Regioselective biotransformations of dinitriles using Rhodococcus sp. AJ270

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 21, 1997, Pages 3197-3204

  Meth Cohn, Otto ^a   Wang, Mei Xiang ^a  

^a UNIVERSITY OF SUNDERLAND   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748831300     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a703904b     Document Type: Article

References (98)

1. Part of this work has appeared as a preliminary communication; O. Meth-Cohn and M.-X. Wang, Chem. Commun., 1997, 1041.
2. For recent reviews of biotransformations, see (a) H. G. Davies, R. H. Green, D. R. Kelly and S. M. Roberts, Biotransformations in Preparative Organic Chemistry, Academic Press, London, 1989;
3. (b) K. Faber, Biotransformations in Organic Chemistry, Springer Verlag, 1992;
4. (c) Preparative Biotransformations: Whole Cell and Isolated Enzymes in Organic Chemistry, ed. S. M. Roberts, Wiley, New York, 1993;
5. (d) C.-H. Wong and G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Pergamon, 1994;
6. (e) Enzyme Catalysts in Organic Chemistry, ed. K. Drauz and H. Waldmann, VCH, Weinheim, 1995.
7. For recent reviews, see (a) Benign by Design (ACS Symposium Series 577), ed. P. T. Anastas and C. A. Farris, American Chemistry Society, Washington, DC, 1996;
8. (b) T. Lester, Chem. Br., 1996, 45;
9. (c) R. A. Sheldon, Chem. Ind. (London), 1997, 12;
10. (d) Green Chemistry: Designing Chemistry for the Environment (ACS Symposium Series 626), ed. P. T. Anastas and T. C. Williamson, American Chemical Society, Washington, DC, 1996.
11. (a) J. B. Jones, Aldrichimica Acta, 1993, 26, 105;
12. (b) E. Schoffers, A. Golebiowski and C. R. Johnson, Tetrahedron, 1996, 52, 3769.
13. For an overview, see J. Crosby, J. Moilliet, J. S. Parratt and N. J. Turner, J. Chem. Soc., Perkin 1, 1994, 1679.
14. For reviews of nitrile biodegradations, see (a) Cyanide Compounds in Biology (Ciba Foundation Symposium 140), ed. D. Evgred and S. Harnett, Wiley, Chichester, 1988;
15. (b) J.-C. Jallegeas, A. Arnaud and P. Galzy, Adv. Biochem. Eng., 1980, 12, 1;
16. (c) J. L. Legras, G. Chuzel, A. Arnaud and P. Galzy, World J. Microbiol. Biotechnol., 1990, 6, 83.
17. (a) D. B. Harper, Biochem. Soc. Trans., 1976, 4, 502;
18. (b) D. B. Harper, Biochem. J., 1977, 165, 309;
19. (c) M. Kobayashi and S. Shimizu, FEMS Microbiol. Lett., 1994, 120, 217.
20. (a) Y. Asano, Y. Tani and H. Yamada, Agric. Biol. Chem., 1980, 44, 2251;
21. (b) Y. Asano, K. Fujishiro, Y. Tani and H. Yamada, Agric. Biol. Chem., 1982, 46, 1165;
22. (c) Y. Asano, M. Tachibana, Y. Tani and H. Yamada, Agric. Biol. Chem., 1982, 46, 1175.
23. For a useful overview of nitrile-hydrolysing micro-organisms, see O. Meth-Cohn and M.-X. Wang, Tetrahedron Lett., 1995, 36, 9561;
24. O. Meth-Cohn and M.-X. Wang, J. Chem. Soc., Perkin Trans. 1, 1997, 1099 and references cited therein.
25. (a) R. H. Hook and W. G. Robinson, J. Biol. Chem., 1964, 234, 4263;
26. (b) A. K. Bandyopadhyay, T. Nagasawa, Y. Asano, K. Fujishiro, Y. Tani and H. Yamada, Appl. Environ. Microbiol., 1986, 51, 302;
27. (c) M. Kobayashi, T. Nagasawa and H. Yamada, Eur. J. Biochem., 1989, 182, 349;
28. (d) D. E. Stevenson, R. Feng and A. C. Storer, FEBS Lett., 1990, 277, 112;
29. (e) M. Kobayashi, N. Yaanaka, T. Nagasawa and H. Yamada, J. Bacteriol., 1990, 172, 4807;
30. (f) T. Nagasawa, J. Mauger and H. Yamada, Eur. J. Biochem., 1990, 194, 765.
31. (a) Y. Asano, K. Fujishiro, Y. Tani and H. Yamada, Agric. Biol. Chem., 1982, 46, 1165;
32. (b) T. Nagasawa, H. Nanba, K. Ryuno, K. Takeuchi and H. Yamada, Eur. J. Biochem., 1987, 162, 691;
33. (c) T. Nagamune, H. Kurata, M. Hirata, J. Honda, H. Koike, M. Ikeuchi, Y. Inoue, A. Hirata and I. Endo, Biochem. Biophys. Res. Commun., 1990, 168, 437;
34. (d) T. Nagasawa, K. Takeuchi and H. Yamada, Eur. J. Biochem., 1991, 196, 581;
35. (e) M. Kobagashi, M. Nishiyama, T. Nagasawa, S. Horinouchi, T. Beppu and H. Yamada, Biochem. Biophys. Acta, 1991, 1129, 23;
36. (f) W.-Z. Li, Y.-Q. Zhang and H.-F. Yang, Appl. Biochem. Biotechnol., 1992, 36, 171,
37. (g) J. Honda, T. Nagasawa, S. Horionouchi, T. Beppu and H. Yamada, Ann. N. Y. Acad. Sci., 1992, 672, 29;
38. (h) T. Nagasawa, K. Ryuno and H. Yamada, Biochem. Biophys. Res. Commun., 1986, 139, 1305.
39. (a) Y. Asano, M. Tachibana, Y. Tani and H. Yamada, Agric. Biol. Chem., 1982, 46, 1175;
40. (b) M. Kobayashi, H. Komeda, T. Nagasawa, M. Nishiyama, S. Horinouchi, T. Beppu, H. Yamada and S. Shimizu, Eur. J. Biochem., 1993, 217, 327.
41. (a) S. Mahadevan and K. V. Hhimann, Arch. Biochem. Biophys., 1964, 107, 62;
42. (b) M. Kobayashi, N. Yanaka, T. Nagasawa and H. Yamada, Biochemistry, 1992, 31, 9000.
43. (a) T. Nagasawa and H. Yamada, Trends Biotechnol., 1989, 7, 153 and references cited therein;
44. (b) H. Yamada and M. Kobayashi, Biosci. Biotech. Biochem., 1996, 60, 1391 and references cited therein.
45. H. Yamada, Y. Asano and Y. Tani, J. Ferment. Technol., 1980, 58, 495.
46. Y. Asano, S. Ando, Y. Tani and H. Yamada, Agric. Biol. Chem., 1980, 44, 2497.
47. (a) C. Bengis-Garber and A. L. Gutman, Tetrahedron Lett., 1988, 29, 2589;
48. (b) C. Bengis-Garber and A. L. Gutman, Appl. Microbiol. Biotechnol., 1989, 32, 11.
49. M. Kobayashi, N. Yanaka, T. Nagasawa and H. Yamada, Tetrahedron Lett., 1990, 46, 5587.
50. P. Hönicke-Schmidt and M. P. Schneider, J. Chem. Soc. Chem. Commun., 1990, 648.
51. M. A. Cohen, J. Sawden and N. J. Turner, Tetrahedron Lett., 1990, 31, 7223.
52. J. L. Moreau, F. Bigey, S. Azza, A. Arnaud and P. Galzy, Biocatalysis, 1994, 10, 325 and references cited therein.
53. H. Nishise, M. Kurihara and Y. Yani, Agric. Biol. Chem., 1987, 51, 2613.
54. (a) Y. Tani, M. Kurihara, H. Nishise and K. Yamamoto, Agric. Biol. Chem., 1989, 53, 3143;
55. (b) Y. Tani, M. Kurihara and H. Nishise, Agric. Biol. Chem., 1989, 53, 3151;
56. (c) K. Yamamoto, Y. Ueno, K. Otsubo, H. Yamane, K.-I. Komatsu and Y. Tani, J. Ferment. Bioeng., 1992, 73, 125.
57. H. Kaklaye, N. Sakai, A. Sano, M. Yokoyama, T. Sugai and H. Ohta, Chem. Lett., 1991, 1823.
58. (a) J. A. Crosby, J. S. Parratt and N. J. Turner, Tetrahedron: Asymmetry, 1992, 3, 1547;
59. (b) T. Beard, M. A. Cohen, J. S. Parratt, N. J. Turner, J. Crosby and J. Moilliet, Tetrahedron: Asymmetry, 1993, 4, 1085;
60. (c) A. Kerridge, J. S. Parratt, S. M. Roberts, F. Theil, N. J. Turner and A. J. Willetts, Bioorg. Med. Chem. Lett., 1994, 2, 447;
61. (d) S. Maddrell, N. J. Turner, A. Kerridge, A. J. Willetts and J. A. Crosby, Tetrahedron Lett., 1996, 37, 6001.
62. M. Yokoyama, T. Sugai and H. Ohta, Tetrahedron: Asymmetry, 1993, 4, 1081.
63. M. Kobayashi, T. Nagasawa and H. Yamada, Appl. Microbiol. Biotechnol., 1988, 29, 231.
64. L. Martinkova, P. Olsovsky, I. Prepechalova and V. Kren, Biotechnol. Lett., 1995, 17, 1219.
65. C. R. H. I. de Jonge, H. J. Hageman, W. G. B. Huysmans and W. J. Mijs, J. Chem. Soc., Perkin Trans. 1, 1973, 1276.
66. K. Goro, M. Kunihiko and I. Yanosuke, Yuki Gosei Kagaku Kyokai Shi, 1964, 22, 296
67. (Chem. Abstr., 1964, 60, 15 988).
68. (a) P. A. S. Smith and T.-Y. Yu, J. Am. Chem. Soc., 1952, 74, 1096;
69. (b) J. T. Braunholtz and F. C. Mann, J. Chem. Soc., 1953, 1817.
70. N. J. Leonard and M. Oki, J. Am. Chem. Soc., 1955, 77, 6241.
71. P. P. Garcia and J. H. Wood, J. Org. Chem., 1961, 26, 4167.
72. Vogel's Textbook of Practical Organic Chemistry, 5th edn., ed. B. S. Furniss, A. J. Hannaford, P. W. G. Smith and A. R. Tatchell, Longman, London, p. 714.
73. (a) J. E. Francis, D. A. Bennett, J. L. Hyun, S. L. Rovunski, C. L. Amrick, P. S. Loo, D. Murphy, R. F. Neale and D. E. Wilson, J. Med. Chem., 1991, 34, 2899;
74. (b) I. J. G. Climie and D. A. Evans, Tetrahedron, 1982, 38, 697.
75. N. J. Leonard, M. Oki and S. Chiavarelli, J. Am. Chem. Soc., 1955, 77, 6234.
76. O. Kamm and W. H. Newcomb, J. Am. Chem. Soc., 1921, 43, 2228.
77. K. Alexander and L. E. Schniepp, J. Am. Chem. Soc., 1948, 70, 1839.
78. P. A. Delaney, R. A. W. Johnstone and I. D. Entwistle, J. Chem. Soc., Perkin Trans. 1, 1986, 1855.
79. N. Furukawa, S. Ogawa, T. Kawai and S. Oae, J. Chem. Soc., Perkin Trans. 1, 1984, 1839.
80. D. J. G. Ives and K. Sames, J. Chem. Soc., 1943, 513.
81. A. Ishigaki, M. Oue, Y. Matsushita, I. Masuda and T. Shono, Bull. Chem. Soc. Jpn., 1977, 50, 726.
82. D. V. Rao, F. A. Stuber and H. Ulrich, J. Org. Chem., 1979, 44, 456.
83. J. D. Hobson and J. R. Malpass, J. Chem. Soc C., 1967, 1645.
84. H. J. Reich, J. M. Renga and I. Reich, J. Am. Chem. Soc., 1975, 97, 5434.
85. C. R. Smith Jr., M. O. Ragby, R. L. Lohmar, C. A. Glass and I. A. Wolff, J. Org. Chem., 1960, 25, 218.
86. M. D. Soffer, N. S. Strauss, M. D. Trail and K. W. Sherk, J. Am. Chem. Soc., 1947, 69, 1685.
87. K. Saotome and K. Sato, Bull. Chem. Soc. Jpn., 1966, 39, 485.
88. T. L. Gresham, J. E. Jansen, F. W. Shaver and J. T. Gregory, J. Am. Chem. Soc., 1948, 70, 990.
89. C. G. Overberger, P. Barkan, A. Lusi and H. Ringsdorf, J. Am. Chem. Soc., 1962, 84, 2814.
90. J. O. Halford and B. Weissmann, J. Org. Chem., 1953, 18, 30.
91. J. Gardent and G. Hazebroucq, Bull. Soc. Chim. Fr., 1968, 600.
92. C. W. Moore and J. F. Thorpe, J. Chem. Soc., 1908, 93, 165.
93. M. N. Bogdanov, G. I. Kudryavtsev and I. A. Spirina, J. Gen. Chem. USSR (Eng. Transl), 1960, 30, 282.
94. T. R. Demmin and M. M. Rogic, J. Org. Chem., 1980, 45, 2737.
95. L. A. Carpino, J. Am. Chem. Soc., 1962, 84, 2196.
96. A. R. Forrester, A. S. Ingram and R. H. Thomson, J. Chem. Soc., Perkin Trans. 1, 1972, 2847.
97. M. Kilpatrick and R. D. Eanes, J. Am. Chem. Soc., 1943, 65, 589.
98. M. Levine and R. Sedlecky, J. Org. Chem., 1959, 24, 115.