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Biological Oxidations: Stereochemical Aspects

  • Chapter
Metalloporphyrins Catalyzed Oxidations

Part of the book series: Catalysis by Metal Complexes ((CMCO,volume 17))

Abstract

Correlation of the structure of enzymes with their catalytic activity is one of the most fundamental challenges of structural biology. Ultimately, the various features that characterize the action of enzymes may be understood at a molecular level. These include physical factors, i.e. how the substrates are bound, and chemical factors, i.e. the chemical mechanism of the enzymatic reaction. Our concern here is mostly with the first of these points, since all current evidence shows that binding of the substrates to the active site of heme proteins involved in biological oxidations is the main source of chemoselectivity associated with the enzyme catalyzed reactions, including stereoselectivity and enantioselectivity.

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References

  1. A.R. Fersht: Enzyme Structure and Mechanism, Chapter 12, W.H. Freeman, New York (1985).

    Google Scholar 

  2. D.D. Hackney: Enzymes 19, 1 (1990).

    CAS  Google Scholar 

  3. F.M. Menger: Biochemistry 31, 5368 (1992).

    CAS  Google Scholar 

  4. D.P. O’Keefe and P.A. Hard: Mof. 91Ticroóiol. 5, 2099 (1991).

    Google Scholar 

  5. I.C. Gunsalus, P.K. Bhattacharya and K. Suhara: Curr. Top. Cell. *gut. 26, 295 (1986).

    Google Scholar 

  6. F.P. Guengerich ed.: Mammalian Cytochromes P-450, CRC Press, Boca Raton, FL (1987).

    Google Scholar 

  7. J.-L. Riviere and F. Cabanne: Biochimie 69, 743 (1987).

    CAS  Google Scholar 

  8. S.D. Black and M.J. Coon: Adv. Enzymol. *lat. Areas Mol. Biol. 60, 35 (1987).

    CAS  Google Scholar 

  9. T. Andersson and L. Foerlin: Aquas. Toxicof. 24, 1 (1992).

    CAS  Google Scholar 

  10. R. Feyereisen, F.A. Carino and J.F. Koener: 9ev. Pectic. Toxicol. 1, 163 (1991).

    CAS  Google Scholar 

  11. D.R. Nelson et al.: DNA Cell Biol. 12, 1 (1993).

    CAS  Google Scholar 

  12. R.P. Donaldson and D.G. Luster: Plant Physiol. 96, 669 (1991).

    CAS  Google Scholar 

  13. F. Durst: Microbial and Plant Cytochrome P450: Biochemical Characteristics, Genetic Engineering and Practical Implications (eds. K. Ruckpaul and A. Rein), p. 191, Akademic Verlag, Berlin (1989).

    Google Scholar 

  14. F.P. Guengerich: FASBB5. 6, 745 (1992).

    CAS  Google Scholar 

  15. M.R. Waterman: Curr. Opin. Struct. Biot. 2, 384 (1992).

    CAS  Google Scholar 

  16. S.D. Black: FASBB5. 6, 680 (1992).

    CAS  Google Scholar 

  17. D.W. Nebert and D.R. Nelson: Methods Enzymot. 206, 3 (1991).

    CAS  Google Scholar 

  18. F.P. Guengerich and T.L. Macdonald: FASBB5. 4, 2453 (1990).

    CAS  Google Scholar 

  19. T.D. Porter and M.J. Coon: 5. Biot Chem- 266, 13469 (1991).

    CAS  Google Scholar 

  20. M.J. Coon, X. Ding, S. J. Pernecky and A.D.N. Vaz: FASBB 5. 6, 669 (1992).

    Google Scholar 

  21. F.P. Guengerich: Crit. 9çv. Biochem. Mot. Biat 25, 97 (1990).

    CAS  Google Scholar 

  22. P.R. Ortiz de Montellano:’Trends Pharn aco[. Sci. 10, 354 (1989).

    Google Scholar 

  23. F.P. Guengerich: 5. Blot. Chem. 266, 10019 (1991).

    Google Scholar 

  24. J.B. Schenkman: Molecular Aspects of Monooxygenases and Bioactivation of Toxic Compounds (eds. E. Arinç et al.), p. 1, Plenum Press, New York (1991).

    Google Scholar 

  25. T.L. Poulos, B.C. Finzel, I.C. Gunsalus, G.C. Wagner and J. Kraut: 5. Biot Chem. 260, 16122 (1985).

    CAS  Google Scholar 

  26. T.L. Poulos, B.C. Finzel and A. J. Howard: 5. 9v[ot Blot. 195, 687 (1987).

    CAS  Google Scholar 

  27. T.L. Poulos, B.C. Finzel and A.J. Howard: Biochemistry 25, 5314

    Google Scholar 

  28. R. Raag and T.L. Poulos: Bioche

    Google Scholar 

  29. R. Raag and T.L. Poulos: Biochemistry

    Google Scholar 

  30. R. Raag and T.L. Poulos: Biochemistry

    Google Scholar 

  31. R. Raag, S.A. Martinis, S.G. S.igar and T.L. Poulos: Biochemistry 30, 11420 (1991).

    CAS  Google Scholar 

  32. S.S. Boddupalli, C.A. Haseman, K.G. Ravichandran, J.Y. Lu, J.E. Goldsmith, J. Deisenhofer and J.A. Peterson: Proc. Natl. Acad. Sci. USA 89, 5567 (1992).

    CAS  Google Scholar 

  33. R.T. Reuttinger, L.-P. Wen and A.J. Fulco: 5. Blot. Chem. 264, 10987 (1989).

    Google Scholar 

  34. P.S. Stayton and S.G. Sligar: Biochemistry29, 7381 (1990).

    Google Scholar 

  35. P.S. Stayton, T.L. Poulos and S.G. Sugar: Biochemistry 28, 8201 (1989).

    CAS  Google Scholar 

  36. W.M. Atkins and S.G. Sligar: 5. Biot Chem. 263, 18842 (1988).

    CAS  Google Scholar 

  37. W.M. Atkins and S.G. Sligar: 5. Am. Chem. Soc. 111, 2715 (1989).

    CAS  Google Scholar 

  38. C. Di Primo, G. Hui Bon Hoa, P. Douzou and S.G. Sugar: 5. Biot. Chem. 265, 5361 (1990).

    Google Scholar 

  39. M. Imai, H. Shimada, Y. Watanabe, Y. Matsushima-Hibiya, R. Makino, H. Koga, T. Horiuchi and Y. Ishimura: Proc. Wat. Asad Sci. USA 86, 7823 (1989).

    CAS  Google Scholar 

  40. S.A. Martinis, W.M. Atkins, P.S. Stayton and S.G. Sugar: 5. Am. Chem. Soc. 111, 9252 (1989).

    CAS  Google Scholar 

  41. H. Shimada, Y. Watanabe, M. Imai, R. Makino, H. Koga, T. Horiuchi and Y. Ishimura: Dioxygen Activation and Homogeneous Catalytic Oxidation (ed. L.I. Simandi), p. 313, Elsevier, Amsterdam (1991).

    Google Scholar 

  42. T.L. Poulos and R. Raag: FASEB5. 6, 674 (1992).

    Google Scholar 

  43. N.C. Gerber and S.G. Sligar: 5. Am. Chem. Soc. 114, 8742 (1992).

    CAS  Google Scholar 

  44. P.R. Ortiz de Montellano, J.A. Fruetel, J.R. Collins, D.L. Camper and G.H. Loew: 5. Am. Chem. Soc. 113, 3195 (1991).

    Google Scholar 

  45. J.A. Fruetel, J.R. Collins, D.L. Camper, G.H. Loew and P.R. Ortiz de Montellano: 5.54m. Chem. Soc. 114, 6987 (1992).

    CAS  Google Scholar 

  46. Y. Watanabe and Y. Ishimura: 5. Am. Chem. Soc. 111, 410 (1989).

    CAS  Google Scholar 

  47. B. Filipovic, M.D. Paulsen, P.J. Loida, S.G. Sligar and R.L. Ornstein: Biochem. Biophys. 9s. Commun. 189, 488 (1992).

    CAS  Google Scholar 

  48. J.P. Jones, W.F. Trager and T.J. Carlson: 5. Am. Chem. Soc. 115, 381 (1993).

    CAS  Google Scholar 

  49. W.M. Atkins and S.G. Sligar: 5. Am. Chem. Soc. 109, 3754 (1987).

    CAS  Google Scholar 

  50. M.D. Paulsen and R.L. Ornstein: Abstract 283, 8th International Symposium on Microsomes and Drug Oxidations, Stockholm, Sweden, June 25–29 (1990).

    Google Scholar 

  51. P.A. Cole and C.H. Robinson: 5. Med Chem. 33, 2933 (1990).

    CAS  Google Scholar 

  52. T.L. Poulos: Methods Bnzymot 206, 11 (1991).

    CAS  Google Scholar 

  53. D.R. Nelson and H.W. Strobel: 5. Bio(. Chem. 263, 6038 (1988).

    CAS  Google Scholar 

  54. D.R. Nelson and H.W. Strobel: Biochemistry 28, 656 (1989).

    CAS  Google Scholar 

  55. V.E. Tretiakov, K.N. Degtyarenko, V.Y. Uvarov and A.I. Archakov: Arch. Biochem. Biophys. 275, 429 (1989).

    CAS  Google Scholar 

  56. M.J.J.M. Zvelebil, C.R. Wolf and M. J.E. Sternberg: Protein Eng. 4, 271 (1991).

    CAS  Google Scholar 

  57. C.A. Laughton, S. Neidle, M.J.J.M. Zvelebil and M.J.E. Sternberg: Biochem. Biophys. Xçs. Commun. 171, 1160 (1990).

    CAS  Google Scholar 

  58. D.F.V. Lewis and H. Moereels: 5. Comput.-Aided Mo(. Design 6, 235 (1992).

    CAS  Google Scholar 

  59. C.A. Ouzounis and W.T. Melvin: Eur. 5. Biochem. 198, 307 (1991).

    CAS  Google Scholar 

  60. O. Gotoh: 5. Biol. Chem. 267, 83 (1992).

    Google Scholar 

  61. E.F. Johnson: Trends Pharmaco(. Sci. 13, 122 (1992).

    CAS  Google Scholar 

  62. E.F. Johnson, T. Kronbach and M.-H. Hsu: FASEB5. 6, 700 (1992).

    CAS  Google Scholar 

  63. T. Omura and A. Ito: Methods Enzymot 206, 75 (1991).

    CAS  Google Scholar 

  64. T. Kronbach, B. Kemper and E.F. Johnson: Biochemistry 30, 6097 (1991).

    CAS  Google Scholar 

  65. K.M. Kedzie et al.: 5. Biot. Chem. 266, 22515 (1991).

    Google Scholar 

  66. Y.-A. He, C.A. Balfour, K.M. K.dzie and J.R. Halpert: Biochemistry 31, 9220 (1992).

    CAS  Google Scholar 

  67. R.O. Juvonen, M. Iwasaki and M. Negishi: 5. Biol. Chem. 266, 16431 (1991).

    CAS  Google Scholar 

  68. R.L.P. Lindberg and M. Negishi: Nature (London)339, 632 (1989).

    Google Scholar 

  69. R. Lindberg, B. Burkhart, T. Ichikawa and M. Negishi: 5. Biot Chem. 264, 6465 (1989).

    CAS  Google Scholar 

  70. M. Ishigooka, T. Shimizu, K. Hiroya and M. Hatano: Biochemistry 31, 1528 (1992).

    CAS  Google Scholar 

  71. T. Shimizu, A.J.M. Sadeque, G.N. Sadeque, M. Hatano and Y. FujiiKuriyama: Biochemistry 30, 1490 (1991).

    CAS  Google Scholar 

  72. T. Shimizu, O. Ito, M. Hatano and Y. Fujii-Kuriyama: Biochemistry 30, 4659 (1991).

    CAS  Google Scholar 

  73. A.G. Krainev, T. Shimizu, M. Ishigooka, K. Hiroya, M. Hatano and Y. Fujii-Kuriyama: Biochemistry 30, 11206 (1991).

    CAS  Google Scholar 

  74. M. Delaforge, P. Battioni, J.P. Mahy and D. Mansuy: Chem. -Biot. Interact. 60, 101 (1986).

    CAS  Google Scholar 

  75. D. Ringe, G.A. Petsko, D.E. Kerr and P. R. Ortiz de Montellano: Biochemistry 23, 2 (1984).

    CAS  Google Scholar 

  76. P. Raag, B.A. Swanson, T.L. Poulos and P.R. Ortiz de Montellano: Biochemistry 29, 8119 (1990).

    CAS  Google Scholar 

  77. B.A. Swanson and P.R. Ortiz de Montellano: 5. Am. Chem. Soc. 113, 8146 (1991).

    CAS  Google Scholar 

  78. B.A. Swanson, D.R. Dutton, J.M. Lunatta, C.S. Yang and P.R. Ortiz de Montellano: 5. Biot. Chem. 266, 19258 (1991).

    CAS  Google Scholar 

  79. B.A. Swanson, J.R. Halpert, L.M. Bornheim and P.R. Ortiz de Montellano: Arch. Biochem. Biophys. 292, 42 (1992).

    CAS  Google Scholar 

  80. S.F. Tuck, J.A. Peterson and P.R. Ortiz de Montellano: 5. Biot. Chem. 267, 5614 (1992).

    CAS  Google Scholar 

  81. P.R. Ortiz de Montellano, W.K. Chan, S.F. Tuck, R.M. Kaikaus, N.M. Bass and J.A. Peterson: FASBB5. 6, 695 (1992).

    Google Scholar 

  82. S.F. Tuck, S. Graham-Lorence, J.A. Peterson and P.R. Ortiz de Montellano: 5. Biot. Chem. 268, 269 (1993).

    CAS  Google Scholar 

  83. S.F. Tuck and P.R. Ortiz de Montellano: Biochemistry 31, 6911 (1992).

    CAS  Google Scholar 

  84. M. Murray and F. Reidy: Pharmacof. Xgv. 42, 85 (1990).

    CAS  Google Scholar 

  85. L. E. Vickery: Methods Enzymot. 206, 548 (1991).

    CAS  Google Scholar 

  86. D.V. Parke, C. Ioannides and D.F.V. Lewis: Can. 5. Physiof. Pharmacof. 69, 537 (1991).

    CAS  Google Scholar 

  87. a) L. Koymans et al.: Chem. *s. Toxicot. 5, 211 (1992). (b) D.A. Smith and B.C. Jones: Biochem. Pharmacot 44, 2089 (1992).

    Google Scholar 

  88. L. Castro-Maderal and P.D. Sullivan: EBBS Lett. 296, 249 (1992).

    CAS  Google Scholar 

  89. D.R. Boyd, C.T. Walsh and Y.C.J. Chen: Sulfur Containing Drugs and Related Compounds (ed. L.A. Damani), p. 67, Ellis Horwood Ltd., Chichester, U.K. (1989).

    Google Scholar 

  90. T. Tanaka, M. Yamasaki, K. Fujimori, Y.H. Kim and S. Oae: Bull. Chem. Soc. Spn. 56, 2300 (1983).

    Google Scholar 

  91. S. Oae, A. Mikami, T. Matsuura, K. Ogawa-Asada, Y. Watanabe, K. Fujimori and T. Iyanagi: Biochen. Biophys. *s. Commun. 131, 567 (1985).

    CAS  Google Scholar 

  92. G. Modena and L. Maioli: azz. Chini. Ital. 87, 1306 (1957).

    CAS  Google Scholar 

  93. K. Fujimori, T. Matsuura, A. Mikami, Y. Watanabe and S. Oae: 5. Chem. Soc. Perlin I’Trans., 1435 (1990).

    Google Scholar 

  94. J.R. Cashman, L.D. Olsen and L. Borheim: Chem. cs. Toxicot 3, 344 (1990).

    CAS  Google Scholar 

  95. J.R. Cashman, L.D. Olsen and L.M. Borheim: 5. 91m. Chem. Soc. 112, 3191 (1990).

    CAS  Google Scholar 

  96. J.R. Cashman and L.D. Olsen: Mo! Pharmacy!. 38, 573 (1991).

    Google Scholar 

  97. J.R. Cashman, L.D. Olsen, D.R. Boyd, R. Austin, S. McMordie, R. Dunlop, and H. Dalton: 5. dim. Chem. Soc. 114, 8772 (1992).

    Google Scholar 

  98. J.C. Alvarez and P.R. Ortiz de Montellano: Biochemistry 31, 8315 (1992).

    CAS  Google Scholar 

  99. P.R. Ortiz de Montellano: Cytochrome P-450: Structure, Mechanism, and Biochemistry (ed. P.R. Ortiz de Montellano), p. 217, Plenum Press, New York (1986).

    Google Scholar 

  100. M.J. Gunter and P. Turner: Coord. Chem. 14v. 108, 115 (1991).

    Google Scholar 

  101. D. Ostovic and T.C. Bruice:. Bruice: Acc. Chem. 14.5. 25, 314 (1992).

    Google Scholar 

  102. D. Wistuba, H.P. Nowotny, O. Träger and V. Schurig: Chiratity 1, 127 (1989).

    CAS  Google Scholar 

  103. S.K. Yang: Biochem. Pharmacot. 37, 61 (1988).

    CAS  Google Scholar 

  104. S.K. Yang, M. Mushtaq, H.B. Weems, D.W. Miller and P.P. Fu: Biochem. 9. 245, 191 (1987).

    Google Scholar 

  105. G.K.B. Prasad and D.R. Thakker: Biochem. Biophys. Jas. Commun. 181, 1516 (1991).

    CAS  Google Scholar 

  106. J.H. Capdevila, J.R. Falck and R.W. Estabrook: MEW 5. 6, 731 (1992).

    Google Scholar 

  107. J.H. Capdevila, A. Karara, D.J. Waxman, M.V. Martin, J.R. Falck and F.P.Guengerich: 5. Bid. Chem. 265, 10865 (1990).

    CAS  Google Scholar 

  108. F.A. Fitzpatrick and R.C. Murphy: Pharmacot. Rçv. 40, 229 (1989).

    Google Scholar 

  109. A. Karara, E. Dishman, H. Jacobson, J.R. Falck and J.H. Capdevila: 5PBS Lett. 268, 227 (1990).

    CAS  Google Scholar 

  110. R.M. Laethem, C.L. Laethem and D.R. Koop: 5. Biot. Chem. 267, 5552 (1992).

    CAS  Google Scholar 

  111. H. Tyson: ‘Aeon. pp(. Genet. 84, 643 (1992).

    Google Scholar 

  112. K.G. Welinder: Curr. Opin. Struct. Biot. 2, 388 (1992).

    CAS  Google Scholar 

  113. J. Lobarzewski, H. Greppin, C. Penel and T. Gaspar (eds.): Biochemical, Molecular and Physiological Aspects of Plant Peroxidases, University of Geneva, Geneva (1991).

    Google Scholar 

  114. J. Everse, K.E. Everse and M.B. Grisham: Peroxidases in Chemistry and Biology, CRC Press, Boca Raton (1991).

    Google Scholar 

  115. M. Stiborova, E. Frei, H.H. Schmeister and P. Anzenbacher: Drug Meta6. Drug Interact. 9, 177 (1991).

    CAS  Google Scholar 

  116. P.F. Hollenberg: FASEB 5. 6, 686 (1992).

    Google Scholar 

  117. H.B. Dunford: See ref. 114, Vol. 2, p. 1.

    Google Scholar 

  118. B.C. Finzel, T.L. Poulos and J. Kraut: 5. Biot. Chem. 259, 13027 (1984).

    CAS  Google Scholar 

  119. H.R. Bosshard, H. Anni and T. Yonetani: See ref. 114, Vol. 2, p. 51.

    Google Scholar 

  120. J.H. Dawson: Science 240, 433 (1988).

    CAS  Google Scholar 

  121. T.L. Poulos: Adv. Inorg. Biocheni. 7, 1 (1988).

    CAS  Google Scholar 

  122. H. Anni and T. Yonetani: stet. Ions Biot. Syst. 28, 219 (1992).

    CAS  Google Scholar 

  123. P.R. Ortiz de Montellano: Annu. Rev. Pharmacot Taxicof. 32, 89 (1992).

    Google Scholar 

  124. S.L. Edwards, H.X. Xuong, R.C. Hamlin and J. Kraut: Biochemistry 26, 1503 (1987).

    CAS  Google Scholar 

  125. M. Sivaraja, D.B. Goodin, A.G. Mauk, M. Smith and B.A. Hoffman: Science 245, 738 (1989).

    CAS  Google Scholar 

  126. L.B. Vitello, J.E. Erman, J.M. Mauro and J. Kraut: Biochim. Biophys. Acta 1038, 90 (1990).

    CAS  Google Scholar 

  127. D.K. Bhattacharyya, IJ. Bandyopadhyay and R.K. Banerjee: 5. Biot Chem. 267, 9800 (1992).

    CAS  Google Scholar 

  128. L.J. Marnett: Biological Oxidation Systems, Vol. 2, p. 637, Academic Press, New York (1990).

    Google Scholar 

  129. Y. Morita, B. Mikami, H. Yamashita, J.Y. Lee, S. Aibara, M. Sato, Y. Katsube and N. Tanaka: See ref. 113, p. 81.

    Google Scholar 

  130. S.L. Edwards, R. Raag, H. Wariishi, M.H. Gold and T.L. Poulos: Proc. watt. Acad. Sci. USA 90, 750 (1993).

    CAS  Google Scholar 

  131. J. Zeng and R.E. Fenna: 5. Mot. Biot. 226, 185 (1992).

    CAS  Google Scholar 

  132. J.D. Satterlee, J.E. Erman, J.M. Mauro and J. Kraut: Biochemistry 29, 8797 (1990).

    CAS  Google Scholar 

  133. J.E. Erman, L.B. Vitello, M.A. Miller and J. Kraut: 5. Am. Chem. Soc. 114, 6592 (1992).

    CAS  Google Scholar 

  134. I. Fita and M.G. Rossman: 5. Mot. Biot. 185, 21 (1985).

    CAS  Google Scholar 

  135. K. Choudhury, M. Sundaramoorthy, J.M. Mauro and T.L. Poulos: 5. Biol. Chem. 267, 25656 (1992).

    CAS  Google Scholar 

  136. M.A. Ator and P.R. Ortiz de Montellano: 5. Biot. Chem. 262, 1542 (1987).

    CAS  Google Scholar 

  137. G.D. DePillis, H. Wariishi, M.H. Gold and P.R. Ortiz de Montellano: Arch. Biochem. Biophys. 280, 217 (1990).

    CAS  Google Scholar 

  138. R.Z. Harris, H. Wariishi, M.H. Gold and P.R. Ortiz de Montellano: 5. Biot. Chem. 266, 8751 (1991).

    CAS  Google Scholar 

  139. G. DePillis and P.R. Ortiz de Montellano: Biochemistry 28, 7947 (1989).

    CAS  Google Scholar 

  140. I. Morishima and S. Ogawa: 5. Biol. Chem. 254, 2814 (1979).

    CAS  Google Scholar 

  141. J. Sakurada, S. Takahashi and T. Hosoya: 5. Biot. Chem. 261, 9657 (1986).

    CAS  Google Scholar 

  142. S. Modi, D.V. Behere and S. Mitra: Biochim. Biophys. Acta 996, 214 (1989).

    CAS  Google Scholar 

  143. L. Casella, M. Gullotti, S. Poli, M. Bonfà, R.P. Ferrari and A. Marchesini: Biochem. 5. 279, 245 (1991).

    Google Scholar 

  144. N.C. Veitch and R.J.P. Williams: Ear. 5. Biochem. 189, 351 (1990).

    CAS  Google Scholar 

  145. N.C. Veitch and R.J.P. Williams: See ref. 113, p. 99.

    Google Scholar 

  146. G.N. LaMar, G. Hernanàndez and J.S. de Ropp: Biochemistry 31, 9158 (1992).

    CAS  Google Scholar 

  147. L. Banci, I. Bertini,T. Bini, M. Tien and P. Turano: Submitted for publication.

    Google Scholar 

  148. A.T. Smith, S.A. Sanders, R.N.F. Thorneley, J.F. Burke and R.C. Bray: Bur. 5. Biochem. 207, 507 (1992).

    CAS  Google Scholar 

  149. N.C. Veitch, R.J.P. Williams, R.C. Bray, J.F. Burke, S.A. Sanders, R.N.F. Thorneley and A.T. Smith: Bur. 5. Biochem. 207, 521 (1992).

    CAS  Google Scholar 

  150. A. Corin, G. McLendon, Q. Zhang, R. Hake, J. Falvo, K. Lu, R. Ciccarelli and D. Holzschu: Biochemistry 30, 11585 (1991).

    CAS  Google Scholar 

  151. H. Pelletier and J. Kraut: Science 258, 1748 (1992).

    CAS  Google Scholar 

  152. R. Hake, G. McLendon, A. Corin and D. Holzschu: 5. in. Chem. Soc. 114, 5442 (1992).

    CAS  Google Scholar 

  153. G.D. DePillis, B.P. Sishta, A.G. Mauk and P.R. Ortiz de Montellano: 5. Bio(. Chem. 266, 19334 (1991).

    CAS  Google Scholar 

  154. V.P. Miller, G.D. DePillis, J.C. Ferrer, A.G. Mauk and P.R. Ortiz de Montellano: 5. Biot. Chem. 267, 8936 (1992).

    CAS  Google Scholar 

  155. L. Casella, M. Gullotti, S. Poli and E. Santelli: To be submitted for publication.

    Google Scholar 

  156. E.L. Thomas, P.M. Bozeman and D.B. Learn: See ref. 114, Vol. 1, p. 123.

    Google Scholar 

  157. G.S. Bayse, A.W. Michaels and M. Morrison: Biochim. Biophys.Acta 284, 34 (1972).

    CAS  Google Scholar 

  158. S. Colonna, N. Gaggero, G. Carrea and P. Pasta: 5. Chem. Soc. Chem. Commun., 357 (1992).

    Google Scholar 

  159. R. Z. Harris, S.L. Newmyer and P.R. Ortiz de Montellano: 5. Biot. Chem. 268, 1637 (1993).

    CAS  Google Scholar 

  160. E. Blée and F. Schuber: Biochemistry 28, 4962 (1989).

    Google Scholar 

  161. W.L. Smith, T.E. Eling, R.J. Kulmacz, L. J. Marnett and A. Tsai: Biochemistry 31, 3 (1992).

    Google Scholar 

  162. P. Plé and L.J. Marnett: 5. Bid. Chem. 264, 13983 (1989).

    Google Scholar 

  163. L. Casella, M. Gullotti, R. Ghezzi, S. Poli, T. Beringhelli, S. Colonna and G. Carrea: Biochemistry 31, 9451 (1992).

    CAS  Google Scholar 

  164. U. Pérez and H.B. Dunford: Biochim. Biophys. eta 1038, 98 (1990).

    Google Scholar 

  165. U. Pérez and H.B. Dunford: Biochemistry 29, 2757 (1990).

    Google Scholar 

  166. P.R. Ortiz de Montellano, Y.S. Choe, G. DePillis and C.E. Catalano: 5. Biot. Chem. 262, 11641 (1987).

    Google Scholar 

  167. A.A. Elfarra, R.J. Duescher and C.M. Pasch: Arch. Biochem. Biophys. 286, 244 (1991).

    CAS  Google Scholar 

  168. D.R. Doerge, N.M. Cooray and M. E. Brewster: Biochemistry 30, 8960 (1991).

    CAS  Google Scholar 

  169. S. Kobayashi, M. Nakano, T. Goto, T. Kimura and A.P. Schaap: Biochim. Biophys. 94s. Commun. 135, 166 (1986).

    CAS  Google Scholar 

  170. R.J. Duescher and A.A. Elfarra: 9. Biot. Chem. 267, 19859 (1992).

    CAS  Google Scholar 

  171. W.D. Hewson and L.P. Hager: The Porphyrins (ed. D. Dolphin), Vol. VII, Part B, p. 295, Academic Press, New York (1979).

    Google Scholar 

  172. B.W. Griffin: See ref. 114, Vol. 2, p. 85.

    Google Scholar 

  173. S.R. Blanke and L.P. Hager: J. Biot. Chem. 263, 18739 (1988).

    CAS  Google Scholar 

  174. S.R. Blanke and L.P. Hager: 5. Biot. Chem. 265, 12454 (1990).

    CAS  Google Scholar 

  175. L.B. Dugad, X. Wang, C.-C. Wang, G.S. Lukat and H.M. Goff: Biochemistry 31, 1651 (1992).

    CAS  Google Scholar 

  176. V.M. Samokyszyn and P.R. Ortiz de Montellano: Biochemistry 30, 11646 (1991).

    CAS  Google Scholar 

  177. L. Casella, M. Gullotti, C. Selvaggini, S. Poli and T. Beringhelli: Submitted for publication.

    Google Scholar 

  178. D.R. Doerge and M.D. Corbett: Chen rs. Toxrcol. 4, 556 (1991).

    CAS  Google Scholar 

  179. A.-M. Lambeir, H.B. Dunford and M.A. Pickard: Bur. 9. Biochem. 163, 123 (1987).

    CAS  Google Scholar 

  180. S. Colonna, N. Gaggero, A. Manfredi, L. Casella, M. Gullotti, G. Carrea and P. Pasta: Biochemistry 29, 10466 (1990).

    Google Scholar 

  181. S. Colonna, N. Gaggero, L. Casella, G. Carrea and P. Pasta: Tetrahedron,Asymmetry 3, 95 (1992).

    CAS  Google Scholar 

  182. H. Fu, H. Kondo, Y. Ichikawa, G.C. Cook and C.H. Wong: y. Org. Chem. 57, 7265 (1992).

    CAS  Google Scholar 

  183. M.B. McCarthy and R.E. White: 9. Bio! Chem. 258, 9153 (1983).

    CAS  Google Scholar 

  184. J. Geigert, T.D. Lee, D.J. Dalietos, D.S. Hirano and S.L. Neidleman: Biochem. Biophys. *s. Commun. 136, 778 (1986).

    CAS  Google Scholar 

  185. A.A. Elfarra, R.J. Duescher and C.M. Pasch: Arch. Biochem. Biophys. 286, 244 (1991).

    CAS  Google Scholar 

  186. S. Colonna, N. Gaggero, L. Casella, G. Carrea and P. Pasta: Tetrahedron Asymmetry 4, 1325 (1993).

    CAS  Google Scholar 

  187. C.-H. Wong: Science 244, 1145 (1989).

    CAS  Google Scholar 

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Casella, L., Colonna, S. (1994). Biological Oxidations: Stereochemical Aspects. In: Montanari, F., Casella, L. (eds) Metalloporphyrins Catalyzed Oxidations. Catalysis by Metal Complexes, vol 17. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-2247-6_10

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