Miksztal
    • 1
  1. 1.Department of Chemistry, D-006University of California, San DiegoLa JollaUSA

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