Selective oxidations catalyzed by peroxidases

Tetrahedron

Volumn 53, Issue 39, 1997, Pages 13183-13220

  Van Deurzen, Marion P J ^a,b   Van Rantwijk, Fred ^a   Sheldon, Roger A ^a  

^a DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b UNILEVER RESEARCH VLAARDINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; AMINO ACID; ANTIBIOTIC AGENT; CHLORIDE PEROXIDASE; CYTOCHROME C PEROXIDASE; CYTOCHROME P450; DILTIAZEM; HYDRAZINE DERIVATIVE; HYDROGEN PEROXIDE; PEROXIDASE; SULFIDE; SULFOXIDE;

CATALYSIS; CHEMICAL MODIFICATION; ELECTRON TRANSPORT; ENZYME MECHANISM; EPOXIDATION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW;

EID: 0030750870     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00477-8     Document Type: Review

References (216)

1. Wichmann, R.; Wandrey, C.; Leuchtenberger, W.; Kula, M.R. and Bückmann, A.F. (Degussa; Gesellschaft für Biotechnologische Forschung) Ger. Offen. DE 2930087 [Chem. Abstr. 1981, 94, 172901].
2. Peroxidases in Chemistry and Biology, Vol. I and II; Everse, J.; Everse; K.E. and Grisham, M.B. Eds.; CRC Press: Boca Raton, 1991.
3. Plant Peroxidases in Biochemistry and Physiology; Welinder, K.G.; Rasmussen, S.K.; Penel, C. and Greppin, H. Eds.; University of Geneva: Geneva, 1993.
4. Saunders, B.C.; Holmes Siedle, A.G. and Stark, B.P. Peroxidase; Buttersworths: Washington, 1964.
5. Dunford, H.B. Adv. Inorg. Biochem., 1982, 4, 41-68.
6. Hewson, W.D. and Hager, L.P. in The Porphyrins Vol. 7B; Dolphin, D. Ed.; Academic Press: New York, 1979; pp. 295-332.
7. Neidleman, S.L. and Geigert, J. Biohalogenation, Principles, Basic roles and Applications; Ellis Horwood Ltd.; Chicester: 1986.
8. Franssen, M.C.R. and van der Plas, H.C. Adv. Appl. Microbiol. 1992, 37, 41-98.
9. Franssen, M.C.R. Biocatalysis 1994, 10, 87-112.
10. Gallagher, P.H. Biochem. J. 1923, 17, 515-529.
11. Fukunishi, K.; Kitada, K. and Naito, I. Synthesis 1991, 237-238.
12. Zemel, H. and Quinn, J.F. (Allied Signal Inc.) PCT Int. Appl. WO 94 10327 [Chem. Abstr. 1994, 121, 177877]; Chem. Eng. News April 19, 1993, 71, 36-37.
13. Zemel, H. and Quinn, J.F. (Allied Signal Inc.) PCT Int. Appl. WO 94 10327 [Chem. Abstr. 1994, 121, 177877]; Chem. Eng. News April 19, 1993, 71, 36-37.
14. Dordick, J.S. Tibtech. 1992, 10, 287-293.
15. Uyama, H.; Kurioka, H.; Sugihara J. and Kobayashi, S. Bull. Chem. Soc. Jap. 1996, 69, 189-193.
16. Kobayashi, S.; Shoda, S. and Uyama, H. Adv. Pol. Sci. 1995, 121, 1-30.
17. Meunier, B. in Peroxidases in Chemistry and Biology, Vol. II; Everse, J.; Everse, K.E. and Grisham, M.B. Eds.; CRC Press: Boca Raton, 1991; pp. 201-217.
18. Meunier, G. and Meunier, B. J. Am Chem. Soc. 1985, 107, 2558-2560.
19. Shaw, P.D. and Hager, L.P. J. Biol. Chem. 1961, 236, 1626-1630.
20. Morris, D.R. and Hager, L.P. J. Biol. Chem. 1966, 241, 1763-1768.
21. Wiesner, W.; van Pée, K.-H. and Lingens, F. FEBS Lett. 1986, 209, 321-324.
22. Arnao, M.B.; Acosta, M.; del Río, M.A.; Varón, R. and García-Cánovas, F. Biochim. Biophys. Acta 1990, 1041, 43-47.
23. Sun, W.; Kadima, T.A.; Pickard, M.A. and Dunford, H.B. Biochem. Cell. Biol. 1994, 72, 321-331.
24. Kanofsky, J.R. J. Biol. Chem. 1984, 259, 5596-5600.
25. Everett, R.R. and Butler, A. Inorg. Chem. 1989, 28, 393-395.
26. Hochman, A. in Plant Peroxidases in Biochemistry and Physiology; Welinder, K.G.; Rasmussen, S.K.; Penel, C. and Greppin, H. Eds.; University of Geneva: Geneva, 1993; pp. 103-112.
27. Barbachyn, M.R. and Johnson, C.R. in Asymmetric Synthesis; Morrison, J.D. Ed.; Academic Press: New York, 1988; p. 233.
28. Carreño, M.C. Chem. Rev. 1995, 95, 1717-1760.
29. Andersen, K.K. Tetrahedron Lett. 1962, 3, 93-95.
30. Noda, K.; Hosoya, N.; Irie, R.; Yamashita, Y. and Katsuki, T. Tetrahedron, 1990, 50, 9609-9618.
31. Holland, H.L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992; pp. 255-311.
32. Kagan, H.B. in Catalytic Asymmetric Synthesis, Ojima, I. Ed.; VCH: New York, 1993; pp. 203-226.
33. Dabrowicz, J.; Kielbasinski, P. and Mikolajczyk, M. in The Chemistry of Sulphones and Sulphoxides; Patai, S.; Rappoport, Z. and Stirling, C.J.M. Eds.; Wiley: Chicester, 1988; pp. 233-378.
34. Doerge, D.R. Arch. Biochem. Biophys. 1986, 244, 678-685.
35. Doerge, D.R.; Cooray, N.M. and Brewster, M.E. Biochem. 1991, 30, 8960-8964.
36. Kobayashi, S.; Nakano, M.; Goto, T.; Kimura, T. and Schaap, A.P. Biochem. Biophys. Res. Commun. 1986, 135, 166-171.
37. Blée, E. and Durst, F. Arch. Biochem. Biophys. 1987, 254, 43-52.
38. Kobayashi, S.; Nakano, M.; Kimura, T. and Schaap, A.P. Biochem. 1987, 26, 5019-5022.
39. Colonna, S.; Gaggero, N.; Manfredi, A.; Casella, L.; Gullotti, M.; Carrea, G. and Pasta, P. Biochem. 1990, 29, 10465-10468.
40. Colonna, S.; Gaggero, N.; Casella, L.; Carrea, G. and Pasta, P. Tetrahedron: Asymm. 1992, 3, 95-106.
41. van Deurzen, M.P.J.; Remkes, I.J.; van Rantwijk, F. and Sheldon, R.A. J. Mol. Cat. A: Chemical in press.
42. Pasta, P.; Carrea, G.; Colonna, S. and Gaggero, N. Biochim. Biophys. Acta, 1994, 1209, 203-208.
43. Fu, H.; Kondo, H.; Ichikawa, Y.; Look, G.C. and Wong, C.-H. J. Org. Chem. 1992, 57, 7265-7270.
44. Geigert, J.; DeWitt, S.K.; Neidelman, S.L.; Lee, G.; Dalietos, D.J. and Moreland, M. Biochem. Biophys Res. Commun. 1983, 116, 82-85.
45. Colonna, S.; Gaggero, N.; Carrea, G. and Pasta, P. J. Chem. Soc., Chem. Commun. 1992, 357-358.
46. Harris, R.Z.; Newmyer, S.L. and Ortiz de Montellano, P.R. J. Biol. Chem. 1993, 268, 1637-1645.
47. Casella, L.; Gullotti, M.G.; Ghezzi, R.; Poli, S.; Beringhelli, T.; Colonna, S. and Carrea, G. Biochem. 1992, 31, 9451-9459.
48. Miller, V.P.; DePillis, G.D.; Ferrer, J.C.; Mauk, A.G. and Ortiz de Montellano, P.R. J. Biol. Chem. 1992, 267, 8936-8942.
49. Colonna, S.; Gaggero, N.; Carrea, G. and Pasta, P. Tetrahedron Lett. 1994, 35, 9103-9104.
50. Colonna, S.; Gaggero, N.; Richelmi, C.; Carrea, G. and Pasta, P. Gaz. Chim. Ital. 1995, 125, 479-482.
51. Ozaki, S. and Ortiz de Montellano, P.R. J. Am. Chem. Soc. 1994, 116, 4487-4488.
52. Newmyer, S.L. and Ortiz de Montellano, P.R. J. Biol. Chem. 1995, 270, 19430-19438.
53. Ozaki S. and Ortiz de Montellano, P.R. J. Am. Chem. Soc. 1995, 117, 7056-7064.
54. Blée, E. and Schuber, F. Biochem. 1989, 28, 4962-4967.
55. Corbett, M.D.; Chipko, B.R.and Baden, D.G. Biochem. J. 1978, 175, 353-360.
56. Corbett, M.D.; Baden, D.G. and Chipko, B.R. Bioorg. Chem. 1979, 8, 91-95.
57. Corbett, M.D.; Chipko, B.R. and Batchelor, A.O. Biochem J. 1980, 187, 893-903.
58. Corbett, M.D. and Corbett, B.R. Biochem, Arch. 1985, 1, 115-120.
59. Doerge, D.R. and Corbett, M.D. Chem. Res.Toxicol. 1991, 4, 556-560.
60. Ishimaru, A. and Yamazaki, I. J. Biol. Chem. 1977, 252, 6118-6124.
61. Corbett, M.D. and Corbett, B.R. J. Agric. Food Chem. 1983, 31, 1276-1282.
62. Holland, V.R. and Saunders, B.C. Tetrahedron 1968, 24, 585-588.
63. Kalliney, S. and Zaks, A. Tetrahedron Lett. 1995, 36, 4163-4166.
64. Itoh, N.; Morinaga, N. and Kouzai, T. Biochem. Mol. Biol. Int. 1993, 29, 785-791.
65. Kirner, S. and van Pée, K.-H. Angew. Chem., Int. Ed Engl. 1994, 33, 352-353.
66. Burd, W.; Yourkevich, O.; Voskoboev, A.J. and van Pée, K.-H. FEMS Microbiol. Lett. 1995, 129, 255-260.
67. Gorzynski Smith, J. Synthesis, 1984, 8, 629-656.
68. Davies, I.W. and Reider, P.J. Chem. Ind. 1996, 412-415.
69. Sheldon, R.A. Chirotechnology: Industrial Synthesis of Optically Active Compounds; Marcel Dekker Inc.: New York, 1993; pp. 371-374.
70. Besse, P. and Veschambre, H. Tetrahedron 1994, 50, 8885-8927.
71. Collman, J.P.; Zhang, X.; Lee, V.J.; Uffelman, E.S. and Brauman, J.I. Science 1993, 261, 1404-1411.
72. Jacobsen, E.N. in Catalytic Asymmetric Synthesis; Ojima, I. Ed.; VCH: New York, 1993; pp. 159-202.
73. Holland H.L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992; pp. 153-182.
74. Koch, A.; Reymond, J.L. and Lerner, R.A. J. Am. Chem. Soc. 1994, 116, 803-804.
75. Neidleman, S.L.; Amon W.F., Jr. and Geigert, J. (Cetus Corp.) US 4284723 [Chem. Abstr. 1981, 95, 167173].
76. Ortiz de Montellano, P.R. and Grab, L.A. Mol. Pharmacol. 1986, 30, 666-669.
77. Ortiz de Montellano, P.R. and Grab, L.A. Biochem. 1987, 26, 5310-5314.
78. Berkessel, A. lecture at the 6th international symposium on the activation of dioxygen and homogeneous catalytic oxidation, Noordwijkerhout, The Netherlands, April 17, 1996.
79. McCarthy, M.B. and White, R.E. J. Biol. Chem. 1983, 258, 9153-9158.
80. Geigert, J.; Lee, T.D.; Dalietos, D.J.; Hirano, D.S. and Neidleman, S.L. Biochem. Biophys. Res. Commun. 1986, 136, 778-782.
81. Ortiz de Montellano, P.R.; Choe, Y.S.; DePillis, G. and Catalano, C.E. J. Biol. Chem. 1987, 262, 11641-11646.
82. Elfarra, A.A.; Duescher, R.J. and Pasch, C.M. Arch. Biochem. Biophys., 1991, 286, 244-251.
83. Colonna, S.; Gaggero, N.; Casella, L.; Carrea, G. and Pasta, P. Tetrahedron: Asymm. 1993, 4, 1325-1330.
84. Allain, E.J.; Hager, L.P.; Deng, L. and Jacobsen, E.N. J. Am. Chem. Soc. 1993, 115, 4415-4416.
85. Zaks, A. and Dodds, D.R. J. Am. Chem. Soc. 1995, 117, 10419-10424.
86. Lakner, F.J. and Hager, L.P. J. Org. Chem. 1996, 61, 3923-3925.
87. Dexter, A.F. and Hager, L.P. J. Am. Chem. Soc. 1995, 117, 817-818.
88. Dexter, A.F.; Lakner, F.J.; Campbell, R.A. and Hager, L.P. J. Am. Chem. Soc. 1995, 117, 6412-6413.
89. Mashino, T.; Nakamura S. and Hirobe, M. Tetrahedron Lett. 1990, 31, 3163-3166.
90. Blée, E. and Schuber, F. Biochem. Biophys. Res. Commun. 1990, 173, 1354-1360.
91. Larrow, J.F. and Jacobsen, E.N. J. Am. Chem. Soc. 1994, 116, 12129-12130.
92. Holland, H.L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992; pp. 55-151.
93. Miller, V.P.; Tschirret-Guth, R.A. and Ortiz de Montellano, P.R. Arch. Biochem. Biophys. 1995, 319, 333-340.
94. Sundaramoothy, M.; Terner, J. and Poulos, T.L. Structure 1995, 3, 1367-1377.
95. Thomas, J.A.; Morris, D.R. and Hager, L.P. J. Biol. Chem. 1970, 245, 3129-3134.
96. Geigert, J.; Dalietos, D.J.; Neidleman, S.L.; Lee, T.D. and Wadsworth, J. Biochem. Biophys. Res. Commun. 1983, 114, 1104-1108.
97. van Deurzen, M.P.J.; van Rantwijk, F. and Sheldon, R.A. J. Carbohydr. Chem. in press.
98. Therapeutic Approaches to Inflammatory Diseases; Lewis, A.J.; Doherty, N.S. and Ackerman, N.R. Eds.; Elsevier: New York, 1989; p. 229.
99. Szabó-Pusztay, K. and Szabó, L. Synth. Commun. 1979, 276-277.
100. Inoue, Y.; Yamamoto, Y.; Suzuki, H. and Takaki, U. in Developments in Selective Oxidations II, Corés Corberán, V. and Vic Bellón, S. Eds.; Elsevier Science: Amsterdam, 1994; pp. 615-622.
101. Goehring, R.R.; Sachdeva, Y.P.; Pisipati, J.S.; Sleevi, M.C. and Wolfe, J.F. J. Am. Chem. Soc. 1985, 107, 435-444.
102. RajanBabu, T.J.; Chenard, B.L. and Petti, M.A. J. Org. Chem. 1986, 51, 1704-1712.
103. Quallich, G.J. and Morrisey, P.M. Synthesis 1993, 51-53.
104. Crestini, C. and Saladino, R. Synth. Commun. 1994, 24, 2835.
105. Corbett, M.D. and Chipko, B.R. Biochem. J. 1979, 183, 269-276.
106. van Deurzen, M.P.J.; van Rantwijk, F. and Sheldon, R.A. J. Mol. Cat. B: Enzymatic 1996, 2, 33-42.
107. Dawson, J.H. Science 1988, 240, 433-439.
108. Du, P. and Loew, G.H. Biophys. J. 1995, 68, 69-80.
109. Kitagawa, T. and Mizutani, Y. Coord. Chem. Rev. 1994, 135/136, 685-735.
110. Poulos, T.L. and Kraut, J. J. Biol. Chem. 1980, 255, 8199-8205.
111. Poulos, T.L. Adv. Inorg. Biochem. 1987, 7, 1-36.
112. Vitello, L.B., Erman, J.E., Miller, M.A., Wang, J. and Kraut, J. Biochemistry 1993, 37, 9807-9818.
113. Miller, M.A.; Shaw, A. and Kraut, J. Struct. Biol. 1994, 1, 524-531.
114. Poulos T.K., J. Biol. Inorg. Chem. 1996, 1, 356-359 and references cited therein.
115. Finzel, B.C.; Poulos, T.L. and Kraut, J. J. Biol. Chem. 1984, 259, 13027-13036.
116. Piontek, K.; Glumoff, T. and Winterhalter, K. FEBS Lett. 1993, 315, 119-124.
117. For a discussion of the role of the axial ligand see: Poulos T.K., J. Biol. Inorg. Chem. 1996, 1, 356-359; Goodin, D.B., J. Biol. Inorg. Chem. 1996, 1, 360-363; Banci, L.; Rosato, A. and Turano, P., J. Biol Inorg. Chem. 1996, 1, 364-367; Gross, Z., J. Biol. Inorg. Chem. 1996, 1, 368-371; Rietjens, I.M.C.M; Osman, A.M.; Veeger, C.; Zakharieva, O.; Antony, J.; Grodzicki, M. and Trautwein, A.X., J. Biol. Inorg. Chem. 1996, 1, 372-376; Weiss, R.; Mandon, D.; Wolter.; T., Trautwein, A.X.; Müther, M.; Bill, E.; Gold, A.; Jayaraj, K. and Terner, J., J. Biol. Inorg. Chem. 1996, 1, 377-383.
118. For a discussion of the role of the axial ligand see: Poulos T.K., J. Biol. Inorg. Chem. 1996, 1, 356-359; Goodin, D.B., J. Biol. Inorg. Chem. 1996, 1, 360-363; Banci, L.; Rosato, A. and Turano, P., J. Biol Inorg. Chem. 1996, 1, 364-367; Gross, Z., J. Biol. Inorg. Chem. 1996, 1, 368-371; Rietjens, I.M.C.M; Osman, A.M.; Veeger, C.; Zakharieva, O.; Antony, J.; Grodzicki, M. and Trautwein, A.X., J. Biol. Inorg. Chem. 1996, 1, 372-376; Weiss, R.; Mandon, D.; Wolter.; T., Trautwein, A.X.; Müther, M.; Bill, E.; Gold, A.; Jayaraj, K. and Terner, J., J. Biol. Inorg. Chem. 1996, 1, 377-383.
119. For a discussion of the role of the axial ligand see: Poulos T.K., J. Biol. Inorg. Chem. 1996, 1, 356-359; Goodin, D.B., J. Biol. Inorg. Chem. 1996, 1, 360-363; Banci, L.; Rosato, A. and Turano, P., J. Biol Inorg. Chem. 1996, 1, 364-367; Gross, Z., J. Biol. Inorg. Chem. 1996, 1, 368-371; Rietjens, I.M.C.M; Osman, A.M.; Veeger, C.; Zakharieva, O.; Antony, J.; Grodzicki, M. and Trautwein, A.X., J. Biol. Inorg. Chem. 1996, 1, 372-376; Weiss, R.; Mandon, D.; Wolter.; T., Trautwein, A.X.; Müther, M.; Bill, E.; Gold, A.; Jayaraj, K. and Terner, J., J. Biol. Inorg. Chem. 1996, 1, 377-383.
120. For a discussion of the role of the axial ligand see: Poulos T.K., J. Biol. Inorg. Chem. 1996, 1, 356-359; Goodin, D.B., J. Biol. Inorg. Chem. 1996, 1, 360-363; Banci, L.; Rosato, A. and Turano, P., J. Biol Inorg. Chem. 1996, 1, 364-367; Gross, Z., J. Biol. Inorg. Chem. 1996, 1, 368-371; Rietjens, I.M.C.M; Osman, A.M.; Veeger, C.; Zakharieva, O.; Antony, J.; Grodzicki, M. and Trautwein, A.X., J. Biol. Inorg. Chem. 1996, 1, 372-376; Weiss, R.; Mandon, D.; Wolter.; T., Trautwein, A.X.; Müther, M.; Bill, E.; Gold, A.; Jayaraj, K. and Terner, J., J. Biol. Inorg. Chem. 1996, 1, 377-383.
121. For a discussion of the role of the axial ligand see: Poulos T.K., J. Biol. Inorg. Chem. 1996, 1, 356-359; Goodin, D.B., J. Biol. Inorg. Chem. 1996, 1, 360-363; Banci, L.; Rosato, A. and Turano, P., J. Biol Inorg. Chem. 1996, 1, 364-367; Gross, Z., J. Biol. Inorg. Chem. 1996, 1, 368-371; Rietjens, I.M.C.M; Osman, A.M.; Veeger, C.; Zakharieva, O.; Antony, J.; Grodzicki, M. and Trautwein, A.X., J. Biol. Inorg. Chem. 1996, 1, 372-376; Weiss, R.; Mandon, D.; Wolter.; T., Trautwein, A.X.; Müther, M.; Bill, E.; Gold, A.; Jayaraj, K. and Terner, J., J. Biol. Inorg. Chem. 1996, 1, 377-383.
122. For a discussion of the role of the axial ligand see: Poulos T.K., J. Biol. Inorg. Chem. 1996, 1, 356-359; Goodin, D.B., J. Biol. Inorg. Chem. 1996, 1, 360-363; Banci, L.; Rosato, A. and Turano, P., J. Biol Inorg. Chem. 1996, 1, 364-367; Gross, Z., J. Biol. Inorg. Chem. 1996, 1, 368-371; Rietjens, I.M.C.M; Osman, A.M.; Veeger, C.; Zakharieva, O.; Antony, J.; Grodzicki, M. and Trautwein, A.X., J. Biol. Inorg. Chem. 1996, 1, 372-376; Weiss, R.; Mandon, D.; Wolter.; T., Trautwein, A.X.; Müther, M.; Bill, E.; Gold, A.; Jayaraj, K. and Terner, J., J. Biol. Inorg. Chem. 1996, 1, 377-383.
123. Edwards, S.L.; Xuong, N.-H.; Hamlin, R.C. and Kraut, J. Biochem. 1987, 26, 1503-1511.
124. Virion, A.; Courtin, F.; Dème, D.; Michot, J.L.; Kaniewski, J. and Pommier, J. Arch. Biochem. Biophys. 1985, 24, 41-47.
125. Ohtaki, S.; Nakagawa, H.; Nakamura, M. and Yamazaki, I. J. Biol. Chem. 1982, 257, 761-766.
126. Harvey, P.J.; Schoemaker, H.E. and Palmer, J.M. FEBS Lett. 1986, 195, 242-246.
127. Schoemaker, H.E.; Lundell, T.K.; Hatakka, A.I. and Piontek, K. FEMS Microbiol. Rev. 1994, 13, 321-332.
128. Wariishi, H.; Valli, K. and Gold, M.H. Biochem. Biophys. Res. Commun. 1991, 176, 269-275.
129. Tuor, U.; Wariishi, H.; Schoemaker, H.E. and Gold, M.H. Biochem. 1992, 31, 4986-4995.
130. Poulos, T.L. and Kraut, J. J. Biol. Chem. 1980, 255, 10322-10330.
131. Ator, M.A. and Ortiz de Montellano, P.R. J. Biol. Chem. 1987, 262, 1542-1551.
132. Ator, M.A.; David, S.K. and Ortiz de Montellano, P.R.J. Biol. Chem. 1987, 262, 14954-14960.
133. Ortiz de Montellano, P.R.; David, S.K.; Ator, M.A. and Tew, D. Biochem. 1988, 27, 5470-5476.
134. DePillis, G.D. and Ortiz de Montellano, P.R. Biochem. 1989, 28, 7947-7952.
135. DePillis, G.D.; Wariishi, H.; Gold, M.H. and Ortiz de Montellano, P.R. Arch. Biochem. Biophys. 1990, 280, 217-223.
136. Harris, R.Z.; Wariishi, H.; Gold, M.H. and Ortiz de Montellano, P.R. J. Biol. Chem. 1991, 266, 8751-8758.
137. Ortiz de Montellano, P.R. and Kerr, D.E. J. Biol. Chem. 1983, 258, 10558-10563.
138. Samokyszyn, V.M. and Ortiz de Montellano, P.R. Biochem. 1991, 30, 11646-11653.
139. Poulos, T.L.; Edwards, S.L.; Wariishi, H. and Gold, M.H. J. Biol. Chem. 1993, 268, 4429-4440.
140. Petersen, J.F.W.; Kadziola, A. and Larsen, S. FEBS Lett. 1994, 339, 291-296.
141. Sundaramoothy, M.; Kishi, K.; Gold, M.H. and Poulos, T.L. J. Biol. Chem. 1994, 269, 32759-32767.
142. Gross, Z. and Nimri, S. J. Am. Chem. Soc. 1995, 117, 8021-8022.
143. Collman, J.P.; Kodadek, T.; Raybuck, S.A.; Brauman, J.I. and Papazian, L.M. J. Am. Chem. Soc. 1985, 107, 4343-4345.
144. Ostovic, D. and Bruice, T.C. J. Am. Chem. Soc. 1989, 111, 6511-6517.
145. Pérez, U. and Dunford, H.B. Biochim. Biophys. Acta 1990, 1038, 98-104.
146. Pérez, U. and Dunford, H.B. Biochem. 1990, 29, 2757-2763.
147. Nakamura, S.; Mashino, T. and Hirobe, M. Tetrahedron Lett. 1992, 33, 5409-5412.
148. Hashimoto, S.; Tatsuno, Y and Kitagawa, T. Proc. Natl. Acad. Sci. USA 1986, 83, 2417-2421.
149. P.R. Ortiz de Montellano in Cytochrome P-450, Structure, Mechanism and Biochemistry, P.R. Ortiz de Montellano, Ed.; Plenum Press: New York, 1986; p. 234.
150. Bagger, S. and Williams, R.J.P. Acta Chem. Scan. 1971, 25, 976-982.
151. Arnao, M.B.; Hernandéz-Ruíz, J.; Varón, R.; García-Cánovas, F. and Acosta, M. J. Mol. Cat. A: Chemical 1995, 104, 179-191.
152. Wilks, A. and Ortiz de Montellano, P.R. J. Biol. Chem. 1993, 268, 22357-22362.
153. Tromp, M.G.M., Olafsson, G., Kren, B.E. and Wever, R. Biochim. Biophys. Acta 1989, 1040 192-198.
154. Divi, R.L. and Doerge, D.R. Biochem. 1994, 33, 9668-9674.
155. Baynton, K.J.; Bewtra, J.K.; Biswas, N. and Taylor, K.E. Biochim. Biophys. Acta 1994, 1206, 272-278.
156. Ma, X. and Rokita, S.E. Biochem. Biophys. Res. Commun. 1988, 157, 160-165.
157. Lambeir, A. and Dunford, H.B. Eur. J. Biochem. 1985, 147, 93-96.
158. Wittenberg, J.B.; Noble, R.W.; Wittenberg, B.A.; Antonini, E.; Brunori, M. and Wyman, J. J. Biol. Chem. 1967, 242, 626-634.
159. Cai, D. and Tien, M. Biochem. Biophys. Res. Commun. 1989, 162, 464-469.
160. Nakajima, R.; Yamazaki, I. and Griffin, B.W. Biochem Biophys. Res. Commun. 1985, 128, 1-6.
161. Yamazaki, H.; Araiso, T.; Hayashi. Y.; Yamada, H. and Makino, R. Adv. Biophys. 1978, 11, 249-281.
162. Butler, A.; Clague, M.J. and Meister, G.E. Chem. Rev. 1994, 94, 625-638.
163. Yamazaki, I. and Piette, L.H. Biochim. Biophys. Acta 1963, 77, 47-64.
164. Tamura, M. and Yamazaki, I. J. Biochem. (Tokio) 1972, 71, 311-319.
165. Chance, B.; Powers, L.; Ching, Y.; Poulos, T.; Schonbaum, G.R.; Yamazaki, I. and Paul, K.G. Arch. Biochem. Biophys. 1984, 235, 596-611.
166. Shaanan, B. J. Mol. Biol. 1983, 171, 31-59; Phillips, S.E.V. and Schoenborn, B.P. Nature 1981, 292, 81-82. See also: Bytheway, I. and Hall, M.B. Chem. Rev. 1994, 94, 639-658; Springer, B.A.; Sligar, S.G.; Olson, J.S. and Phillips, G.N., Jr. Chem. Rev. 1994, 94, 699-714.
167. Shaanan, B. J. Mol. Biol. 1983, 171, 31-59; Phillips, S.E.V. and Schoenborn, B.P. Nature 1981, 292, 81-82. See also: Bytheway, I. and Hall, M.B. Chem. Rev. 1994, 94, 639-658; Springer, B.A.; Sligar, S.G.; Olson, J.S. and Phillips, G.N., Jr. Chem. Rev. 1994, 94, 699-714.
168. Shaanan, B. J. Mol. Biol. 1983, 171, 31-59; Phillips, S.E.V. and Schoenborn, B.P. Nature 1981, 292, 81-82. See also: Bytheway, I. and Hall, M.B. Chem. Rev. 1994, 94, 639-658; Springer, B.A.; Sligar, S.G.; Olson, J.S. and Phillips, G.N., Jr. Chem. Rev. 1994, 94, 699-714.
169. Shaanan, B. J. Mol. Biol. 1983, 171, 31-59; Phillips, S.E.V. and Schoenborn, B.P. Nature 1981, 292, 81-82. See also: Bytheway, I. and Hall, M.B. Chem. Rev. 1994, 94, 639-658; Springer, B.A.; Sligar, S.G.; Olson, J.S. and Phillips, G.N., Jr. Chem. Rev. 1994, 94, 699-714.
170. Pauling, L. and Coryell, C.D. Proc. Natl. Acad. Sci. USA 1936, 22, 210-216.
171. Barr, D.P. and Aust, S.D. Arch. Biochem. Biophys. 1994, 312, 511-515.
172. Chung, N. and Aust, S.D. Arch. Biochem. Biophys. 1995, 316, 8151-8155.
173. van Deurzen, M.P.J.; Seelbach, K.; van Rantwijk, F.; Kragl, U. and Sheldon, R.A. Biocatal. Biotransform. in press.
174. Arnao, M.B.; Acosta, M.; del Río, J.A. and García-Cánovas, F. Biochim. Biophys. Acta 1990, 1038, 85-89.
175. Hiner, A.N.P.; Hernández-Ruíz, J.; García-Cánovas, F.; Smith, A.T.; Arnao, M.B. and Acosta, M. Eur. J. Biochem. 1995, 234, 506-512.
176. Adediran, S.A. Arch. Biochem. Biophys. 1996, 327, 279-284.
177. Kohler, H.; Taurog, A. and Dunford, H.B. Arch. Biochem. Biophys. 1988, 264, 438-449.
178. Vilter, H. Phytochem. 1984, 23, 1387-1390.
179. de Boer, E.; van Kooyk, Y.; Tromp, M.G.M.; Plat, H. and Wever, R. Biochim. Biophys. Acta 1986, 869, 48-53.
180. van Schijndel, J.W.P.M.; Vollenbroek, E.G.M. and Wever, R. Biochim. Biophys. Acta 1993, 1161, 249-256.
181. van Schijndel, J.W.P.M.; Barnett, P.; Roelse, J.; Vollenbroek, E.G.M. and Wever, R. Eur. J. Biochem. 1994, 225, 151-157.
182. Everett, R.R.; Kanofsky, J.R. and Butler, A. J. Biol. Chem. 1990, 265, 4908-4914.
183. de Boer, E.; Plat, H.; Tromp, M.G.M.; Wever, R.; Franssen, M.C.R.; van der Plas, H.C.; Meijer, E.M. and Schoemaker, H.E. Biotechnol. Bioeng. 1987, 30, 607-610.
184. de Boer, E.; Boon, K. and Wever, R. Biochem. 1988, 27, 1629-1635.
185. Butler, A. in Bioinorganic catalysis; Reedijk, J. Ed.; Marcel Dekker: New York, 1993; pp. 425-445.
186. Messerschmidt, A. and Wever, R. Proc. Natl. Acad. Sci. USA 1996, 93, 392-396.
187. Bantleon, R.; Altenbuchner, J. and van Pée, K.-H. J. Bacteriol. 1994, 176, 2339-2347.
188. Weng, M.; Pfeifer, O.; Krauss, S.; Lingens, F. and van Pée, K.-H. J. Gen. Microbiol. 1991, 137, 2539-2546.
189. Itoh, N.; Morinaga, N. and Kouzai, T. Biochim. Biophys. Acta 1994, 1207, 208-216.
190. Hecht, H.J.; Sobek, H.; Haag, T.; Pfeifer, O. and van Pée, K.-H. Struct. Biol. 1994, 1, 532-537.
191. Björkling, F.; Godtfredsen, S.E. and Kirk, O., J. Chem. Soc., Chem. Commun. 1990, 1301-1303; Kirk, O.; Björkling, F. and. Godtfredsen, S.E. (Novo Nordisk A/S), PCT Int. Appl. WO 91 04333; Björkling, F.; Frykman, H.; Godtfredsen, S.E. and Kirk, O., Tetrahedron 1992, 48, 4587-4592; de Zoete, M.C.; van Rantwijk, F.; Maat, L. and Sheldon, R.A., Recl. Trav. Chim. Pays-Bas 1993, 112, 462-463.
192. Björkling, F.; Godtfredsen, S.E. and Kirk, O., J. Chem. Soc., Chem. Commun. 1990, 1301-1303; Kirk, O.; Björkling, F. and. Godtfredsen, S.E. (Novo Nordisk A/S), PCT Int. Appl. WO 91 04333; Björkling, F.; Frykman, H.; Godtfredsen, S.E. and Kirk, O., Tetrahedron 1992, 48, 4587-4592; de Zoete, M.C.; van Rantwijk, F.; Maat, L. and Sheldon, R.A., Recl. Trav. Chim. Pays-Bas 1993, 112, 462-463.
193. Björkling, F.; Godtfredsen, S.E. and Kirk, O., J. Chem. Soc., Chem. Commun. 1990, 1301-1303; Kirk, O.; Björkling, F. and. Godtfredsen, S.E. (Novo Nordisk A/S), PCT Int. Appl. WO 91 04333; Björkling, F.; Frykman, H.; Godtfredsen, S.E. and Kirk, O., Tetrahedron 1992, 48, 4587-4592; de Zoete, M.C.; van Rantwijk, F.; Maat, L. and Sheldon, R.A., Recl. Trav. Chim. Pays-Bas 1993, 112, 462-463.
194. Björkling, F.; Godtfredsen, S.E. and Kirk, O., J. Chem. Soc., Chem. Commun. 1990, 1301-1303; Kirk, O.; Björkling, F. and. Godtfredsen, S.E. (Novo Nordisk A/S), PCT Int. Appl. WO 91 04333; Björkling, F.; Frykman, H.; Godtfredsen, S.E. and Kirk, O., Tetrahedron 1992, 48, 4587-4592; de Zoete, M.C.; van Rantwijk, F.; Maat, L. and Sheldon, R.A., Recl. Trav. Chim. Pays-Bas 1993, 112, 462-463.
195. Flohé, L. in Glutathione, Chemical, Biochemical and Medical Aspects; Dolphin, D.; Avramovic, O. and Poulsen, R. Eds.; Wiley: New York, 1989; pp. 643-731.
196. Ball, A.S. and Trigo, C. Biochem. Soc. Trans. 1995, 23, 272-276.
197. Black, M.; Lin, L. and Guthrie, J. (Medisence, Inc.) PCT Int. Appl. WO 94 27140 [Chem. Abstr. 1995, 122, 182729].
198. Tamaki, H.; Kizaki, T. and Ichikura, S. (Toray Industries) JP 07270414 [Chem. Abstr. 1996, 124, 81501].
199. Yamazaki, M. (Konishiroku Photo Ind.) JP 07306203 [Chem. Abstr. 1996, 124, 255269].
200. Harazono, K.; Kondo, R.and Sakai, K. Appl. Environ. Microbiol. 1996, 62, 913-917.
201. Damhus, T. and Petersen, D.A. (Novo Nordisk A/S.) PCT Int. Appl. WO 95 33039 [Chem. Abstr. 1996, 124, 205673].
202. Lui, D.K.K. and Convents, A.C. (Procter and Gamble Co.) US 5451337 [Chem. Abstr. 1996, 124, 59946].
203. Johnson, M.A. and Pokora, A.P. (Mead Corp.) US 5370770 [Chem. Abstr. 1995, 122, 317211].
204. Allen, R.C. (Exoxemis Inc.) Eur. Pat. Appl. EP 500387 [Chem. Abstr. 1992, 117,184847].
205. Barnett, P.; Hondmann, D.H.; Simons, L.H.; ter Steeg, P.F. and Wever, R. (Unilever N.V.; Unilever PLC) PCT Int. Appl. WO 95 27046 [Chem. Abstr. 1996, 124, 4003].
206. Pellico, M.A. US 5453284 [Chem. Abstr. 1995 123, 265827].
207. Carmichael, R.; Fedorak, P.M. and Pickard, M.A. Biotechnol. Lett. 1985, 7, 289-294.
208. Cooper, V.A.; Nicell, J.A. Water Res. 1996, 30, 954-964.
209. Junino, A.; Andrean, H.; Tuloup, R. and Higgins, I.J. (Oreal S.A.) Eur. Pat. Appl. EP 441689 [Chem. Abstr. 1992 116, 66915].
210. Snelting, H. Chemisch Magazine 1995, 6, 264.
211. Andersen, H.D.; Jensen, E.B. and Welinder, K.G. (Novo Nordisk A/S) Eur. Pat. Appl. EP 505311 [Chem. Abstr. 1993, 118, 74769].
212. Pickard, M.A.; Tenshuk, T.A.; Kadima, A. and Carmichael, R.D. J. Ind. Microbiol. 1991, 7, 235-242.
213. Polvinen, K.; Lehtonen, P.; Leisola, M. and Visuri, K. in Enzymes in Biomass Conversion; Leatham, G.F. and Himmel, M.E. Eds.; Am. Chem. Soc.: Washington, 1991; pp 225-235.
214. Pedersen, A.H.; Vind, J.; Svendsen, A.; Cherry, J.R.; Lamsa, M.; Schneider, P. and Jensen, B.R. (Novo Nordisk A/S) PCT Int. Appl. WO 95 10602 [Chem. Abstr. 1995, 123, 173621].
215. van Deurzen, M.P.J.; Groen, B.W.; van Rantwijk, F. and Sheldon, R.A. Biocatalysis 1994, 10, 247-255.
216. Seelbach, K.; van Deurzen, M.P.J.; van Rantwijk, F.; Sheldon, R.A. and Kragl., U. Biotechnol Bioeng. submitted for publication.