The steric course of enzymic hydroxylation at primary carbon atoms

Tetrahedron

Volumn 54, Issue 20, 1998, Pages 5005-5040

  Shapiro, S ^a   Caspi, E ^b  

^a Mund und Kieferheilkunde der U   (Switzerland)

^b UNIVERSITY OF MASSACHUSETTS MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBON; STEROID; STEROL;

AEROBIC METABOLISM; ANAEROBIC METABOLISM; BIOSYNTHESIS; CATALYSIS; CYCLIZATION; HYDROXYLATION; OXIDATIVE STRESS; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY; STEROIDOGENESIS; STEROL SYNTHESIS;

EID: 0032516253     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)01040-5     Document Type: Review

References (194)

1. 1. Urey, H. C. Proc. Nat. Acad. Sci. USA 1952, 38, 351-363.
2. 2. Kastner, J. F. Orig. Life Evol. Biosph. 1990, 20, 199-231.
3. 3. Tajika, E.; Matsui, T. Earth Planet. Sci. Lett. 1992, 113, 251-266.
4. 4. Kastings, J. F. Science 1993, 259, 920-926.
5. 5. Schropf, J. W. Science 1993, 260, 640-646.
6. 6. Vinogradov, A. P. The Origin of the Biosphere. In: Clark, F.; Synge R. L. M., Ed. The Origin of Life on the Earth (Proc. 1st Int. Symp., Moscow, 19-24 Aug 1957). London, Pergamon Press, 1959, 23-37.
7. 7. Kropotkin, P. N. The geological conditions for the appearance of life on the earth, and the problems of petroleum genesis. Ibid., 1959, 84-94
8. 8. Huber, C.; Wächterhäuser, G. Science 1997, 276, 245-247.
9. 9. Ourisson, G.; Rohmer, M.; Anton, R. From Terpenes to Sterols, Macroevolution and Microevolution. In: Swain T.; Waller G. R., Eds. Recent Advances in Phytochemistry (Topics in the Biochemistry of Natural Products, vol 13). New York, Plenum Press, 1978, 131-162.
10. 10. Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. Helv. Chim. Acta 1955, 38, 1890-1904.
11. 11. Ageta, H.; Shiojima, K.; Suzuki, H.; Nakamura, S. Chem. Pharm. Bull. 1993, 41, 1939-1943.
12. 12. Corey, E. J.; Russey, W. E.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1966, 88, 4750-4751.
13. 13. van Tamelen, E. E.; Willett, J. D.; Clayton, R. B.; Lord, K. E. J. Am. Chem. Soc. 1966, 88, 4752-4754.
14. 14. Nes, W. R.; McKean, M. L. Biochemistry of Steroids and Other Isopentenoids. Baltimore, University Park Press, 1977, 229-270.
15. 15. Caspi, E. Tetrahedron 1986, 42, 3-50.
16. 16. Berti, G.; Bottari, F.; Marsili, A.; Morelli, I.; Mandelbaum, A. Chem. Commun. 1967, 50-51.
17. 17. Zander, J. M.; Caspi, E.; Pandey, G. N.; Mitra, C. R. Phytochemistry 1969, 8, 2265-2267.
18. 18. Barton, D. H. R.; Mellows, G.; Widdowson, D. A. J. Chem. Soc. (C) 1971, 110-116.
19. 19. Nakanishi, T.; Inatomi, Y.; Nishi, M.; Murata, H.; Inada, A.; Aibara, S. Chem. Pharm. Bull. 1995, 43, 2256-2260.
20. 20. Marsili, A.; Morelli, I. Phytochemistry 1968, 7, 1705-1706.
21. 21. Huneck, S. Fortschr. Chem. Org. Naturst. 1971, 29, 209-306.
22. 22. Ejiri, H.; Shibata, S. Phytochemistry 1974, 13, 2871.
23. 23. Conner, R. L.; Mallory, F. B. Biosynthesis of sterols and pentacyclic triterpenoids in Tetrahymena pyriformis. In: Schubert, K., Ed. Abh Deut Akad Wiss Berlin, K1 Med no. 2 (Symp. biochem. Aspekte Steroidforschung, 18-21 Sep 1967). East Berlin, Akademie Verlag, 1969, 5-16.
24. 24. Caspi, E. Acc. Chem. Res. 1980, 13, 97-104.
25. 25. Rohmer, M.; Bouvier, P.; Ourisson, G. Eur. J. Biochem. 1980, 112, 557-560.
26. 26. Sahm, H.; Rohmer, M.; Bringer-Meyer, S.; Sprenger, G. A.; Welle, R. Adv. Microb. Physiol. 1993, 35, 249-273.
27. 27. Rohmer, M. Pure. Appl. Chem. 1993, 65, 1293-1298.
28. 28. Herrmann, D.; Bisseret, P.; Connan, J.; Rohmer, M. FEMS Microbiol Lett. 1996, 135, 323-326.
29. 29. Caspi, E.; Greig, J. B.; Zander, J. M. Biochem. J. 1968, 109, 931-932.
30. 30. Aberhart, D. J.; Caspi, E. J. Am. Chem. Soc. 1979, 101, 1013-1019.
31. 31. Zander, J. M.; Greig, J. B.; Caspi, E. J. Biol. Chem. 1970, 245, 1247-1254.
32. 32. Tanaka, R.; Matsunaga, S. Phytochemistry 1992, 31, 3535-3539.
33. 33. Day, W. Genesis of Planet Earth. East Lansing, MI, House of Talos Publishing Co., 1979, 71-79.
34. 34. Day, W. Ibid., 89-115.
35. 35. Ho, R. Y. N.; Liebman, J. F.; Valentine, J. S. Biological Reactions of Dioxygen, an Introduction. In: Valentine, J. S.; Foote, C. S.; Greenberg, A.; Liebman, J. F., Eds. Active Oxygen in Biochemistry. Glasgow, Blackie Academic & Professional, 1995, 1-36.
36. 36. Kodera, M.; Kano, K.; Funabiki, T. Nonheme monooxygenases. In: Funabiki, T., Ed. Oxygenases and Model Systems. Dordrecht, NL, Kluwer Academic Publishers, 1997, 1-18.
37. 37. Weber, G.; Waxman, D. J. Arch. Biochem. Biophys. 1993, 307, 369-378.
38. 38. Ziegler, D. M. Annu. Rev. Pharmacol. Toxicol. 1993, 33, 179-199.
39. 39. Jones, K. H.; Smith, R. T.; Trudgill, P. W. J. Gen. Microbiol. 1993, 139, 797-805.
40. 40. Wright, M. A.; Taylor, I. N.; Lenn, M. J.; Kelly, D. R, Mahdi, J. G.; Knowles C. J. FEMS Microbiol. Lett. 1994, 67-72.
41. 41. Gagnon, R.; Grogan, G.; Levitt, M. S.; Roberts, S. M.; Wan, P. W. H.; Willetts A. J. J. Chem. Soc., Perkin Trans. 1 1994, 2537-2543.
42. 42. Schuler, M. A. Crit. Rev. Plant. Sci. 1996, 15, 235-284.
43. 43. Colonna, S.; Gaggero, N.; Pasta, P.; Ottolina, G. Chem. Commun. 1996, 2303-2307.
44. 44. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
45. 45. Lewis, D. F. V. Cytochromes P450. Structure, Function and Mechanism. London, Taylor & Francis, Ltd, 1996, 50-54.
46. 46. Jones, D. F.; Howe, R. J. Chem. Soc. (C) 1968, 2801-2808.
47. 47. Jones, D. F. J. Chem. Soc. (C) 1968, 2827-2833.
48. 49-51
49. 49. Yarrow, D.; Meyer, S. A. Int. J. Syst. Bacteriol. 1978, 28, 611-615.
50. 50. Meyer, S. A.; Ahearn, D. G.; Yarrow, D. Candida Berkhout. In: Kreger-van Rij, N. J. W., Ed. The Yeasts, A Taxonomic Study, 3rd edn. Amsterdam, Elsevier Publishers B.V., 1984, 585-844.
51. 51. Barnett, J. A.; Payne, R. W.; Yarrow, D. Yeast, Characteristics and Identification, 2nd edition. UK, Cambridge University Press, 1990, 170.
52. 52. Popják, G.; Cornforth, J. W. Biochem. J. 1966, 101, 553-568.
53. 53. Greenwood, D. R.; Rees, H. H. Biochem. J. 1982, 208, 857-864.
54. 54. Hayano, M.; Gut, M.; Dorfman, R. I.; Sebek, O. K.; Peterson, D. H. J. Am. Chem. Soc. 1958, 80, 2336-2337.
55. 55. Corey, E. J.; Gregoriou, G. A.; Peterson, D. H. J. Am. Chem. Soc. 1958, 80, 2338.
56. 56. Hayano, M.; Gut, M.; Dorfman, R. I.; Schubert, A.; Siebert, R. Biochim. Biophys. Acta. 1959, 32, 269-270.
57. 57. Ramm, P. J.; Caspi, E. J. Biol. Chem. 1969, 244, 6064-6073.
58. 58. Ebersole, R. C.; Godtfredsen, W. O.; Vangedal, S.; Caspi, E. J. Am. Chem. Soc. 1973, 95, 8133-8134.
59. 59. Ebersole, R. C.; Godtfredsen, W. O.; Vangedal, S.; Caspi, E. J. Am. Chem. Soc. 1974, 96, 6499-6501.
60. 60. Caspi, E.; Ebersole, R. C.; Mulheirn, L. J.; Godtfredsen, W. O.; von Daehne, W. J. Ster. Biochem. 1973, 4, 433-437.
61. 61. Varma, K. R.; Caspi, E. Phytochemistry 1970, 9, 1539-1543.
62. 62. Bergstrom, S.; Lindstredt, S.; Samuelson, B.; Corey, E. J.; Gregoriou, G. A. J. Am. Chem. Soc. 1958, 80, 2337-2338.
63. 63. Spike, T. E.; Wang, A. H.-J.; Paul, I. C.; Schroepfer, Jr. GJ. J. Chem. Soc.; Chem. Commun. 1974, 477-478.
64. 64. Burstein, S.; Middleditch, B. S.; Gut, M. J. Biol. Chem. 1975, 250, 9028-9037.
65. 66-68
66. 66. von Arx, J. A. Phytopathol. Z. 1957, 29, 413-468.
67. 67. von Arx, J. A. Plant Pathogenic Fungi (Beih. Nova Hedwigia no. 87), Berlin-Stuttgart, J. Cramer, 1987, 80-81, 218-220.
68. 68. Farr, D. F.; Bills, G. F.; Chamuris, G. P.; Rossman, A. Y. Fungi on Plants and Plant Products in the United States. St Paul, MN, American Phytopathological Society, 1987, 638.
69. 69. Njar, V. C. O.; Shapiro, S.; Arunachalam, T.; Caspi, E. J. Steroid. Biochem. 1985, 22, 339-400.
70. 70. Tschesche, R.; Lilienweiss, G. Z. Naturforsch. 1964, 19B, 265-266.
71. 71. Tschesche, R.; Brassat, B. Z. Naturforsch. 1966, 21B, 894-895.
72. 72. Caspi, E.; Lewis, D. O. Science 1967, 156, 519-520.
73. 73. Sauer, H. H.; Bennett, R. D.; Heftmann, E. Phytochemistry 1967, 6, 1521-1526.
74. 74. Bennett, R. D.; Sauer, H. H.; Heftmann, E. Phytochemistry 1968, 7, 41-50.
75. 75. Caspi, E.; Wickramasinghe, J. A. F.; Lewis, D. O. Biochem. J. 1968, 108, 499-503.
76. 76. Caspi, E.; Lewis, D. O.; Piatak, D. M.; Thimann, K. V.; Winter, A. Experientia 1966, 22, 506-507.
77. 77. Wickramasinghe, J. A. F.; Hirsch, P. C.; Munavalli, SM, Caspi, E. Biochemistry 1968, 7, 3248-3253.
78. 78. Caspi, E. Biosynthesis of Plant Sterols. 5. Formation of Cardenolides in Digitalis Plants. In: Schubert, K., Ed. Abh. Deut. Akad. Wiss. Berlin, K1 Med no. 2 (Symp. biochem. Aspekte Steroidforschung, 18-21 Sep 1967). East Berlin, Akademie Verlag, 1969, 17-29.
79. 79. Bennett, R. D.; Heftmann, E.; Winter, B. J. Phytochemistry 1969, 8, 2325-28.
80. 80. Tschesche, R.; Brassat, B. Z. Naturforsch. 1965, 20B, 707-708.
81. 81. Caspi, E.; Lewis, D. O. Phytochemistry 1968, 7, 683-691.
82. 82. March, J. Advanced Organic Chemistry, Reactions, Mechanisms, and Structure. New York, John Wiley & Sons Inc, 1992, 294-296.
83. 83. The same order holds for the facility of hydrogen abstraction from saturated hydrocarbons, see ref. 36.
84. 84. Paul, A.; Yang, M. X.; Bent, B. E. Surf. Sci. 1993, 297, 327-344.
85. 85. Gallo, R.; Lazzeri, V. Appl. Catal. 1996, 146A, 87-106.
86. 86. A disproportionate reaction of the type ROOH+R′H*→R′OH+ROH* was also considered, wherein a peroxide (ROOH) approaches the cardenolide C-14 position (R′H*) from the β-face and donates an hydroxy group to this atom (R′OH), accompanied by liberation of the 14α-H atom (H*) as ROH*. The problem remains, however, as to how such a reaction, by whatever mechanism, can surmount the extremely high energy barrier to inversion of the rigid, hindered C-14 chiral centre. Reactions with the indicated stoichiometry are in fact known, but these reportedly proceed with retention of configuration. See Sawaki, Y. Epoxidation and Hydroxylation. In: Patai, S., Ed. The Chemistry of Hydroxyl, Ether and Peroxide Groups. Chichester, UK, John Wiley & Sons, 1993, 587-656.
87. 87. Aulabaugh, A. E.; Crouch, R. C.; Martin, G. E.; Ragouzeos, A.; Shockcor, J. P.; Spitzer, T. D.; Farrant, R. D.; Hudson, B. D.; Lindon, J. C. Carbohyd. Res. 1992, 230, 201-212.
88. 88. Theurer, C.; Treumann, H.-J.; Faust, T.; May, U.; Kreis, W. Plant Cell. Tissue Organ. Cult. 1994, 38, 327-335.
89. 89. Canonica, L.; Ronchetti, F.; Russo, G. Chem. Commun. 1970, 1675-1677.
90. 90. Njar, VCO.; Arunachalam, T.; Caspi, E. J. Org. Chem. 1983, 48, 1412-1414.
91. 91. Ogston, A. G. Nature 1948, 162, 963.
92. 92. Sokolov, V. I.; Zefirov, N. S. Dokl. Chem. [Engl. trans.] 1991, 319, 219-220.
93. 93. Azerad, R. Bull. Soc. Chim. Fr. 1995, 132, 17-51.
94. 14C]acetate via the intermediacy of citrate. Since this theoretical explanation was propounded, evidence has accrued for an actual physical three-point attachment of substrate to target leading to discrimination between the two 'identical' moieties in a prochiral substrate, e.g.; see refs. 95-98.
95. 95. Glusker, J. P. Curr. Top. Cell. Regulat. 1992, 33, 169-184.
96. 96. Kano, K.; Yoshiyasu, K.; Yasuoka, H.; Hata, S.; Hashimoto, S. J. Chem. Soc., Perkin Trans. 2 1992, 1265-1269.
97. 97. Lauble, H.; Kennedy, M. C.; Beinert, H.; Stout, C. D. Biochemistry 1992, 31, 2735-2748.
98. 98. Davankov V. A. J. Chromatogr. 1994, 666A, 55-76.
99. 99. Cornforth, J. W.; Redmond, J. W.; Eggerer, H.; Buckel, W.; Gutschow, C. Nature 1969, 221, 1212-1213.
100. 100. Cornforth, J. W.; Redmond, J. W.; Eggerer, H.; Buckel, W.; Gutschow, C. Eur. J. Biochem. 1970, 14, 1-13.
101. 101. Lüthy, J.; Rétey, J.; Arigoni, D. Nature 1969, 221, 1213-12115.
102. 102. Floss, H. G.; Tsai, M. D. Adv. Enzymol. Relat. Areas Molec. Biol. 1979, 50, 243-302.
103. 103. Caspi, E.; Piper, J.; Shapiro, S. J. Chem. Soc., Chem. Commun. 1981, 77-79.
104. 104. Caspi, E.; Shapiro, S.; Piper, J. U. Tetrahedron 1981, 37, 3535-3543.
105. 105. Caspi, E.; Eck, C. R. J. Org. Chem. 1977, 42, 767-768.
106. 106. Cummings, J. G.; Thorpe, C. Biochemistry 1994, 33, 788-797.
107. 107. Shapiro, S.; Piper, J. U.; Caspi, E. Anal. Biochem. 1981, 117, 113-120.
108. 108. Hinson, J. A.; Neal, R. A. Biochim. Biophys. Acta 1975, 384, 1-11.
109. 109. Günther, H.; Biller, F.; Simon, H. Angew. Chem. Int. Ed. Engl. 1973, 12, 146-147.
110. 110. Günther, H.; Alizade, M. A.; Kellner, M.; Biller, F.; Simon, H. Z. Naturforsch. 1973, 28C, 241-246.
111. 111. Coon, M. J.; White, R. E.; Nordblum, G. D.; Ballou, D. P.; Guengerich, F. P. Croat. Chem. Acta 1977, 49, 163-177.
112. 112. Akhrem, A. A, Metelitza, D. I.; Bielski, S. M.; Kiselev, P. A.; Skurko, M. E.; Usanov, S. A. Croat. Chem. Acta. 1977, 49, 223-235.
113. 113. Walsh, C. T. Annu. Rep. Med. Chem. 1980, 15, 207-216.
114. 114. Stetten, D. J. Biol. Chem. 1943, 147, 327-332.
115. 115. Kolattukudy, P. E.; Hankin, L. J. Nutr. 1966, 90, 167-174.
116. 116. Street, J. C. Ann. N.Y. Acad. Sci. 1969, 160, 274-290.
117. 117. Coon, M. J.; Strobel, H. W.; Heidema, J. K.; Kaschnitz, R. M.; Autor, A. P.; Ballou, D. P. On the Mechanism of Hydroxylation Reactions in Reconstituted Liver Microsomal Enzyme System Containing Cytochrome P-450. In: Schultz, J., Cameron, B. T., Eds. The Molecular Basis of Electron Transport (Proc Miami Winter Symp, 13-14 Jan 1972, vol 4). New York, Academic Press, 1972, 231-250.
118. 118. Bernhard, K.; Gloor, U.; Scheitlin, E. Helv. Chim. Acta. 1952, 35, 1908-1913.
119. 119. Das, M. L.; Orrenius, S.; Ernster, L. Eur. J. Biochem. 1968, 4, 519-523.
120. 120. Ichihara, K.; Kusunose, E.; Kusunose, M. Biochim. Biophys. Acta 1969, 176, 713-719.
121. 121. Frommer, U.; Ullrich, V.; Staudinger, H. Hoppe-Seylers Z. Physiol. Chem. 1970, 351, 903-912.
122. 122. Frommer, U.; Ullrich, V.; Staudinger, H.; Orrenius, S. Biochim. Biophys. Acta 1972, 280, 487-494.
123. 123. Frommer, U.; Ullrich, V.; Orrenius, S. FEBS Lett. 1974, 41, 14-16.
124. 124. Kiel, J. L. Type-b Cytochromes, Sensors and Switches. Boca Raton, FL, CRC Press, 1995, 7.
125. 125. Ruettinger, R. T.; Griffith, G. R.; Coon, M. J. Arch. Biochem. Biophys. 1977, 183, 528-537.
126. 126. Shapiro, S.; Piper, J. U.; Caspi, E. J. Am. Chem. Soc. 1982, 104, 2301-2305.
127. 127. Gautier, A. Sterischer Verlauf einiger chemischer und biochemischer Reaktionen an Substraten mit chiral Methylgruppe, Eidg Techn Hochsch Zürich (Diss Naturwiss no. 6583) 1980.
128. 128. Priestley, N. D.; Floss, H. G.; Froland, W. A.; Lipscomb, J. D.; Williams, P. G.; Morimoto, H. J. Am. Chem. Soc. 1992, 114, 7561-7562.
129. 129. Wilkinson, B.; Zhu, M.; Priestley, N. D.; Nguyen, H.-H.T.; Morimoto, H.; Williams, P. G, Chan, S. I.; Floss, H. G. J. Am. Chem. Soc. 1996, 118, 921-922.
130. 130. Meyer, A. S. Experientia 1955, 11, 99-102.
131. 131. Meyer, A. S. Biochim. Biophys. Acta 1955, 17, 441-442.
132. 132. Thompson, Jr. E. A.; Siiteri, P. K. J. Biol. Chem. 1974, 249, 5373-5378.
133. 133. Arigoni, D.; Battaglia, R.; Akhtar, M.; Smith, T. J. Chem. Soc., Chem. Commun. 1975, 185-186.
134. 134. Osawa, Y.; Shibata, K.; Rohrer, D.; Weeks, C.; Duax, W. L. J. Am. Chem. Soc. 1975, 97, 4400-4402.
135. 135. Caspi, E.; Santaniello, E.; Patel, K.; Arunachalam, T.; Eck, C. R. J. Am. Chem. Soc. 1978, 100, 5223-5224.
136. 136. Akhtar, M.; Calder, M. R.; Corina, D. L.; Wright, J. N. Biochem. J. 1982, 201, 569-580.
137. 137. Stevenson, D. E.; Wright, J. N.; Akhtar, M. J. Chem. Soc., Perkin Trans. 1 1988, 2043-2052.
138. 138. Wright, J. N.; Akhtar, M. Steroids 1990, 55, 142-151.
139. 143
140. 140. Goto, J.; Fishman, J. Science 1977, 195, 80-81.
141. 141. Hosoda, H.; Fishman, J. J. Am. Chem. Soc. 1974, 96, 7325-7329.
142. 142. Caspi, E.; Dhamaratne, H. R. W, Roitman, E.; Shackleton, C. J. Chem. Soc., Perkin Trans. 1 1993, 1191-1195.
143. 143. Cole, P. A.; Robinson, C. H. Biochem. J. 1990, 268, 553-561.
144. 144. Caspi, E.; Arunachalam, T.; Nelson, P. A. J. Am. Chem. Soc. 1983, 105, 6987-6989.
145. 145. Caspi, E.; Arunachalam, T.; Nelson, P. A. J. Am. Chem. Soc. 1986, 108, 1847-1852.
146. 146. Miyaki, S.; Fishman, J. Differential Isotope Effects in the C-19 Hydroxylative Steps of Aromatization. 7th Int Congr Endocrinol, Québec, 1-7 Jul 1984, Abst. no. 1620.
147. 147. Caspi, E.; Santaniello, E.; Patel, K.; Arunachalam, T. J. Chem. Soc.; Chem. Commun. 1984, 379-381.
148. 148. Arunachalam, T.; Santaniello, E.; Patel, K.; Caspi, E. J. Chem. Soc., Perkin Trans. 1 1987, 61-69.
149. 149. Haubenstock, H. J. J. Org. Chem. 1973, 38, 1765-1767.
150. 150. Landauer, S. R.; Rydon, H. N. J. Chem. Soc. 1953, 2224-2234.
151. 151. Arunachalam, T.; Longcope, C.; Caspi, E. J. Biol. Chem. 1979, 254, 5900-5905.
152. 152. Caspi, E.; Chang, C. C.; Busch, K. H.; Arunachalam, T. Croat. Chem. Acta 1985, 58, 443-451.
153. 153. Jones, J. P.; Rettie, A. E.; Trager, W. F. J. Med. Chem. 1990, 33, 1242-1246.
154. 154. Fretz, H.; Waggon, W.-D. Helv. Chim. Acta 1989, 72, 391-400.
155. 156-158 the methylene groups of normal paraffins are reportedly inert to hydroxylation by this bacterium.)
156. 156. Baptist, J. N.; Gholson, R. K.; Coon, M. J. Biochim. Biophys. Acta 1963, 69, 40-47.
157. 157. May, S. W.; Schwartz, R. D.; Abbott, B. J.; Zaborsky, O. R. Biochim. Biophys. Acta 1975, 403, 245-255.
158. 158. May, S. W. Enzymic Epoxidation and Oxygen Activation. In: Rylander, P. N.; Greenfield, H.; Eds. Catalysis in Organic Synthesis. New York, Academic Press Inc., 1976, 101-111.
159. 159. Korzekwa, K. R.; Jones, J. P.; Gillette, J. R. J. Am. Chem. Soc. 1990, 112, 7042-7046.
160. 160. CaJacob, C. A.; Chan, W. K.; Shephard, E.; Ortiz de Montellano, P. R. J. Biol. Chem. 1988, 263, 18640-18649.
161. 161. Hamilton, G. A. J. Am. Chem. Soc. 1964, 86, 3391-3392.
162. 162. Bach, R. D.; MacDouall, J. J. W.; Owensby, A. L.; Schlegel, H. B. J. Am. Chem. Soc. 1990, 112, 7065-7067.
163. 163. Skell, P. S.; Woodworth, R. C. J. Am. Chem. Soc. 1956, 78, 4496-4497.
164. 164. von E. Doering, W.; Prinzbach, H. Tetrahedron 1959, 6, 24-30.
165. 165. Hill, E. A. J. Org. Chem. 1972, 37, 4008-4012.
166. +). WATOC '96 (Progr. 4th World Congress Theoretically Oriented Chemistry, Jerusalem, Israel, 7-12 Jul 1996), Electr. poster no. 17, p. 48; http://www.ch.ic.ac.uk/watoc/abstracts/17/-
167. 167. Groves, J. T.; Van Der Puy, M. J. Am. Chem. Soc. 1974, 96, 5274-5275.
168. 168. Groves, J. T.; McClusky, G. A. J. Am. Chem. Soc. 1976, 98, 859-861.
169. 169. Groves, J. T.; Van Der Puy, M. J. Am. Chem. Soc. 1976, 98, 5290-5297.
170. 170. Groves, J. T.; McClusky, G. A.; White, R. E.; Coon, M. J. Biochem. Biophys. Res. Commun. 1978, 81, 154-160.
171. 171. White, R. E.; Groves, J. T.; McClusky, G. A. Acta Biol. Med. Ger. 1979, 38, 475-482.
172. 172. Ingles, D. L. Aust. J. Chem. 1973, 26, 1021-1029.
173. 173. Cohen, G.; Cederbaum, A. I. Science 1979, 204, 66-68.
174. 174. White, R. E.; McCarthy, M. B. Arch. Biochem. Biophys. 1986, 246, 19-32.
175. 175. Khenkin, A. M.; Sorokin, A. B.; Shilov, A. E. Mechanism of Alkane Oxidation Catalysed by Cytochrome P-450 and its Models. In: Archakov, A. I., Bachmanova, G. I., Eds. Cytochrome P-450. Biochemistry and Biophysics (Proc. 7th Int. Conf. Biochem. Biophys. Cyt. P-450, Struct Func Biotechnol Ecol Aspects, Moscow, 28 Jul-2 Aug 1991). Moscow, INCO-TNC, Joint Stock Co., 1992, 39-44.
176. 176. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5699-5707.
177. 177. Shea, J. P.; Nelson, S. D.; Ford, G. P. J. Am. Chem. Soc. 1983, 105, 5451-5454.
178. T) for hydroxylation of the methyl termini of n-octane by Ps. oleovorans monooxygenase awaits experimental evaluation.
179. 179. Jones, J. P.; Trager, W. F. J. Am. Chem. Soc. 1987, 109, 2171-2173.
180. 180. Fretz, H.; Waggon, W.-D. Helv. Chim. Acta 1986, 69, 1959-1970.
181. 181. Northrop, D. B. Biochemistry 1975, 14, 2644-2651.
182. 182. Miyairi, S.; Fishman, J. J. Biol. Chem. 1985, 260, 320-325.
183. 183. Timmers, R. J. M.; Lambert, J. G. D. Comp. Biochem. Physiol. 1987, 88B, 453-456.
184. 184. Norton, B. I.; Miyairi, S.; Fishman, J. Endocrinology 1988, 122, 1047-1052.
185. 185. Numazawa, M.; Midzuhashi, K.; Nagaoka, M. Biochem. Pharmacol. 1994, 47, 717-726.
186. 186. Lorand, J. P.; Grant, R. W.; Samuel, P. A.; O'Connell, E. M, Zaro, J.; Pilotte, J.; Wallace, R. W. J. Org. Chem. 1973, 38, 1813-1821.
187. 187. Lorand, J. P. J. Am. Chem. Soc. 1974, 96, 2867-2874.
188. 188. Newcomb, M.; Le Tadic-Biadatti, M.-H.; Chestney, D. L.; Roberts, E. S.; Hollenberg, P. F. J. Am. Chem. Soc. 1995, 117, 12085-12091.
189. 189. Pacansky, J.; Dupuis, M. J. J. Am. Chem. Soc. 1982, 104, 415-421. Torsional barriers to internal rotation of n-alkyl C-C-radicals seem to be much lower than torsional barriers to internal rotation of alkyl methyl groups (cf. ref. 190).
190. 190. Cohen, N.; Benson, S. W. The Thermochemistry of Alkanes and Cycloalkanes. In: Patai, S., Rappoport, Z., Eds. The Chemistry of Alkanes and Cycloalkanes. Chichester, UK, John Wiley & Sons, 1992, 215-287.
191. 191. Chen, K. S.; Edge, D. J, Kochi, J. K. J. Am. Chem. Soc. 1973, 95, 7036-7043.
192. 192. Testa, B. The Metabolism of Drugs and Other Xenobiotics. Biochemistry of Redox Reactions. London, Academic Press Ltd, 1995, 125.
193. 193. Siegbahn, P. E. M.; Crabtree, R. H. J. Am. Chem. Soc. 1997, 119, 3103-3113.
194. 194. Valentine, A. M.; Wilkinson, B.; Liu, K. E.; Komar-Panicucci, S.; Priestley, N. D.; Williams, P. G.; Morimoto, H.; Floss, H. G.; Lippard, S. J. J. Am. Chem. Soc. 1997, 119, 1818-1827.