Skip to main content
SpringerLink
Log in

Heme Monooxygenases

A Chemical Mechanism for Cytochrome P450 Oxygen Activation

  • Chapter
Oxygenases and Model Systems

Part of the book series: Catalysis by Metal Complexes ((CMCO,volume 19))

Abstract

Cytochrome P450 (P450)1 is a family of protoheme IX-containing monooxygenases that exhibit Soret absorption maximum around 450 nm upon combination with CO in their ferrous state. It has been known that an axial ligand in this type of hemoproteins is a cysteinyl thiolate anion. They participate in the monooxygenation reactions of a wide variety of hydrophobic substances including steroids, fatty acids, hydrocarbons, and foreign compounds such as drugs, mutagens and carcinogens [1]. More than 400 species of P450, which are all discrete entities, have been isolated from animals, plants, insects and microorganisms and have been recognized to form a gene superfamily [2]. The members of this family are known to share the following properties: (1) All of them exhibit Soret absorption maximum around 450 nm for their CO-ferrous form, 2) they can catalyze a monooxygenase type of reaction(s) by activating molecular oxygen, and 3) they share homologous nucleotide sequences in their coding region. Several enzymes such as nitric oxide synthase [3], chloroperoxidase [4], allene oxide synthase [5], thromboxane synthase [6] share some but not all of the above characteristics.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Similar content being viewed by others

References

  1. Griffin, B. W.; Peterson, J. A.; Estabrook, R. W. In The Porphyrins, D. Dolphin, Ed; Acadermic Press: London, 1979; Vol. VII; pp 333.

    Google Scholar 

  2. Nelson, D. R.; Kamataki, T.; Waxman, D. J.; Guengerich, F. P.; Estabrook, R. W.; Feyereinsen, R.; Gonzalez, F. J.; Coon, M. J.; Gotoh, O.; Okuda, K.; Nebert, D. W. DNA Cell Biol. 1993, 12, 1.

    Article  CAS  Google Scholar 

  3. Marietta, M. A. J. Biol Chem. 1993, 268, 12231.

    Google Scholar 

  4. Nuell, M. J.; Fang, G.-H.; Axley, M. J.; Kenigsberg, P.; Hager, L. P. J. Bact. 1988, 170, 1007.

    CAS  Google Scholar 

  5. Song, W.-C; Funk, C. D.; Brash, A. R. Proc. Natl. Acad. Sci. USA 1993, 90, 8519.

    Article  CAS  Google Scholar 

  6. Ullrich, V.; Hecker, M. Advances in Prostaglandin, Thromboxane, and Leukotriene Research 1990, 20, 95.

    CAS  Google Scholar 

  7. Katagiri, M.; Ganguli, B. N.; Gunsalus, I. C. J. Biol. Chem. 1968, 243, 3543.

    CAS  Google Scholar 

  8. Bradshaw, W. H.; Conrad, H. E.; Corey, E. J.; Gunsalus, I. C.; Lednicer, D. J. Am. Chem. Soc 1959, 81, 5507.

    Article  CAS  Google Scholar 

  9. Hedegaard, J.; Gunsalus, I. C. J. Biol. Chem. 1965, 240, 4038.

    CAS  Google Scholar 

  10. Ortis de Montellano, P. R. In Cytochrome P-450: Structure, Mechanism, and Biochemistry, P. R. Ortis de Montellano, Ed.; Plenum Press: New York and London, 1986; pp 217.

    Google Scholar 

  11. Koga, H.; Rauchfuss, B.; Gunsalus, I. C. Biochem. Biophys. Res. Commun. 1985, 130, 412.

    Article  CAS  Google Scholar 

  12. Unger, B. P.; Gunsalus, I. C.; Sligar, S. G. J. Biol. Chem. 1986, 261, 1158.

    CAS  Google Scholar 

  13. Poulos, T. L.; Finzel, B. C.; Howard, A. J. Biochemistry 1986, 25, 5314.

    Article  CAS  Google Scholar 

  14. Poulos, T. L.; Finzel, B. C.; Howard, A. J. J. Mol. Biol. 1987, 195, 687.

    Article  CAS  Google Scholar 

  15. Gerber, N. C.; Sligar, S. G. J. Biol. Chem. 1994, 269, 4260.

    CAS  Google Scholar 

  16. Gunsalus, I. C.; Meeks, J. R.; Lipscomb, J. D.; Debrunner, P.; Münck, E. In Molecular Mechanisms of Oxygen Activation, O. Hayaishi, Ed.; Academic Press: New York, 1974; pp 559.

    Google Scholar 

  17. Sligar, S. G.; Gunsalus, I. C. Proc. Natl. Acad. Sci. USA 1976, 73, 1078.

    Article  CAS  Google Scholar 

  18. Pederson, T. C.; Austin, R. H.; Gunsalus, I. C. In Microsomes and Drug Oxidations, V. Ullrich, I. Roots, A. Hildebrandt, R. W. Estabrook and A. H. Conney, Ed.; Pergamon Press: Oxford, 1977; pp 275.

    Google Scholar 

  19. Hui Bon Hoa, G.; Begard, E.; Debey, P.; Gunsalus, I. C. Biochemistry 1978, 17, 2835.

    Article  CAS  Google Scholar 

  20. Hintz, M. J.; Peterson, J. A. J. Biol. Chem. 1981, 256, 6721.

    CAS  Google Scholar 

  21. Davies, M. D.; Sligar, S. G. Biochemistry 1992, 31, 11383.

    Article  CAS  Google Scholar 

  22. Hintz, M. J.; Mock, D. M.; Peterson, L. L.; Tuttle, K.; Peterson, J. A. J. Biol. Chem. 1982, 257, 14324.

    CAS  Google Scholar 

  23. Stayton, P. S.; Sligar, S. G. Biochemistry 1990, 29, 7386.

    Article  Google Scholar 

  24. Koga, H.; Sagara, Y.; Yaoi, T.; Tsujimura, M.; Nakamura, K.; Sekimizu, K.; Makino, R.; Shimada, H.; Ishimura, Y.; Yura, K.; Go, M.; Ikeguchi, M.; Horiuchi, T.FEBS Lett. 1993,331, 109.

    Google Scholar 

  25. Nakamura, K.; Horiuchi, T.; Yasukochi, T.; Sekimizu, K.; Hara, T.; Sagara, Y. Biochim. Biophys. Acta 1994, 1207, 40.

    Article  CAS  Google Scholar 

  26. Sligar, S. G.; Debrunner, P. G.; Lipscomb, J. D.; Namtvedt, M. J.; Gunsalus, I. C. Proc. Natl. Acad. Sci. USA 1974, 71, 3906.

    Article  CAS  Google Scholar 

  27. Stayton, P. S.; Sligar, S. G. Biochemistry 1991, 30, 1845.

    Article  CAS  Google Scholar 

  28. Pochapsky, T. C.; Ye, X. M.; Ratnaswamy, G.; Lyons, T. A. Biochemistry 1994, 33, 6424.

    Article  CAS  Google Scholar 

  29. Pochapsky, T. C.; Ratnaswamy, G.; Patera, A. Biochemistry 1994, 33, 6433.

    Article  CAS  Google Scholar 

  30. Geren, L.; Tuls, J.; O’Brien, P.; Millett, F.; Peterson, J. A. J. Biol. Chem. 1986, 261, 15491.

    CAS  Google Scholar 

  31. Ishimura, Y.; Ullrich, V.; Peterson, J. A. Biochem. Biophys. Res. Commun. 1971, 42, 140.

    Article  CAS  Google Scholar 

  32. Peterson, J. A.; Ishimura, Y.; Griffin, B. W. Arch. Bioch. Biophys. 1972, 149, 197.

    Article  CAS  Google Scholar 

  33. Tyson, C. A.; Lipscomb, J. D.; Gunsalus, I. C. J. Biol. Chem. 1972, 247, 5777.

    CAS  Google Scholar 

  34. Eisenstein, L.; Debey, P.; Douzou, P. Biochem. Biophys. Res. Commun. 1977, 77, 1377.

    Article  CAS  Google Scholar 

  35. Lipscomb, J. D.; Sligar, S. G.; Namtvedt, M. J.; Gunsalus, I. C. J. Biol. Chem. 1976, 251, 1116.

    CAS  Google Scholar 

  36. Sligar, S. G.; Lipscomb, J. D.; Debrunner, P. G.; Gunsalus, I. C. Biochem. Biophys. Res. Commun. 1974, 61, 290.

    Article  CAS  Google Scholar 

  37. Guengerich, F. P.; Ballou, D. P.; Coon, M. J. Biochem. Biophys. Res. Commun. 1976, 70, 951.

    Article  CAS  Google Scholar 

  38. Sevrioukova, I. F.; Peterson, J. A. Arch. Biochem. Biophys. 1995, 317, 397.

    Article  CAS  Google Scholar 

  39. Bangcharoenpaurpong, O.; Rizos, A. K.; Champion, P. M.; Jollie, D.; Sligar, S. G. J. Biol. Chem. 1986, 261, 8089.

    CAS  Google Scholar 

  40. Nishimura, Y.; Makino, R.; Imai, M.; Shimada, H.; Koga, H.; Horiuchi, T.; Ishimura, Y. In Proceedings of the Xllth International conference on Raman Spectroscopy, J. R. During and J. F. Sullivan, Ed.; John Wiley & Sons: New York, 1990; pp 702.

    Google Scholar 

  41. Egawa, T.; Ogura, T.; Makino, R.; Ishimura, Y.; Kitagawa, T. J. Biol. Chem. 1991, 266, 10246.

    CAS  Google Scholar 

  42. Brewer, C. B.; Peterson, J. A. J. Biol. Chem. 1988, 263, 791.

    CAS  Google Scholar 

  43. Makino, R.; Iizuka, T.; Sakaguchi, K.; Ishimura, Y. In Oxygenases and Oxygen Metabolism, M. Nozaki, S. Yamamoto, Y. Ishimura, M. J. Coon, L. Ernster and R. W. Estabrook, Ed.; Academic Press: New York, 1982; pp 467.

    Google Scholar 

  44. Debey, P.; Balny, C. Biochem. Soc. Trans. 1978, 6, 1289.

    CAS  Google Scholar 

  45. Eble, K. S.; Dawson, J. H. Biochemistry 1984, 23, 2068.

    Article  CAS  Google Scholar 

  46. Ishimura, Y.; Makino, R.; Iizuka, T.; Shimada, H. In Cytochrome P-450: New Trend, R. Sato, T. Omura, Y. Imai and Y. Fujii-Kuriyama, Ed.; Yamada Science Foundation: 1987; pp 151.

    Google Scholar 

  47. Shiro, Y.; Iizuka, T.; Makino, R.; Ishimura, Y.; Morishima, I. J. Am. Chem. Soc. 1989, 111, 7707.

    Article  CAS  Google Scholar 

  48. Poulos, T. L.; Kraut, J. J. Biol. Chem. 1980, 255, 8199.

    CAS  Google Scholar 

  49. Dawson, J. H. Science 1988, 240, 433.

    Article  CAS  Google Scholar 

  50. Patzetl, H.; Woggon, W.-D. Helv. Chim. Acta 1992, 75, 523.

    Article  Google Scholar 

  51. Hamilton, G. A. In Molecular Mechanisms of Oxygen Activation, O. Hayaishi, Ed.; Academic Press: New York, 1974; pp 405.

    Google Scholar 

  52. Groves, J. T.; Watanabe, Y.; McMurray, T. J. J. Am. Chem. Soc. 1983, 105, 4489.

    Article  CAS  Google Scholar 

  53. Khenkin, A. M.; Shteinman, A. A. In J. Chem. Soc., Chem. Commun,; 1984; pp 1219.

    Google Scholar 

  54. McCandlish, E.; Miksztal, A. R.; Nappa, M.; Sprenger, A. Q.; Valentine, J. S.; Stong, J. D.; Spiro, T. G. J. Am. Chem. Soc. 1980, 102, 4268.

    Article  CAS  Google Scholar 

  55. Shirazi, A.; Goff, H. M. J. Am. Chem. Soc. 1982, 104, 6318.

    Article  CAS  Google Scholar 

  56. Welborn, C. H.; Dolphin, D.; James, B. R. J. Am. Chem. Soc. 1981, 103, 2869.

    Article  CAS  Google Scholar 

  57. White, R. E.; Coon, M. J. Anna. Rev. Biochem. 1980, 49, 315.

    Article  CAS  Google Scholar 

  58. Rahimtula, A. D.; O’Brien, P. J.; Hrycay, E. G.; Peterson, J. A.; Estabrook, R. W. Biochem. Biophys. Res. Commun. 1974, 60, 695.

    Article  CAS  Google Scholar 

  59. Wagner, G. C.; Palcic, M. M.; Dunford, H. B. FEBS Lett. 1983, 156, 244.

    Article  CAS  Google Scholar 

  60. Kobayashi, K.; Amano, M.; Kanbara, Y.; Hayashi, K. J. Biol. Chem. 1987, 262, 5445.

    CAS  Google Scholar 

  61. Shimizu, T.; Murakami, Y.; Hatano, M. J. Biol. Chem. 1994, 269, 13296.

    CAS  Google Scholar 

  62. Groves, J. T.; Haushalter, R. C.; Nakamura, M.; Nemo, T. E.; Evans, B. J. J. Am. Chem. Soc. 1981, 103, 2884.

    Article  CAS  Google Scholar 

  63. White, P. W. Bioorg. Chem. 1990, 18, 440.

    Article  CAS  Google Scholar 

  64. Groves, J. T. J. Chem. Educ. 1985, 62, 928.

    Article  CAS  Google Scholar 

  65. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5699.

    Article  CAS  Google Scholar 

  66. Newcomb, M.; Le Tadic, M.-H.; Putt, D. A.; Hollenberg, P. F. J. Am. Chem. Soc. 1995, 117, 3312.

    Article  CAS  Google Scholar 

  67. Atkins, W. M.; Sligar, S. G. Biochemistry 1988, 27, 1610.

    Article  CAS  Google Scholar 

  68. Egawa, T.; Shimada, H.; Ishimura, Y. Biochem. Biophys. Res. Commun. 1994, 201, 1464.

    Article  CAS  Google Scholar 

  69. Palcic, M. M.; Rutter, R.; Araiso, T.; Hager, L. P.; Dunford, H. B. Biochem. Biophys. Res. Commun. 1980, 94, 1123.

    Article  CAS  Google Scholar 

  70. Nelson, D. R.; Strobel, H. W. Mol. Biol. Evol. 1987, 4, 572.

    CAS  Google Scholar 

  71. Goto, O.; Fujii-Kuriyama, Y. In Frontiers in Biotransformation, K. Ruckpaul and H. Rein, Ed.; Akademie-Verlag: Berlin, 1989; Vol. 1; pp 195.

    Google Scholar 

  72. Garfinkel, D. Arch. Biochem. Biophys. 1958, 77, 493.

    Article  CAS  Google Scholar 

  73. Klingenberg, M. Arch. Biochem. Biophys. 1958, 75, 376.

    Article  CAS  Google Scholar 

  74. Omura, T.; Sato, R. J. Biol. Chem. 1964, 239, 2370.

    CAS  Google Scholar 

  75. Hanson, L. K.; Eaton, W. A.; Sligar, S. G.; Gunsalus, I. C.; Gouterman, M.; Connell, C. R. J. Am. Chem. Soc. 1976, 98, 2672.

    Article  CAS  Google Scholar 

  76. Raag, R.; Poulos, T. L. Biochemistry 1989, 28, 7586.

    Article  CAS  Google Scholar 

  77. Raag, R.; Martinis, S. A.; Sligar, S. G.; Poulos, T. L. Biochemistry 1991, 30, 11420.

    Article  CAS  Google Scholar 

  78. 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.

    Article  CAS  Google Scholar 

  79. Martinis, S. A.; Atkins, W. M.; Stayton, P. S.; Sligar, S. G. J. Am. Chem. Soc. 1989, 111, 9252.

    Article  CAS  Google Scholar 

  80. Shimada, H.; Makino, R.; Unno, M.; Horiuchi, T.; Ishimura, Y. In Cytochrome P450 Biochemistry, Biophysics and Molecular Biology, M. C. Lechner, Ed.; John Libbey Eurotext: Paris, 1993; pp 299.

    Google Scholar 

  81. Makino, R.; Shimada, H. In Cytochrome P450, second edition, T. Omura, Y. Ishimura and Y. Fujii-Kuriyama, Ed.; Kodansha: Tokyo, 1993; pp 17.

    Google Scholar 

  82. Nishimoto, M.; Gotoh, O.; Okuda, K.; Noshiro, M. J. Biol. Chem. 1991, 266, 6467.

    CAS  Google Scholar 

  83. Harris, D. L.; Loew, G. H. J. Am. Chem. Soc. 1994, 116, 11671.

    Article  CAS  Google Scholar 

  84. Furuya, H.; Shimizu, T.; Hirano, K.; Hatano, M.; Fujii-Kuriyama, Y.; Raag, R.; Poulos, T. L. Biochemistry 1989, 28, 6848.

    Article  CAS  Google Scholar 

  85. Ishigooka, M.; Shimizu, T.; Hiroya, K.; Hatano, M. Biochemistry 1992, 31, 1528.

    Article  CAS  Google Scholar 

  86. Imai, Y.; Nakamura, M. Biochem. Biophys. Res. Commun. 1989, 158, 717.

    Article  CAS  Google Scholar 

  87. Fukuda, T.; Imai, Y.; Komori, M.; Nakamura, M.; Kusunose, E.; Satouchi, K.; Kusunose, M. J. Biochem. 1993, 113, 7.

    CAS  Google Scholar 

  88. Yeom, H.; Sligar, S. G.; Li, H.; Poulos, T. L.; Fulco, A. J. Biochemistry 1995, 34, 14733.

    Article  CAS  Google Scholar 

  89. Ravichandran, K. G.; Boddupalli, S. S.; Hasemann, C. A.; Peterson, J. A.; Deisenhofer, J. Science 1993, 261, 731.

    Article  CAS  Google Scholar 

  90. Li, H.; Poulos, T. L. Acta. Cryst. 1995, D51, 21.

    CAS  Google Scholar 

  91. Kimata, Y.; Shimada, H.; Hirose, T.; Ishimura, Y. Biochem. Biophys. Res. Commun. 1995, 208, 96.

    Article  CAS  Google Scholar 

  92. Shimada, H.; Makino, R.; Imai, M.; Horiuchi, T.; Ishimura, Y. In International Symposium on Oxygenases and Oxygen Activation, S. Yamamoto, M. Nozaki and Y. Ishimura, Ed.; Yamada Science Foundation: 1990; pp 133.

    Google Scholar 

  93. Gerber, N. C.; Sligar, S. G. J. Am. Chem. Soc. 1992, 114, 8742.

    Article  CAS  Google Scholar 

  94. Zhou, D.; Korzekwa, K. R.; Poulos, T.; Chen, S. J. Biol. Chem. 1992, 267, 762.

    CAS  Google Scholar 

  95. Makino, R.; Shimada, H.; Okada, Y.; Horiuchi, T.; Ishimura, Y. unpublished observation.

    Google Scholar 

  96. Miki, H.; Egawa, T.; Shimada, H.; Makino, R.; Kitagawa, T.; Horiuchi, T.; Ishimura, Y. Oxy Asn251-P450cam exhibited an o-o stretch frequency at 1136 ±2 cm-1, comparing with 1140 cmst-1 for the native P450cam (unpublished observation).

    Google Scholar 

  97. Poulos, T. L.; Howard, A. J. Biochemistry 1987, 26, 8165.

    Article  CAS  Google Scholar 

  98. Noren, C. J.; Anthony-Cahill, S. J.; Griffith, M. C.; Schultz, P. G. Science 1989, 244, 182.

    Article  CAS  Google Scholar 

  99. Shimada, H.; Kimata, Y.; Kanamori, Y.; Egawa, T.; Ishimura, Y. 1996, manuscript in preparation.

    Google Scholar 

  100. Di Primo, C.; Sligar, S. G.; Hui Bon Hoa, G.; Douzou, P. FEBS Lett. 1992, 312, 252.

    Article  Google Scholar 

  101. Aikens, J.; Sligar, S. G. J. Am. Chem. Soc. 1994, 116, 1143.

    Article  CAS  Google Scholar 

  102. Schowen, R. L. In Isotope Effects on Enzyme-Catalyzed Reactions, W. W. Cleland, M. H. O’Leary and D. B. Northlop, Ed.; University Park Press: Baltimore, 1977; pp 64.

    Google Scholar 

  103. Robinson, C. R.; Sligar, S. G. J. Mol. Biol. 1993, 234, 302.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Biochemistry, School of Medicine, Keio University, 35 Shinanomachi, Shinjuku-ku, Tokyo, 160, JAPAN

    Hideo Shimada & Yuzuru Ishimura

  2. Beckman Institute for Advanced Science and Technology, University of Illinois, 405 North Mathews, Urbana, IL, 61801, USA

    Stephen G. Sligar & Hyeyeong Yeom

Authors
  1. Hideo Shimada
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Stephen G. Sligar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hyeyeong Yeom
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yuzuru Ishimura
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Kyoto University, Kyoto, Japan

    Takuzo Funabiki

Rights and permissions

Reprints and permissions

Copyright information

© 1997 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Shimada, H., Sligar, S.G., Yeom, H., Ishimura, Y. (1997). Heme Monooxygenases. In: Funabiki, T. (eds) Oxygenases and Model Systems. Catalysis by Metal Complexes, vol 19. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-5442-0_5

Download citation

  • DOI: https://doi.org/10.1007/978-94-011-5442-0_5

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-6289-3

  • Online ISBN: 978-94-011-5442-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation