Biocatalysis in Organic Synthesis: The Use of Nitrile- and Amide-hydrolyzing Microorganisms

Bioscience, Biotechnology and Biochemistry

Volumn 61, Issue 9, 1997, Pages 1419-1427

  Sugai, Takeshi ^a   Yamazaki, Takahiro ^a   Yokoyama, Masahiro ^a   Ohta, Hiromichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Amide; Hydrolysis; Microorganisms; Nitrile; Organic synthesis

Indexed keywords

EID: 0001093905     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.61.1419     Document Type: Article

References (103)

1. J. D. Downer, in “Rodd’s Chemistry of Carbon Compounds,” Vol. II, Part A, Elsevier, Amsterdam, 1971, p. 192;
2. “Oxidation in Organic Chemistry,” Part B, ed. by W. S. Trahanovsky, Academic Press, New York, 1973, pp. 1-95;
3. Y. Moro-oka and W. Ueda, Catalysis, 11, 223-245 (1994).
4. K. Friedrich and K. Wallenfels, in “The Chemistry of Cyano Group,” ed. by Z. Rappoport, Wiley Interscience, New York, 1970, pp. 67122.
5. J. V. Supniewski and P. L. Salzberg, Org. Synth. Coll. Vol. I, 1941, 46-47;
6. H. T. Clarke and R. R. Read, Org. Synth. Coll. Vol. I, 1941, 514-516;
7. W. Nagata and M. Yoshioka, Org. React., 25, 255-476 (1977);
8. C. M. Starks and C. Liotta, in “Phase Transfer Catalysis -Principals and Techniques,” Academic Press, New York, 1978, pp. 94-112;
9. M. North, Synlett, 1993, 807-820;
10. F. Effenberger, Angew. Chem. Int. Ed. Engl., 33. 1555-1556 (1994);
11. Y. Tsuji, N. Yamada, and S. Tanaka. J. Org. Chem., 58, 16-17 (1993).
12. H. Nernoto, Y. Kubota, and Y. Yamamoto, J. Org. Chem., 55, 4515-4516 (1990);
13. K. Inagaki, K. Nozaki, and H. Takaya, Synlett, 1997, 119-120.
14. D. B. Gerth and B. Giese, J. Org. Chem., 51, 3726-3729 (1986).
15. H. Yamada, Y. Asano, T. Hino, and Y. Tani, J. Ferment. Technol., 57, 8-14 (1979);
16. El. Yamada, Y. Asano, and Y. Tani, J. Ferment. Technol., 58, 495-500 (1980);
17. Y. Asano, Y. Tani, and H. Yamada, Agric. Biol. Chem., 44, 2251-2252 (1980);
18. Y. Asano, T. Yasuda, Y. Tani, and H. Yamada, Agric. Biol. Chem., 46, 1183-1189 (1982).
19. Y. Nakajima, T. Doi, Y. Satoh, A. Fujiwara, and I. Watanabe, Chem. Lett., 1987, 1767-1770;
20. Y. Sugiura, J. Kuwahara, T. Nagasawa, and H. Yamada, J. Am. Chem. Soc., 109,5848-5850 (1987);
21. T. Nagamune, J. Honda, W.-D. Cho, N. Kamiya, Y. Teratani, A. Hirata, H. Sasabe, and I. Endo, J. Mol. Biol., 220, 221-222 (1991);
22. M. Kobayashi and S. Shimizu, Kagaku to Seibutsu, 33, 479-483 (1995);
23. E. Dufour, A. C. Storer, and R. Menard, Biochemistry, 34, 16382-16388 (1995).
24. Y. Ashina and M. Suto, in “Development of an Enzymatic Process for Manufacturing Acrylamide and Recent Progress,” Marcel Dekker, Inc., 1992, pp. 91-107;
25. H. Yamada and M. Kobayashi, Biosci. Biotech. Biochem., 60, 1391-1400 (1996).
26. T. Nagasawa and H. Yamada, Yuki Gosei Kagaku Kyokaishi, 48, 1072-1073 (1990).
27. J. Crosby, J. Moilliet, J. S. Parratt, and N. J. Turner, J. Chem. Soc., Perkin Trans.1, 1994, 1679-1687.
28. P. Honicke-Schmidt and M. P. Schneider, J. Chem. Soc., Chem. Commun., 1990, 648-650.
29. M. A. Cohen, J. Sawden, and N. J. Turner, Tetrahedron Lett., 31, 7223-7226 (1990).
30. N. Klempier, A. de Raadt, K. Faber, and H. Griengl, Tetrahedron Lett., 32, 341-344 (1991).
31. M. S. Nawaz, T. M. Heinze, and C. E. Cerniglia, Appl. Environ. Microbiol., 58, 27-31 (1992).
32. A. de Raadt, N. Klempier, K. Faber, and H. Griengl, J. Chem. Soc., Perkin Trans.1, 1992, 137-140.
33. D. O’Grady and J. T. Pembroke, Biotechnol. Lett., 16, 47-50 (1994).
34. J. Mauger, T. Nagasawa, and H. Yamada, J. Biotechnol., 8, 87-95 (1988).
35. J. Mauger, T. Nagasawa, and H. Yamada, Tetrahedron, 45, 1347-1354 (1989).
36. H. Kakeya, N. Sakai, T. Sugai, and H. Ohta, Tetrahedron Lett., 32, 1343-1346 (1991).
37. K. Yamada, M. Ochiai, Y. Yotsumoto, Y. Morimoto, and Y. Teranishi, Eur. Pat. Appl. EP 579, 907 [Chem. Abstr., 120, 26461 lr (1994)].
38. R. Bauer, B. Hirrlinger, N. Layh, A. Stolz, and H.-J. Knackmuss, Appl. Microbiol. Biotechnol., 42, 1-7 (1994).
39. O. Meth-Cohn and M.-X. Wang, Tetrahedron Lett., 36, 9561-9564 (1995).
40. C. D. Mathew, T. Nagasawa, M. Kobayashi, and H. Yamada, Appl. Environ. Microbiol., 54, 1030-1032 (1988).
41. T. Nagasawa, C. D. Mathew, J. Mauger, and H. Yamada, Appl. Environ. Microbiol., 54, 1766-1769 (1988).
42. M. Kobayashi, N. Yanaka, T. Nagasawa, and H. Yamada, J. Antibiot., 43, 1316-1320 (1990).
43. Y. Takashima, F. Mukumoto, and S. Mitsuda, Eur. Pat. Appl. EP 666, 321 [Chem. Abstr., 123, 283760s (1995)].
44. N. Klempier, A. de Raadt, H. Griengl, and G. Heinisch, J. Heterocyclic Chem., 29, 93-95 (1992).
45. A. Kiener, R. Glockler, and K. Heinzmann, J. Chem. Soc., Perkin Trans1, 1993, 1201-1202.
46. S. Geresh, Y. Giron, Y. Gilboa, and R. Glaser, Tetrahedron, 49, 10099-10102 (1993).
47. K. Yamamoto, Y. Ueno, K. Otsubo, K. Kawakami, and K. Komatsu, Appl. Environ. Microbiol., 56, 3125-3129 (1990).
48. M. A. Cohen, J. S. Parratt, and N. J. Turner, Tetrahedron: Asymmetry, 3, 1543-1546 (1992).
49. T. Gilligan, H. Yamada, and T. Nagasawa, Appl. Microbiol. Biotechnol., 39, 720-725 (1993).
50. T. Beard, M. A. Cohen, J. S. Parratt, N. J. Turner, J. Crosby, and J. Moillet, Tetrahedron: Asymmetry, 4, 1085-1104 (1993).
51. F. Effenberger and J. Bohme, BioMed. Chem., 2, 715-721 (1994).
52. M. L. Gradley and C. J. Knowles, Biotechnol. Lett., 16, 41-46 (1994).
53. M. Takagi, K. Oishi, F. Ishimura, and I. Fujimatsu, J. Ferment. Bioeng., 78, 54-58 (1994).
54. M. Takagi, J. Shirokaze, K. Oishi, K. Otsubo, K. Yamamoto, N. Yoshida, and I. Fujimatsu, J. Ferment. Bioeng., 78, 191-193 (1994).
55. S. Matsutomo, A. Inoue, K. Kumagai, R. Murai, and S. Mitsuda, Biosci. Biotech. Biochem., 59, 720-722 (1995).
56. S. Mitsuda and H. Danda, Yuki Gosei Kagaku Kyokaishi, 54, 36-41 (1996).
57. K. Yamamoto, K. Otsubo, A. Matsuo, T. Hayashi, I. Fujimatsu, and K. Komatsu, Appl. Environ. Microbiol., 62, 152-155 (1996).
58. D. Bianchi, E. Battistel, P. Cesti, P. Golini, and R. Tassinari, Appl. Microbiol. Biotechnol., 40, 53-56 (1993).
59. K. Robins and T. Gilligan, Eur. Pat. Appl. EP 502, 525 [Chem. Abstr., 118, 37548r (1993)];
60. T. Zimmermann, K. Robins, O. M. Birch, and E. Boehlen, Eur. Pat. Appl. EP 524, 604 [Chem. Abstr., 118, 211426m (1993)].
61. Y. Fukuda, T. Harada, and Y. Izumi, J. Ferment. Technol, 51, 393-397 (1973).
62. K. Yamamoto, K. Oishi, I. Fujimatsu, and K. Komatsu, Appl. Environ. Microbiol., 57, 3028-3032 (1991).
63. H. Kakeya, N. Sakai, T. Sugai, and H. Ohta, Agric. Biol. Chem., 55, 1877-1881 (1991).
64. Y. Hashimoto, E. Kobayashi, T. Endo, M. Nishiyama, and S. Elorinouchi, Biosci. Biotech. Biochem., 60, 1279-1283 (1996).
65. A. J. J. Straathof, J. L. L. Rakels, and J. J. Heijnen, Biocatalysis, 4, 89-104 (1990).
66. U. Joeres and M. R. Kula, Appl. Microbiol. Biotechnol., 40, 599-605 (1994);
67. U. Joeres and M. R. Kula, Appl. Microbiol. Biotechnol., 40, 606-610 (1994).
68. S. K. Taylor, N. H. Chmiel, L. J. Simons, and J. R. Vyvyan, J. Org. Chem., 61, 9084-9085 (1996).
69. A. Arnaud, P. Galzy, and J. C. Jallageas, Bull. Soc. Chim. Fr., No. 2, 87-90 (1980).
70. A. M. Macadam and C. J. Knowles, Biotechnol. Lett., 7, 865 (1985).
71. S. Y. Choi and Y. M. Goo, Arch. Pharm. Res., 9, 45-47 (1986).
72. Y. Vo-Quang, D. Marais, L. Vo-Quang, F. Le Goffic, A. Thiery, M. Maestracci, A. Armaud, and P. Galzy, Tetrahedron Lett., 28, 4057-4060 (1987).
73. T. C. Bhalla, A. Miura, A. Wakamoto, Y. Ohba, and K. Furuhashi, Appl. Microbiol, Biotechnol., 37, 184-190 (1992).
74. J. Taillades, L. Garrel, F. Guillen, FI. Collet, and A. Commeyras, Bull. Soc. Chim. Fr., 132, 119-127 (1995).
75. H. F. M. Hermes, R. F. Tandler, T. Sonke, L. Dijkhuizen, and E. M. Meijer, Appl. Environ. Microbiol. 60, 153-159 (1994).
76. Y. Asano, A. Nakazawa, Y. Kato, and K. Kondo, J. Biol. Chem., 264, 14233-14239 (1989).
77. A. de Raadt, H. Griengl, N. Klempier, and A. E. Stutz, J. Org. Chem., 58, 3179-3184 (1993).
78. M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotech. Biochem., 60, 1540-1542 (1996).
79. M. Kobayashi, N. Yanaka, T. Nagasawa, and H. Yamada, Tetrahedron, 46, 5587-5590 (1990).
80. C. Bengis-Garber and A. L. Gutman, Appl. Microbiol. Biotechnol., 32, 11-16 (1989).
81. C. Bengis-Garber and A. L. Gutman, Tetrahedron Lett., 29, 2589-2590 (1988).
82. L. Martinkova, P. Olsovsky, E Prepechalova, and V. Kren, Biotechnol. Lett., 17, 1219-1222 (1995).
83. H. Nishise, M. Kurihara, and Y. Tani, Agric. Biol. Chem., 51, 2613-2616 (1987).
84. Y. Tani, M. Kurihara, H. Nishise, and K. Yamamoto, Agric. Biol. Chem., 53, 3143-3149 (1989).
85. K. Yamamoto, Y. Ueno, K. Otsubo, H. Yamane, K. Komatsu, and Y. Tani, J. Ferment. Bioeng., 73, 125-129 (1992).
86. H. Kakeya, N. Sakai, A. Sano, M. Yokoyama, T. Sugai, and H. Ohta, Chem. Lett., 1991, 1823-1824.
87. J. A. Crosby, J. S. Parratt, and N. J. Turner, Tetrahedron: Asymmetry, 3, 1547-1550 (1992).
88. A. Kerridge, J. S. Parratt, S. M. Roberts, F. Theil, N. J. Turner, and A. J. Willetts, BioMed. Chem., 2, 447-455 (1994).
89. M. Yokoyama, N. Imai, T. Sugai, and H. Ohta, J. Mol. Catal. Sect. B, Enzymatic, 1, 135-141 (1996).
90. M. Yokoyama, T. Sugai, and H. Ohta, Tetrahedron: Asymmetry, 4, 1081-1084 (1993).
91. M. Yokoyama, T. Sugai, and H. Ohta, Abstract of Papers, 65th Annual Meeting of Chemical Society of Japan, 4G211, Tokyo, March 1993.
92. L. M. Ciskanik, J. M. Wilczek, and R. D. Fallon, Appl. Environ. Microbiol., 61, 998-1003 (1995).
93. K. Yamamoto and K. Komatsu, Agric. Biol. Chem., 55, 1459-1466 (1991).
94. H. Ohta, Chimia, 50, 434-436 (1996).
95. H. Ohta, Kagaku to Kogvo(Chemistry and Industry, the Chemical Society of Japan), 50, 977-979 (1997).
96. H. P. Deigner, C. Blencowe, and C. E. Freyberg, J. Mol. Catal. Sect. B, Enzymatic, 1, 61-70 (1996).
97. T. Sugai, O. Katoh, and H. Ohta, Tetrahedron, 51, 11987-11998 (1995).
98. T. Sugai, M. Yokoyama, T. Yamazaki, and H. Ohta, Chem. Lett., 1997, 797-798.
99. R. V. A. Orru, W. Kroutil, and K. Faber, Tetrahedron Lett., 38, 1753-1754 (1997).
100. Y. Ohtsuka, O. Katoh, T. Sugai, and H. Ohta, Bull, Chem. Soc., Jpn., 70, 483-491 (1997).
101. S. J. Maddrell, N. J. Turner, A. Kerridge, A. J. Willetts, and J. Crosby, Tetrahedron Lett., 37, 6001-6004 (1996).
102. Examples: Rhodococcus equi strain A4: correspondence to Dr. Ludmila Martinkova, Institute of Microbiology, Academy of Sciences of the Czech Republic, Videnska 1083, CZ-142 20 Prague 4, Czech Republic. Brevibacterium R312 (renamed as a Rhodococcus sp., CBS 717-73): from Centraalbureau voor Schimmel cultures, Baarn, The Netherlands. Rhodococcus rhodochrous IFO 15564: Institute for Fermentation, Osaka (IFO), 2-17-85
103. Juso-honmachi, Yodogawa-ku, Osaka 532, Japan. Some other strains are available from ATCC and NCI.