Synthesis of chiral pharmaceutical intermediates by oxidoreductases

ACS Symposium Series

Volumn 776, Issue , 2001, Pages 216-247

  Patel, Ramesh N ^a   Hanson, Ronald L ^a  

^a Bristol Myers Sauibb P   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041916079     PISSN: 00976156     EISSN: None     Source Type: Book Series    
DOI: 10.1021/bk-2001-0776.ch015     Document Type: Article

References (77)

1. Sih, C. J., and Chen, C. S. Angew. Chem.Int. Engl.23, 1984, 570-578.
2. Jones, J. B. Enzymes in organic synthesis. Tetrahedron, 1986, 42, 3351-3403.
3. Csuz, R. and Glanzer, B. I.. Chem. Rev. 1991, 91, 49-97.
4. Crosby, J. Tetrahedron. 47, 1991, 4789-4846.
5. Simon, H., Bader, J., Gunther, H., Neumann, S., and Thanos, J. Angew. Chem. Int. Engl. 1985, 24, 539-553.
6. Stinson, S. C. Chiral drugs. Chem. Eng. News, Sept. 28. 1992, 46-79.
7. Santaneillo, E., Ferraboschi, P., Grisenti, P., and Manzocchi, A. Chem. Rev. 1992, 92, 1071-1140.
8. Margolin, A. L. Enzyme. Microb. Technol. 1993, 15, 266-280 (1993).
9. Wong, C-H and Whitesides, G. M. Tetrahedron Organic Chemistry Series, 1992, 12. Pergamon, Elsevier Science Ltd. USA. (1994).
10. Patel, R. N., Banerjee, A., Liu, M., Hanson, R. L., Ko, R. Y., Howell, J. M., and Szarka, L. J. Biotechnol. Appl. Biochem. 1993, 17, 139-153.
11. Patel, R. N., Banerjee, A., Mc Namee, C. J., and Szarka, L. J. Appl. Microbiol Biotechnol. 1993,40, 241-245.
12. Hanson, R. L., Singh, J., Kissick, T. P. , Patel, R. N., Szarka, L. J., and Mueller, R. H. Bioorg. Chem. 18, 1990, 116-130.
13. Hanson, R. L., Bembenek, K. S., Patel, R. N., and Szarka, L. J. Appl. Microbiol. Biotechnol., 1992, 37, 599-603.
14. Ferris, C. D., D. J. Hirsch, B. P. Brooks, and S. H. Snyder. J. Neurochemistry., 1991, 57, 729-737.
15. Junien, J. L. and B. E. Leonard. Clinical Neuropharmacolog., 1989, 12: 353-374.
16. Martin, W. R., C. G. Eades, J. A. Thompson, R. E. Huppter, and P. E. Gilbert. J. Pharmacol. Exp. Ther. 1976, 197, 517-539.
17. Walker, J. M., W. D. Bower, F. O. Walker, R. R. Matsumoto, B. D. Costa, and K. C. Rice. Pharm. Reviews. 1992, 42, 355-402.
18. Steinfels, G. F., S. W. Tam, and L. Cook. Neureopsychopharmacology. 1989, 2: 201-207.
19. Massamiri, T., and S. P. Duckies. J. Pharmacology and Experimental Therapeutics. 1990, 253, 124-129 (1990).
20. Martinez, J. A. and L. Bueno. European J. Pharmacology. 1991, 202: 379-383.
21. Taylor, D. P., M. S. Eison, S. L. Moon, and F. D. Yocca.. Adv. Neuropsy. Psychopharm. 1991, 1: 307-315.
22. Yevich, J. P., W. G. Lobeck. 1986. U.S. Patent # 4605655.
23. Yevich, J. P., J. S. New, D. W. Smith. J. Med. Chem. 1986, 29: 359-369.
24. Bradford, M. M. Anal. Biochem.1976, 72, 248-254.
25. Larsen, A. A., and Lish P. M. Nature.1964, 203- 1283-1284.
26. Uloth, R. H., Kirk, J. R., Gould, W. A., and Larsen, A. A. J. Med. Chem. 1966, 9, 88-96.
27. Lish, P.A., Weikel, J. H, and Dungan K. W. J. Pahrma and Exper. Therapeutics. 1965, 149, 161-173.
28. Somani, P., and Bachand, T. Eur. J. Pharma, 1969, 7, 239-247.
29. Karanewsky, D.S., Badia, M. C., Cushman, D. W., DeForrest, J. M. Dejneka, T., Loots, M. J., Perri, M. G., Petrillo, E. W. Jr., and Powell, J. R.. J. Med. Chem. 1988, 31, 204-212.
30. Haskell, T. H., Rodebaugh, R., Plessas, N., Watson, D., and Westland, R. D. Carbohyd. Res. 1973, 25,263-280.
31. Meister, A. J. Biol. Chem. 1954, 206, 577-585.
32. Robison, R. S., Doremus, M. G. and Szarka, L. J., unpublished results
33. Kusakabe, H., Kodama, K., Kuninaka, A., Yoshino, H., Misono, H., and Soda, K. J. Biol. Chem. 1980, 255, 976-981 .
34. Schütte, H., Hummel, W., and Kula, M. R.. Appl. Microbiol. Biotechnol. 1984, 19,167-176.
35. Pelmont, J., Arlaud, G., and Rossat, A. M. Biochimie. 1972, 54, 1359-1374.
36. Duerre, J. A. and Chakrabarty, S. J. Bacteriol. 1975, 727, 656-663.
37. Williams, R. M. In Synthesis of Optically Active a-amino Acids. (Baldwin, J. E. and Magnus, P. D. Eds.) 1989, vol. 7, Pergamon, Oxford/ New York.
38. Kamphuis, J., Boesten, W. H., Broxterman, Q. B., Hermes, H. F. M., van Balken, J. A. M. Meijer, E. M., and Shoemaker, H. E. Adv. in Biochem. Engin. Biotechnol. 1992, 42, 134-186.
39. Sykes, R. B., Cimarusti, C. M., Bonner, D. P., Bush, K., Floyd, D. M., Georgopadakou, N. H., Koster, W. H., Liu, W. C., Parker, W. L., Principle, P. A., Rathnum, M. L., Slusarchyk, W. A., Trejo, W. H., and Wells, J. S. Nature (London) 291, 489-491.
40. Parker, W. L., O'sullivan, J., and Sykes, R. B. Adv. Appl. Microbiol. 1986, 31, 181-205.
41. Roemmele, R. C. and Rapoport, H. J. Org. Chem. 1989, 54, 1866-1875.
42. Ito, Y., Sawamura, M., Shirakawa, E., Hayashizaki, K., and Hayashi, T. Tetrahedron. 44, 5253-5262.
43. Guanti, G., Banfi, L., and Narisano, E. Tetrahedron. 1988, 44, 5553-5562.
44. Evans, D. A., Sjogren, E. B., Weber, A. E., and Conn, R. E.Tetrahedron Lett. 1987, 28, 39-42.
45. Gordon, E. M., Ondetti, M. A., Pluscec, J., Cimarusti, C. M., Bonner, D. P., and Sykes, R. B. J. Amer. Chem. Soc. 1982, 104, 6053-6060.
46. Parker, W. L., Cohen, E. M., and Koster, W. H. 1988, US Patent 474122.
47. Slusarchyk, W. A., Dejneka, T., Gougoutas, J. Z., Koster, W. H., Kronenthal, D. R., Malley, M. F., Perri, M. G., Routh, F. L., Sundeen, J. E., Weaver, E. R., Zahler, R., Godfrey, J. D., Mueller, R. H., and Langen, D. J. Tetrahedron Lett. 27, 2789-2792.
48. Godfrey, J. D., Mueller, R. H., and Van Langen, D. J. Tetrahedron Lett. 27, 2793-2796.
49. Edwards, G. W. and Minthorn, M. L. Jr. Canad. J. Biochem. 1968, 46, 1227-1230.
50. Berse, C. and Bessette, P. Canad. J. Chem. 1971, 49, 2610-2611.
51. Beyerman, H. C., Maat, L., De Rijke, D., and Visser, J. P. Red. Trav. Chim. Pays-Bas. 1967, 86, 1057-1060.
52. Schollkopf, U., Nozulak, J., and Groth, U. Synthesis, 1982, 868-870.
53. Wiechmann, R., Wandrey, C., Buckmann, A. F., and Kula, M-R. Biotechnol. Bioeng. 1981, 23, 2789-2802.
54. Schutte, H., Hummel, W., Tsai, H., and Kula, M. Appl. Microbiol. Biotechnol. 1985, 22, 306-317.
55. Monot, F., Benoit, Y., Lemal, J., Honorat, A., and Ballerini, D. In Proc. Eur.Cong. Biochem. (Neijssel, O. M., van der Meer, R. R., and Luyben, K. C. A. M. Eds.) 1987, vol. 2, pp. 42-45, Elsevier, Amsterdam. (1987).
56. Oshima, T., Misono, H., and Soda, K. J. Biol. Chem. 1978, 253, 5719-5725.
57. Robl, J. A.; Sun, C; Stevenson, J;, Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T; Slusarchyk, W. A.; Chao, S; Stratton, L.; Misra, R. N. ; Bednarz, M. S.; Asaad, M.M.; Cheung, H. S.; Aboa-Offei, B. E.; Smith, P.L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577.
58. Robl, J. A.; Cimarusti, M.P. Tetrahedron Letters. 1994, 35, 1393-1396.
59. Maurer, P. J.; Miller, M. J. J. Org. Chem. 1981, 46, 2835-2836.
60. Maurer, P.J.; Miller, M. J. J. Am. Chem. Soc. 1982,104, 3096-3101.
61. Maurer, P.J.; Miller, M. J. J. Am. Chem. Soc. 1983, 105, 240-245.
62. Culvenor, C.C. J.; Foster, M. C.; Hegarty, M.P. Aust. J. Chem. 1971, 24, 371-375.
63. Bodanszky, M; Martinez, J.; Priestly, G. P.; Gardner, J. D.; Mutt, V. J. Med. Chem. 1978, 21, 1030-1037.
64. Dreyfuss, P. J. Med. Chem. 1974, 17, 252-257.
65. Kern, B. A.; Reitz, R. H. Agric. Biol. Chem. 1978, 42, 1275.
66. Bommarius, A. S. In Enzyme Catalysis in Organic Synthesis:; Drauz, K. and Waldmann, H., Ed.; VCH: Weinheim, 1995; Vol II, pp 633-641 and cited references.
67. Galkin, A.; Kulakova, L.; Yoshimura, T.; Soda, K.; Esaki, N. Appl. Environ. Microbiol. 1997, 63, 4651-4655.
68. Rumbero, A., Martin, J. C., Lumbreras, M. A., Liras, P. and Esmahan, C. Bioorg. Med. Chem. 1995, 3, 1237-1240
69. Kula, M. R. and Wandrey, C. Methods in Enzymology 1987, 136, 9-21.
70. Hanson, R. L., Schwinden, M. D., Banerjee, A., Brzozowski, D. B., Chen, B-C., Patel, B. P., McNamee, C. G., Kodersha, G. A., Kronenthal, D. R., Patel, R. N. and Szarka, L. J. J. Bioorg. Med. Chem. 1999, 7, 2247-2252.
71. Hanson, R. L.; Howell, J.; LaPorte, T.; Donovan, M-J.; Cazzulino, D.; Zannella, V.; Montana, M.; Nanduri, V.; Scwartz, S.; Eiring R.; Durand, S.; Wasylyk, J.; Parker, L.; Liu, M.; Okuniewicz, F.; Chen, B-J, Harris, J.; Natalie, K.; Ramig, K.; Swaminathan, S.; Rosso, V.; Pack, S.; Lotz, B.; Bernot, P.; Rusowicz, A.; Lust D.; Tse, K.; Venit, J.; Szarka, L.; Patel, R. N. Enzyme Microbial Technol.(in press).
72. Schütte, H. Flossdorf, J. Sahm, H. and Kula, M-R. Eur. J. Biochem. 1976, 62, 151-160.
73. Hou, C. T., Patel, R. N., Laskin, A. I. and Barnabe, N. Arch. Biochem. Biophys. 1982, 216, 296-305
74. Ohshima, T.; Takada, H.; Yoshimura, T.; Esaki, N.; Soda, K. J. Bacteriol. 1991, 173, 3943-3948.
75. Ohshima, T.; Nishida N.; Bakthavatsalam, S.; Kataoka, K.; Takada, H.; Yoshimura, T.; Esaki, N.; Soda, K. Eur. J. Biochem. 1994, 222, 305-309.
76. Ohshima, T., Sugimoto, H. and Soda, K. Anal Lett 1988, 21, 2205-2215.
77. Shaked, Z. and Whitesides, G. M. J. Am. Chem. Soc. 1980, 102, 7104-7105.