A novel approach to enantiopure cyclopropane compounds from biotransformation of nitriles

New Journal of Chemistry

Volumn 26, Issue 11, 2002, Pages 1575-1583

  Wang, Mei Xiang ^a   Feng, Guo Qiang ^a  

^a Institute of Chemistry   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDASE; CYCLOPROPANE DERIVATIVE; NITRILE; NITRILE HYDRATASE;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; PRIORITY JOURNAL;

EID: 0036431768     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b200110a     Document Type: Article

References (74)

1. (a) C.-H. Wong and G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Pergamon Press, Oxford, 1994;
2. (b) K. Drauz and H. Waldmann, Enzyme Catalysis in Organic Chemistry, VCH, Weinheim, 1995;
3. (c) K. Faber, Pure Appl. Chem., 1997, 69, 1613;
4. (d) H.-J. Rehm and G. Reed, Biotechnology, Wiley-VCH, Weinheim, 1998, vol. 8a;
5. (e) W.-D. Fessner, Biocatalysis: From Discovery to Application, Springer Verlag, Berlin and Heidelberg, 1999
6. (a) J. B. Jones, Aldrichim. Acta, 1993, 26, 105;
7. (b) E. Schoffers, A. Golebiowski and C. R. Johnson, Tetrahedron, 1996, 52, 3769.
8. (a) T. Sugai, T. Yamazaki, M. Yokoyama and H. Ohta, Biosci., Biotechnol., Biochem., 1997, 61, 1419;
9. (b) J. Crosby, J. Moiliet, J. S. Parratt and N. J. Turner, J. Chem. Soc., Perkin Trans. 1, 1994, 1679.
10. Recent examples of biotransformation of nitriles (a) J. E. Gavagan, S. K. Fager, R. D. Fallon, P. W. Folsom, F. E. Herkes, A. Eisenberg, E. C. Hann and R. DiCosmo, J. Org. Chem., 1998, 63, 4792; (b) K. Matoishi, A. Sano, N. Imai, T. Yamazaki, M. Yokoyama, T. Sugai and H. Ohta, Tetrahedron: Asymmetry, 1998, 9, 1097; (c) F. Effenberger and B. W. Graef, J. Biotechnol., 1998, 60, 165; (d) M. A. Wegman, U. Heinemann, A. Stolz, F. van Rantijk and R. A. Sheldon, Org. Process Res. Dev., 2000, 4, 318; (e) F. B. Cooling, S. K. Fager, R. D. Fallon, P. W. Folsom, F. G. Gallagher, J. E. Gavagan, E. C. Hann, F. E. Herkers, R. L. Phillips, A. Sigmund, I. N. Wanger, W. Wu and R. DiCosmo, J. Mol. Catal. B: Enzym., 2001, 11, 295.
11. Recent examples of biotransformation of nitriles (a) J. E. Gavagan, S. K. Fager, R. D. Fallon, P. W. Folsom, F. E. Herkes, A. Eisenberg, E. C. Hann and R. DiCosmo, J. Org. Chem., 1998, 63, 4792; (b) K. Matoishi, A. Sano, N. Imai, T. Yamazaki, M. Yokoyama, T. Sugai and H. Ohta, Tetrahedron: Asymmetry, 1998, 9, 1097; (c) F. Effenberger and B. W. Graef, J. Biotechnol., 1998, 60, 165; (d) M. A. Wegman, U. Heinemann, A. Stolz, F. van Rantijk and R. A. Sheldon, Org. Process Res. Dev., 2000, 4, 318; (e) F. B. Cooling, S. K. Fager, R. D. Fallon, P. W. Folsom, F. G. Gallagher, J. E. Gavagan, E. C. Hann, F. E. Herkers, R. L. Phillips, A. Sigmund, I. N. Wanger, W. Wu and R. DiCosmo, J. Mol. Catal. B: Enzym., 2001, 11, 295.
12. Recent examples of biotransformation of nitriles (a) J. E. Gavagan, S. K. Fager, R. D. Fallon, P. W. Folsom, F. E. Herkes, A. Eisenberg, E. C. Hann and R. DiCosmo, J. Org. Chem., 1998, 63, 4792; (b) K. Matoishi, A. Sano, N. Imai, T. Yamazaki, M. Yokoyama, T. Sugai and H. Ohta, Tetrahedron: Asymmetry, 1998, 9, 1097; (c) F. Effenberger and B. W. Graef, J. Biotechnol., 1998, 60, 165; (d) M. A. Wegman, U. Heinemann, A. Stolz, F. van Rantijk and R. A. Sheldon, Org. Process Res. Dev., 2000, 4, 318; (e) F. B. Cooling, S. K. Fager, R. D. Fallon, P. W. Folsom, F. G. Gallagher, J. E. Gavagan, E. C. Hann, F. E. Herkers, R. L. Phillips, A. Sigmund, I. N. Wanger, W. Wu and R. DiCosmo, J. Mol. Catal. B: Enzym., 2001, 11, 295.
13. Recent examples of biotransformation of nitriles (a) J. E. Gavagan, S. K. Fager, R. D. Fallon, P. W. Folsom, F. E. Herkes, A. Eisenberg, E. C. Hann and R. DiCosmo, J. Org. Chem., 1998, 63, 4792; (b) K. Matoishi, A. Sano, N. Imai, T. Yamazaki, M. Yokoyama, T. Sugai and H. Ohta, Tetrahedron: Asymmetry, 1998, 9, 1097; (c) F. Effenberger and B. W. Graef, J. Biotechnol., 1998, 60, 165; (d) M. A. Wegman, U. Heinemann, A. Stolz, F. van Rantijk and R. A. Sheldon, Org. Process Res. Dev., 2000, 4, 318; (e) F. B. Cooling, S. K. Fager, R. D. Fallon, P. W. Folsom, F. G. Gallagher, J. E. Gavagan, E. C. Hann, F. E. Herkers, R. L. Phillips, A. Sigmund, I. N. Wanger, W. Wu and R. DiCosmo, J. Mol. Catal. B: Enzym., 2001, 11, 295.
14. Recent examples of biotransformation of nitriles (a) J. E. Gavagan, S. K. Fager, R. D. Fallon, P. W. Folsom, F. E. Herkes, A. Eisenberg, E. C. Hann and R. DiCosmo, J. Org. Chem., 1998, 63, 4792; (b) K. Matoishi, A. Sano, N. Imai, T. Yamazaki, M. Yokoyama, T. Sugai and H. Ohta, Tetrahedron: Asymmetry, 1998, 9, 1097; (c) F. Effenberger and B. W. Graef, J. Biotechnol., 1998, 60, 165; (d) M. A. Wegman, U. Heinemann, A. Stolz, F. van Rantijk and R. A. Sheldon, Org. Process Res. Dev., 2000, 4, 318; (e) F. B. Cooling, S. K. Fager, R. D. Fallon, P. W. Folsom, F. G. Gallagher, J. E. Gavagan, E. C. Hann, F. E. Herkers, R. L. Phillips, A. Sigmund, I. N. Wanger, W. Wu and R. DiCosmo, J. Mol. Catal. B: Enzym., 2001, 11, 295.
15. Z. Rappoport, The Chemistry of the Cyano Group, Wiley Interscience, New York, 1970.
16. (a) D. Evgred and S. Harnett, Cyanide compounds in biology (Ciba Foundation Symposium 140), Wiley, Chichester, 1988;
17. (b) J.-C. Jallegeas, A. Arnaud and P. Galzy, Adv. Biochem. Eng., 1980, 12, 1;
18. (c) J. L. Legras, G. Chuzel, A. Arnaud and P. Galzy, World J. Microbiol. Biotechnol., 1990, 6, 83.
19. (a) D. B. Harper, Biochem. Soc. Trans., 1976, 4, 502;
20. (b) D. B. Harper, Biochem. J., 1977, 165, 309;
21. (c) M. Kobayashi and S. Shimizu, FEMS Microbiol. Lett., 1994, 120, 217.
22. (a) Y. Asano, Y. Tani and H. Yamada, Agric. Biol. Chem., 1980, 44, 2251;
23. (b) Y. Asano, K. Fujishiro, Y. Tani and H. Yamada, Agric. Biol. Chem., 1982, 46, 1165;
24. (c) Y. Asano, M. Tachibana, Y. Tani and H. Yamada, Agric. Biol. Chem., 1982, 46, 1175.
25. For a useful overview, see: O. Meth-Cohn and M.-X. Wang, J. Chem. Soc., Perkin Trans. 1, 1997, 1099 and references cited therein.
26. For a useful overview, see: O. Meth-Cohn and M.-X. Wang, J. Chem. Soc., Perkin Trans. 1, 1997, 3197 and references cited therein.
27. M. Kobayashi and S. Shimizu, Curr. Opin. Chem. Biol., 2000, 4, 95.
28. (a) T. Nagasawa, S. Schimizu and H. Yamada, Appl. Microbiol. Biotechnol., 1993, 40, 189;
29. (b) M. Kobayashi, T. Nagasawa and H. Yamada, Trends Biotechnol., 1992, 40, 189.
30. A. J. Blakey, J. Colby, E. Williams and C. O'Reilly, FEMS Microbiol. Lett., 1995, 129, 57.
31. M.-X. Wang, G. Lu, G.-J. Ji, Z.-T. Huang, O. Meth-Cohn and J. Colby, Tetrahedron: Asymmetry, 2000, 11, 1123.
32. M.-X. Wang, J.-J. Li, G.-J. Ji and J. S. Li, J. Mol. Catal. B: Enzym., 2001, 14, 77.
33. M.-X. Wang and S.-J. Lin, Tetrahedron Lett., 2001, 42, 6925.
34. (a) M.-X. Wang, C.-S. Liu, J.-S. Li and O. Meth-Cohn, Tetrahedron Lett., 2000, 41, 8549;
35. (b) M.-X. Wang, C.-S. Liu and J.-S. Li, Tetrahedron: Asymmetry, 2001, 12, 3367.
36. Part of this work has appeared as a preliminary communication: M.-X. Wang and G.-Q. Feng, Tetrahedron Lett., 2000, 41, 6501.
37. (a) M. P. Doyle and D. C. Forbes, Chem. Rev., 1998, 98, 911;
38. (b) M. P. Doyle and M. N. Protopopova, Tetrahedron, 1998, 54, 7919;
39. (c) V. K. Singh, A. D. Gupta and G. Sekar, Synthesis, 1997, 137;
40. (d) M. Lautens, W. Klute and W. Tam, Chem. Rev., 1996, 96, 49.
41. (a) C. Kaiser, B. M. Lester, C. L. Zirkle, A. Burger, C. S. Davis, T. J. Della and L. Zirngibl, J. Med. Pharm. Chem., 1962, 5, 1243;
42. (b) C. L. Zirkle, C. Kaiser, D. H. Tedeschi, R. E. Tedeschi and A. Burger, J. Med. Pharm. Chem., 1962, 5, 1265.
43. L.-E. Arvidsson, J. L. G. Johansson, K. Svensson, S. Hjorth, T. Magnusson, A. Carlsson, P. Lindberg, B. Andersson, D. Sanchez, H. Wikstrom and S. Sundell, J. Med. Chem., 1988, 31, 92.
44. H. Nozaki, S. Moriuti, H. Takaya and R. Noyori, Tetrahedron Lett., 1966, 5239.
45. T. Aratani, Pure Appl. Chem., 1985, 57, 1839.
46. (a) D. Müller, G. Umbricht, B. Weber and A. Pfaltz, Helv. Chim. Acta, 1991, 74, 232;
47. (b) U. Leutenegger, G. Umbricht, C. Fahrni, P. von Matt and A. Pfaltz, Tetrahedron, 1992, 48, 2143;
48. (c) A. Pfaltz, Acc. Chem. Res., 1993, 26, 339.
49. (a) R. E. Lowenthal, A. Abiko and S. Masamune, Tetrahedron Lett., 1990, 31, 6005;
50. (b) R. E. Lowenthal and S. Masamune, Tetrahedron Lett., 1991, 32, 7373.
51. (a) D. A. Evans, K. A. Woerpel, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726;
52. (b) D. A. Evans, K. A. Woerpel and M. J. Scott, Angew. Chem., Int. Ed. Engl., 1992, 31, 430.
53. (a) T. Uchida, R. Irie and T. Katsuki, Tetrahedron, 2000, 56, 3501;
54. (b) T. Niimi, T. Uchida, R. Irie and T. Katsuki, Tetrahedron Lett., 2000, 41, 3647.
55. R. Csuk, M. J. Schabel and Y. von Scholz, Tetrahedron: Asymmetry, 1996, 7, 3505.
56. S. C. Stinton, Chem. Eng. News, 1994, 72, 38.
57. (a) C. Kaiser, B. M. Trost, J. Beeson and J. Weinstock, J. Org. Chem., 1965, 30, 3972;
58. (b) C. R. Johnson and P. Rogers, J. Org. Chem., 1973, 38, 1793.
59. J. H. Hall and M. Gisler, J. Org. Chem., 1976, 41, 3769.
60. (a) H. Kakeya, N. Sakai, T. Sugai and H. Ohta, Tetrahedron Lett., 1991, 32, 1343;
61. (b) F. Effenberger and J. Böhme, Bioorg. Med. Chem., 1994, 2, 715;
62. (c) M. A. Cohen, J. S. Parratt and N. J. Turner, Tetrahedron: Asymmetry, 1992, 3, 1543;
63. (d) T. Beard, M. A. Cohen, J. S. Parratt, N. J. Turner, J. Crosby and J. Moilliet, Tetrahedron: Asymmetry, 1993, 4, 1085.
64. (a) U. M. Teotino, D. D. Bella, A. Gandini and G. Benelli, J. Med. Chem., 1967, 10, 1091;
65. (b) J. Vallgarda, U. Appelberg, L.-E. Arvidsson, S. Hjorth, B. E. Svensson and U. Hacksell, J. Med. Chem., 1996, 39, 1485.
66. R. F. Borne, M. L. Forrester and I. W. Waters, J. Med. Chem., 1977, 20, 771.
67. A. Solladie-Cavallo and T. Isarno, Tetrahedron Lett., 1999, 40, 1579.
68. G. A. Pinna, M. Loruga, G. Paglietti and G. Cignarella, Farmaco, 1980, 35, 684.
69. S. C. Yasui and T. A. Keiderling, J. Am. Chem. Soc., 1987, 109, 2311.
70. T. A. Wittstruck and E. N. Trachtenberg, J. Am. Chem. Soc., 1967, 89, 3810.
71. T. J. W. Jorden and G. W. Perold, Chem. Ber., 1953, 86, 991.
72. R. Fuchs, C. A. Kaplan, J. J. Bloomfield and L. F. Hatch, J. Org. Chem., 1962, 27, 733.
73. T. Aratani, Y. Nakanisi and H. Nozaki, Tetrahedron, 1970, 26, 1675.
74. W. E. Doering and E. A. Barsa, Tetrahedron Lett., 1978, 2495.