Skip to main content
Log in

The role of metal-oxygen intermediates in biological and chemical monooxygenation of alkanes

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The role of metal-peroxo, -hydroperoxo, and -oxo intermediates in activation of O2 and transfer of an oxygen atom to the C—H bond in biocatalysis by heme and non-heme monooxygenases and biomimetic oxidation of alkanes is reviewed.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Cytochrome P-450: Structure, Mechanism, and Biochemistry, 2nd ed., Ed. P. R. Ortiz de Montellano, Plenum Press, New York, 1995.

    Google Scholar 

  2. M. Sono, M. P. Roach, E. D. Coulter, and J. D. Dowson, Chem. Rev., 1996, 96, 2841.

    Google Scholar 

  3. N. L. Poulos, B. C. Finzel, and P. J. Howard, J. Mol. Biol., 1987, 195, 687.

    Google Scholar 

  4. I. Schlichting, C. Jung, and H. Schulze, FEBS Lett., 1997, 415, 253.

    Google Scholar 

  5. D. Harris, G. Loew, and L. Waskell, J. Am. Chem. Soc., 1998, 120, 4308.

    Google Scholar 

  6. T. Ueno, Y. Kousumi, K. Yoshizawa-Kumagaye, K. Nakajima, N. Ueyama, T. Okamura, and A. Nakamura, J. Am. Chem. Soc., 1998, 120, 12264.

    Google Scholar 

  7. M. Matsu-ura, F. Tani, S. Nakayama, N. Nakamura, and Y. Naruta, Angew. Chem., Int. Ed. Engl., 2000, 39, 1989.

    Google Scholar 

  8. G. H. Loew and D. L. Harris, Chem. Rev., 2000, 100, 407.

    Google Scholar 

  9. D. E. Benson, K. S. Suslick, and S. G. Sligar, Biochemistry, 1997, 36, 5104.

    Google Scholar 

  10. D. Mandon, R. Weiss, M. Franke, E. Bill, and A. X. Trautwein, Angew. Chem., Int. Ed. Engl., 1989, 28, 1709.

    Google Scholar 

  11. A. M. Khenkin and A. A. Shteinman, J. Chem. Soc., Chem. Commun., 1984, 1219.

  12. Y. Watanabe, in The Porphyrin Handbook, Eds. K. M. Kadish, K. M. Smith, and R. Guilard, Vol. 4, Academic Press, 2000, 97.

  13. I. Schlichting, J. Berendzen, K. Chu, A. M. Stock, S. A. Maves, D. A. Benson, R. M. Sweet, D. Ringe, G. A. Petsko, and S. G. Sligar, Science, 2000, 287, 1615.

    Google Scholar 

  14. S. L. Edwards, H. X. Nguyen, R. C. Hamlin, and J. Kraut, Biochemistry, 1987, 26, 1503.

    Google Scholar 

  15. Y. Urano, T. Higuchi, M. Hirobe, and T. Nagano, J. Am. Chem. Soc., 1997, 119, 12008.

    Google Scholar 

  16. N. Suzuki, T. Higuchi, Y. Urano, K. Kikuchi, H. Uekusa, Y. Ohashi, T. Uchida, T. Kitagawa, and T. Nagano, J. Am. Chem. Soc., 1999, 121, 11571.

    Google Scholar 

  17. P. M. Champion, J. Am. Chem. Soc., 1989, 111, 3433.

    Google Scholar 

  18. M. Filatov, N. Harris, and S. Shaik, J. Chem. Soc., Perkin Trans. 2, 1999, 399.

  19. E. I. Solomon, T. C. Brunold, M. I. Davis, J. N. Kemsley, S.-K. Lee, N. Lehnert, F. Neese, A. J. Skulan, Y.-S. Yang, and J. Zhou, Chem. Rev., 2000, 100, 235.

    Google Scholar 

  20. B. J. Wallar and J. D. Lipscomb, Chem. Rev., 1996, 96, 2625.

    Google Scholar 

  21. K. E. Liu and S. J. Lippard, in Advances in Inorganic Chemistry, 42, Ed. A. G. Sykes, Acad. Press, Inc., San Diego, CA, 1995, 263.

    Google Scholar 

  22. N. Elango, R. Radhakrishnan, W. A. Froland, B. J. Wallar, C. A. Earhart, J. D. Lipscomb, and D. H. Ohlendorf, Protein Science, 1997, 6, 556.

    Google Scholar 

  23. A. C. Rosenzweig, P. Nordlund, P. M. Takahara, C. A. Frederick, and S. J. Lippard, Chem. Biol., 1995, 2, 409.

    Google Scholar 

  24. L. Shu, Y. Liu, J. D. Lipscomb, and L. Que, J. Biol. Inorg. Chem., 1996, 1, 297.

    Google Scholar 

  25. B. J. Brazeau and J. D. Lipscomb, Biochemistry, 2000, 39, 13503.

    Google Scholar 

  26. A. M. Valentine, S. S. Stahl, and S. J. Lippard, J. Am. Chem. Soc., 1999, 121, 3876.

    Google Scholar 

  27. L. Shu, J. C. Nesheim, K. Kauffmann, E. Münck, J. D. Lipscomb, and L. Que, Jr., Science, 1997, 275, 515.

    Google Scholar 

  28. L. Que, Jr., J. Chem. Soc., Dalton Trans., 1997, 3933.

  29. A. A. Shteinman, Izv. Akad. Nauk, Ser. Khim., 1997, 1676 [Russ. Chem. Bull., 1997, 46, 1599 (Engl. Transl.)].

  30. P. E. M. Siegbahn, J. Biol. Inorg. Chem., 2001, 6, 27.

    Google Scholar 

  31. S. C. Gallagher, A. J. Callaghan, J. Zhao, H. Dalton, and J. Trewhella, Biochemistry, 1999, 38, 6752.

    Google Scholar 

  32. A. A. Shteinman, FEBS Lett., 1995, 362, 5.

    Google Scholar 

  33. S.-K. Lee and J. D. Lipscomb, Biochemistry, 1999, 38, 4423.

    Google Scholar 

  34. B. D. Dunietz, M. D. Beachy, Y. Cao, D. A. Whittington, S. J. Lippard, and R. A. Friesner, J. Am. Chem. Soc., 2000, 122, 2828.

    Google Scholar 

  35. H. Busch, K. Mogi, G. D. Musaev, and K. Morokuma, J. Am. Chem. Soc., 1999, 121, 7249.

    Google Scholar 

  36. P. Broun, J. Shanklin, E. Whittle, and C. Somerville, Science, 1998, 282, 1315.

    Google Scholar 

  37. J. Shanklin, C. Achim, H. Schmidt, B. Fox, and E. Munck, Proc. Natl. Acad. Sci. U. S. A., 1997, 94, 2981.

    Google Scholar 

  38. A. G. Catopodis, K. Wimalasena, J. Lee, and S. W. May, J. Am. Chem. Soc., 1984, 106, 7928.

    Google Scholar 

  39. A. D. N. Vaz, D. F. McGinnity, and M. J. Coon, Proc. Natl. Acad. Sci. U. S. A., 1998, 95, 3555.

    Google Scholar 

  40. P. H. Toy, M. Newcomb, M. J. Coon, and A. D. N. Vaz, J. Am. Chem. Soc., 1998, 120, 9718.

    Google Scholar 

  41. M. Newcomb and P. H. Toy, Acc. Chem. Res., 2000, 33, 449.

    Google Scholar 

  42. R. Davidov, R. Kappl, J. Huttermann, and J. A. Peterson, FEBS Lett, 1991, 295, 113.

    Google Scholar 

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

    Google Scholar 

  44. E. McCandish, A. R. Mikztal, M. Nappa, A. Q. Sprenger, J. S. Valentine, D. Stong, and T. G. Spiro, J. Am. Chem. Soc., 1980, 102, 4268.

    Google Scholar 

  45. I. B. Afanas'ev, S. V. Prigoda, A. M. Khenkin, and A. A. Shteinman, Dokl. Akad. Nauk SSSR, 1977, 236, 641.

    Google Scholar 

  46. M. Selke and J. S. Valentine, J. Am. Chem. Soc., 1998, 120, 2652.

    Google Scholar 

  47. A. M. Khenkin and A. A. Shteinman, Kinet. Katal., 1982, 219 [Kinet. Catal., 1982, ?? (Engl. Transl.)].

  48. V. K. Koltover, A. M. Khenkin, and A. A. Shteinman, Izv. Akad. Nauk, Ser. Khim., 1978, 1690 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1978, ?? (Engl. Transl.)].

  49. D. D. LeCloux, A. M. Barrios, T. J. Mizoguchi, and S. J. Lippard, J. Am. Chem. Soc., 1998, 120, 9001.

    Google Scholar 

  50. T. Ookubo, H. Sugimoto, T. Nagayama, H. Masuda, T. Sato, K. Tanaka, Y. Maeda, H. Okawa, Y. Hayashi, A. Uehara, and M. Suzuki, J. Am. Chem. Soc., 1996, 118, 701.

    Google Scholar 

  51. Y. Dong, S. Yan, V. G. Young, and L. Que, Jr., Angew. Chem., Int. Ed. Engl., 1997, 35, 618.

    Google Scholar 

  52. K. Kim and S. J. Lippard, J. Am. Chem. Soc., 1996, 118, 4914.

    Google Scholar 

  53. A. J. Simaan, F. Banse, P. Mialane, A. Boussac, S. Un, T. Kargar-Grisel, G. Bouchoux, and J.-J. Girerd, Eur. J. Inorg. Chem., 1999, 993.

  54. M. Costas, K. Chen, and L. Que, Jr., Coord. Chem. Rev., 2000, 200–202, 517.

    Google Scholar 

  55. A. P. Sobolev, D. E. Babushkin, and E. P. Talsi, J. Mol. Catal. (A), 2000, 159, 233.

    Google Scholar 

  56. R. Y. N. Ho, G. Roelfes, B. Feringa, and L. Que, J. Am. Chem. Soc., 1999, 121, 264.

    Google Scholar 

  57. W. Nam, M. H. Lim, S. K. Moon, and C. Kim, J. Am. Chem. Soc., 2000, 122, 10805.

    Google Scholar 

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

    Google Scholar 

  59. J. E. Penner-Hahn, K. S. Eble, T. J. McMurry, M. Renner, A. L. Balch, J. T. Groves, J. H. Dawson, and K. O. Hodgson, J. Am. Chem. Soc., 1986, 108, 7819.

    Google Scholar 

  60. T. Egawa, H. Shimada, and Y. Ishimura, Biochem. Biophys. Res. Commun., 1994, 201, 1464.

    Google Scholar 

  61. F. Ogliaro, S. Cohen, M. Filatov, N. Harris, and S. Shaik, Angew. Chem. Intern. Ed. Engl., 2000, 39, 3851.

    Google Scholar 

  62. C. E. Schulz, R. Rutter, J. T. Sage, P. G. Debrunner, and L. P. Hager, Biochemistry, 1984, 23, 4734.

    Google Scholar 

  63. T. Wolter, W. Meyer-Klaucke, M. Muther, D. Mandon, H. Winkler, A. X. Trautwein, and R. Weiss, J. Inorg. Biochem., 2000, 117.

  64. J. T. Groves, J. Lee, and S. S. Maria, J. Am. Chem. Soc., 1997, 119, 6269.

    Google Scholar 

  65. A. Sorokin, A. Robert, and B. Meunier, J. Am. Chem. Soc., 1993, 115, 7293.

    Google Scholar 

  66. M. H. Lim, Y. J. Li, Y. M. Goh, W. Nam, and C. Kim, Bull. Chem. Soc. Jpn, 1999, 72, 707.

    Google Scholar 

  67. W. Nam, M. H. Lim, S.-Y. Oh, J. H. Lee, H. J. Lee, S. K. Woo, C. Kim, and W. Shin, Angew. Chem. Intern. Ed. Engl., 2000, 39, 3646.

    Google Scholar 

  68. J. T. Groves, Z. Gross, and M. K. Stern, Inorg. Chem., 1994, 33, 5065.

    Google Scholar 

  69. C. A. Grapperhaus, B. Mienert, E. Bill, T. Weyhermüller, and K. Wieghardt, Inorg. Chem., 2000, 39, 5306.

    Google Scholar 

  70. K. Chen and L. Que, J. Chem. Soc., Chem. Commun., 1999, 1375.

  71. V. S. Kulikova, O. N. Gritsenko, and A. A. Shteinman, Mendeleev Commun., 1996, 119.

  72. H.-F. Hsu, Y. Dong, L. Shu, V. G. Young, Jr., and L. Que, Jr., J. Am. Chem. Soc., 1999, 121, 5230.

    Google Scholar 

  73. V. MacMurdo, H. Cheng, and L. Que, Jr., Inorg. Chem., 2000, 39, 2254.

    Google Scholar 

  74. D. Lee, J. D. Bois, D. Petasis, M. P. Hendrich, C. Krebs, B. H. Huynh, and S. J. Lippard, J. Am. Chem. Soc., 1999, 121, 9893.

    Google Scholar 

  75. C. Kim, Y. Dong, and L. Que, Jr., J. Am. Chem. Soc., 1997, 119, 3635.

    Google Scholar 

  76. H. Zheng, S. J. Yoo, E. Münck, and L. Que, Jr., J. Am. Chem. Soc., 2000, 122, 3789.

    Google Scholar 

  77. A. E. Shilov, and A. A. Shteinman, Acc. Chem. Res., 1999, 32, 763.

    Google Scholar 

  78. A. A. Shteinman, J. Biol. Inorg. Chem., 1998, 4, 304.

    Google Scholar 

  79. J. L. McLain, J. Lee, and J. T. Groves, in Biomimetic Oxidations Catalyzed by Transition Metal Complexes, Ed. B. Meunier, Imperial College Press: London, 2000, 91.

    Google Scholar 

  80. A. F. Shestakov and A. E. Shilov, J. Mol. Cat. (A), 1996, 105, 1.

    Google Scholar 

  81. A. M. Valentine, M.-H. LeTadic-Biadatti, P. H. Toy, M. Newcomb, and S. J. Lippard, J. Biol. Chem., 2000, 274, 10771.

    Google Scholar 

  82. N. D. Priestley, H. G. Floss, W. A. Froland, J. D. Lipscomb, P. G. Williams, and H. Morimoto, J. Am. Chem. Soc., 1992, 114, 7561.

    Google Scholar 

  83. A. M. Valentine, B. Wilkinson, K. E. Liu, S. Komar Panicucci, N. D. Priestley, P. G. Williams, H. Morimoto, H. G. Floss, and S. J. Lippard, J. Am. Chem. Soc., 1997, 119, 1818.

    Google Scholar 

  84. S.-Y. Choi, P. E. Eaton, D. A. Kopp, S. J. Lippard, M. Newcomb, and R. Shen, J. Am. Chem. Soc., 1999, 121, 12198.

    Google Scholar 

  85. E. I. Karasevich, A. F. Shestakov, and A. E. Shilov, Kinet. Katal., 1997, 38, 852 [Kinet. Catal., 1997, 38, 782 (Engl. Transl.)].

    Google Scholar 

  86. K. Yoshizawa, J. Inorg. Biochem., 2000, 78, 23.

    Google Scholar 

  87. Y.-M. Chen, D. E. Clemmer, and P. B. Armentrout, J. Am. Chem. Soc., 1994, 116, 7815.

    Google Scholar 

  88. D. Schroder, A. Fiedler, J. Hrusak, and H. Schwarz, J. Am. Chem. Soc., 1992, 114, 1215.

    Google Scholar 

  89. R. N. Austin, H.-K. Chang, G. J. Zylstra, and J. T. Groves, J. Am. Chem. Soc., 2000, 122, 11747.

    Google Scholar 

  90. E. Caspi, J. Piper, and S. Shapiro, J. Chem. Soc., Chem. Commun., 1981, 76.

  91. J. I. Manchester, J. P. Dinocenzo, L. A. Higgins, and J. P. Jones, J. Am. Chem. Soc., 1997, 119, 5069.

    Google Scholar 

  92. F. Ogliaro, N. Harris, S. Cohen, M. Filatov, S. P. de Visser, and S. Shaik, J. Am. Chem. Soc., 2000, 122, 8977.

    Google Scholar 

  93. V. M. Trukhan, O. N. Gritsenko, E. Nordlander, and A. A. Shteinman, J. Inorg. Biochem., 2000, 79, 41.

    Google Scholar 

  94. V. M. Trukhan, E. Nordlander, and A. A. Shteinman, Zh. Org. Khim., 1999, 334 [Russ. J. Org. Chem., 1999, 315 (Engl. Transl.)].

  95. V. M. Trukhan, C. G. Pierpont, K. B. Jensen, E. Nordlander, and A. A. Shteinman, J. Chem. Soc., Chem. Commun., 1999, 1193.

  96. V. M. Trukhan, V. V. Polukhov, I. V. Sulimenkov, N. S. Ovanesyan, N. A. Koval'chuk, A. F. Dodonov, and A. A. Shteinman, Kinet. Katal., 1998, 39, 858 [Kinet. Catal., 1998, 39, 788 (Engl. Transl.)].

    Google Scholar 

  97. A. E. Shilov, Metal Complexes in Biomimetic Chemical Reactions.; CRC Press: New York, 1997.

    Google Scholar 

  98. E. I. Karasevich, V. S. Kulikova, A. E. Shilov, and A. A. Shteinman, Usp. Khim., 1998, 67, 376 [Russ. Chem. Rev., 1998, 67, 335 (Engl. Transl.)].

    Google Scholar 

  99. A. M. Khenkin and A. A. Shteinman, Ross. Khim. Zh., 1995, 39, 41 [Mendeleev Chemistry Journal, 1995, 39, 1 (Engl. Transl.)].

    Google Scholar 

  100. R. A. Sheldon, in Biomimetic Oxidations Catalyzed by Transition Metal Complexes, Ed. B. Meunier, Imperial College Press: London, 2000, 613.

    Google Scholar 

  101. J. T. Groves and T. E. Nemo, J. Am. Chem. Soc., 1983, 105, 6243.

    Google Scholar 

  102. D. Mansuy, J. F. Bartoli, and M. Momenteau, Tetrahedron Lett., 1982, 23, 2781.

    Google Scholar 

  103. J. F. Bartoli, P. Battioni, W. R. DeFoor, and D. Mansuy, J. Chem. Soc., Chem. Commun., 1994, 23.

  104. M. J. Nappa, C. A. Tolman, Inorg. Chem., 1985, 24, 4711.

    Google Scholar 

  105. A. M. Khenkin and A. A. Shteinman, Kinet. Katal., 1989, 30, 7 [Kinet. Catal, 1989, 30 (Engl. Transl.)].

    Google Scholar 

  106. B. R. Cook, T. J. Reinert, and K. S. Suslik, J. Am. Chem. Soc., 1986, 108, 7281.

    Google Scholar 

  107. A. B. Sorokin, A. M. Khenkin, S. A. Marakushev, A. E. Shilov, and A. A. Shteinman, Dokl. Akad. Nauk SSSR, 1984, 279, 939.

    Google Scholar 

  108. M. C. Feiters, A. E. Rowan, and R. J. M. Nolte, Chem. Soc. Rev., 2000, 29, 375.

    Google Scholar 

  109. O. N. Gritsenko, G. N. Nesterenko, V. S. Kulikova, and A. A. Shteinman, Kinet. Katal., 1997, 38, 699 [Kinet. Catal., 1997, 38, 639].

    Google Scholar 

  110. O. N. Gritsenko, G. N. Nesterenko, and A. A. Shteinman, Izv. Akad. Nauk, Ser. Khim., 1995, 2518 [Russ. Chem. Bull., 1995, 44, 2415 (Engl. Transl.)].

    Google Scholar 

  111. G. I. Panov, V. I. Sobolev, K. A. Dubkov, V. N. Parmon, N. S. Ovanesyan, A. E. Shilov, and A. A. Shteinman, React. Kinet. Catal. Lett., 1997, 61, 251.

    Google Scholar 

  112. J. T. Groves, M. Bonchio, N. Carofiglio, and K. Shalaev, J. Am. Chem. Soc., 1996, 118, 8961.

    Google Scholar 

  113. J. T. Groves and P. J. Viski, J. Am. Chem. Soc., 1989, 111, 8537.

    Google Scholar 

  114. K. Chen and L. Que, Jr., J. Chem. Soc., Chem. Commun., 1999, 1375.

  115. Y. Mekmouche, C. Duboc-Toia, S. Menage, C. Lambeaux, and M. Fontecave, J. Mol. Catal. (A), 2000, 156, 85.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shteinman, A.A. The role of metal-oxygen intermediates in biological and chemical monooxygenation of alkanes. Russian Chemical Bulletin 50, 1795–1810 (2001). https://doi.org/10.1023/A:1014321827168

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1014321827168

Navigation