Selectivity of the biooxygenation of N-phenylcarbamates by the fungus Beauveria bassiana

Tetrahedron

Volumn 53, Issue 50, 1997, Pages 17067-17078

  Pietz, Sylke ^a   Wölker, Dörthe ^a   Haufe, Günter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBANILIC ACID DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; FUNGUS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXYGENATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

BASSIANA; BEAUVERIA; CORDYCEPS BASSIANA; FUNGI;

EID: 0343488494     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10148-X     Document Type: Article

References (67)

1. (a) G. S. Fonken, M. E. Herr, H. C. Murray, L. M. Reineke, J. Am. Chem. Soc. 1967, 89, 672.
2. (b) R. A. Johnson, M. E. Herr, H. C. Murray, G. S. Fonken, J. Org. Chem. 1968, 33, 3217.
3. (c) G. S. Fonken, R. A. Johnson, Chemical Oxidations with Microorganisms, Marcel Dekker, New York, 1972.
4. (a) K. Kieslich, Bull. Soc. Chim. France 1980, 9; L. L. Smith, in Biotechnology, H.-J. Rehm, G. Reed, Eds., Vol 6a, K. Kieslich, Ed., VCH, Weinheim, 1984, pp 31-78.
5. (a) K. Kieslich, Bull. Soc. Chim. France 1980, 9; L. L. Smith, in Biotechnology, H.-J. Rehm, G. Reed, Eds., Vol 6a, K. Kieslich, Ed., VCH, Weinheim, 1984, pp 31-78.
6. (b) H. L. Holland, Acc. Chem. Res. 1984, 17, 398.
7. (c) V. Krasnobaew, in Biotechnology, H.-J. Rehm, G. Reed, Eds., Vol 6a, K. Kieslich, Ed., VCH, Weinheim, 1984, pp 97-125; A. Kergomard, ibid, pp 127-205.
8. (c) V. Krasnobaew, in Biotechnology, H.-J. Rehm, G. Reed, Eds., Vol 6a, K. Kieslich, Ed., VCH, Weinheim, 1984, pp 97-125; A. Kergomard, ibid, pp 127-205.
9. (d) H. L. Holland, Organic Synthesis with Oxidative Enzymes, VCH, New York, 1992; R. Azerad, Chimia 1993, 47, 93.
10. (d) H. L. Holland, Organic Synthesis with Oxidative Enzymes, VCH, New York, 1992; R. Azerad, Chimia 1993, 47, 93.
11. (e) J. M. Fang, C. H. Lin, C. W. Bradshaw, C. H. Wong, J. Chem. Soc., Perkin Trans. 1, 1995, 967.
12. (f) W. R. Abraham, H. A. Arfmann, B. Stumpf; P. Washausen, K. Kieslich, Bioflavour '87, P. Schreier, Ed., de Gruyter, Berlin, 1988, pp 399-427.
13. Recently Cunninghamella blakesleeana and Bacillus megaterium have been used extensively for biotransformation of 2-cycloalkylbenzoxazoles: (a) A. de Raadt, H. Griengl, M. Petsch, P. Plachota, N. Schoo, H. Weber, G. Braunegg, I. Kopper, M. Kreiner, A. Zeiser, K. Kieslich, Tetrahedron:Asymmetry, 1996, 7, 467.
14. (b) A. de Raadt, H. Griengl, M. Petsch, P. Plachota, N. Schoo, H. Weber, G. Braunegg, I. Kopper, M. Kreiner, A. Zeiser, Tetrahedron:Asymmetry, 1996, 7, 473.
15. (c) A. de Raadt, H. Griengl, M. Petsch, P. Plachota, N. Schoo, H. Weber, G. Braunegg, I. Kopper, M. Kreiner, A. Zeiser, Tetrahedron:Asymmetry, 1996, 7, 491.
16. Previously known as Sporotrichum sulfurescens. For reclassification as Beauveria sulfurescens see: J. Taylor, J. Mycology 1970, 62, 797. This microorganism is currently listed as Beauveria bassiana ATCC 7159 in the catalog of the American Type Culture Collection.
17. (a) J. D. Fourneron, A. Archelas, R. Furstoss, J. Org. Chem. 1989, 54, 2478.
18. (b) Y. Hu, R. J. Highet, D. Marion, H. Ziffer, J. Chem. Soc., Chem. Comm. 1991, 1176.
19. (c) R. A. Johnson, M. E. Herr, H. C. Murray, C. G. Chidester, F. Han, J. Org. Chem. 1992, 57, 7209.
20. (d) N. Floyd, F. Munyemana, S. M. Roberts, A. J. Willetts, J. Chem. Soc., Perkin Trans. 1 1993, 881.
21. (a) M. E. Herr, R. A. Johnson, W. C. Krueger, H. C. Murray, L. M. Pschigoda, J. Org. Chem. 1970, 35, 3607.
22. (b) A. Archelas, J.-D. Fourneron, R. Furstoss, J. Org. Chem. 1988, 53, 1797.
23. (c) R. A. Johnson, M. E. Herr, H. C. Murray, W. C. Krueger, L. M. Pschigoda, D. J. Duchamp, J. Org. Chem. 1992, 57, 7212.
24. (d) C. R. Davis, R. A. Johnson, J. I. Cialdella, W. F. Liggett, S. A. Mizsak, F. Han, V. P. Marshall, J. Org. Chem. 1997, 62, 2252.
25. (e) C. R. Davis, R. A. Johnson, J. I. Cialdella, W. F. Liggett, S. A. Mizsak, V. P. Marshall, J. Org. Chem. 1997, 62, 2244.
26. (a) O. Reiser, Angew. Chem. 1994, 106, 73; Angew. Chem., Int. Ed. Engl. 1994, 33, 69.
27. (a) O. Reiser, Angew. Chem. 1994, 106, 73; Angew. Chem., Int. Ed. Engl. 1994, 33, 69.
28. (b) D. Ostovic, T. C. Bruice, Acc. Chem. Res. 1992, 25, 314.
29. (c) D. H. R. Barton, D. Doller, Acc. Chem. Res., 1992, 25, 504.
30. (d) D. H. R. Barton, S. D. Béviére, W. Chavasiri, E. Csuhai, D. Doller, W.-G. Lui, J. Am. Chem. Soc. 1992, 114, 2147.
31. (e) J. A. Davis, P. L. Watson, J. F. Liebmann, A. Greenberg, Selective Hydrocarbon Activation, VCH Publishers, New York, 1990.
32. (f) C. L. Hill, Activation and Funktionalisation of Alkanes, Wiley, New York, 1989.
33. (g) A. V. Shilov, Activation of Saturated Hydrocarbons by Transition Metal Complexes, Reisel, Boston, 1984.
34. P. R. Ortiz de Montellano, Cytochrome P-450, Mechanism and Biochemistry, 2nd ed. Plenum Press, New York 1995.
35. R. A. Johnson, M. E. Herr, H. C. Murray, G. S. Fonken, J. Org. Chem. 1970, 35, 622 and references cited therein,
36. (b) M. E. Herr, H. C. Murray, G. S. Fonken, J. Med. Chem. 1971, 14, 842.
37. R. A. Johnson, M. E. Herr, H. C. Murray, L. M. Reineke, J. Am. Chem. Soc. 1971, 22, 4480.
38. J.-D. Fourneron, A. Archelas, B. Vigne, R. Furstoss, Tetrahedron 1987, 43, 2273.
39. A. Archelas, R. Furstoss, D. Srairi, G. Maury, Bull. Soc. Chim. France 1986, 234.
40. (a) B. Vigne, A. Archelas, J. D. Fourneron, R. Furstoss, Tetrahedron 1986, 42, 2451.
41. (b) B. Vigne, A. Archelas, J.-D. Fourneron, R. Furstoss, Now. J. Chim. 1987, 11, 297.
42. (c) B. Vigne, A. Archelas, Furstoss, Tetrahedron 1991, 47, 1447.
43. (a) R. Furstoss, A. Archelas, J. D. Fourneron, B. Vigne, in Enzymes as Catalysts in Organic Synthesis; M. P. Schneider, Ed.; D. Reidel: 1986; pp 361.
44. (a) R. Furstoss, A. Archelas, J. D. Fourneron, B. Vigne, in Enzymes as Catalysts in Organic Synthesis; M. P. Schneider, Ed.; D. Reidel: 1986; pp 361.
45. J. D. Prail, S. M. Roberts, A. J. Willetts, J. Chem. Soc., Chem. Commun. 1990, 2854.
46. S. Pietz, R. Fröhlich, G. Haufe, preceding publication.
47. (a) M. J. S. Dewar, E. G. Zoebisch, Theochem 1988, 180, 1.
48. (b) M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. Stuart, J. Am. Chem. Soc. 1985, 107, 3902.
49. (c) MOPAC 6, AM1, Qcpe Program # 455.
50. (d) U. Höweler, MOBY Version 1.5, Springer-Verlag, Berlin, 1992.
51. (d) The calculations were performed in collaboration with C. Maerker (P. von R. Schleyer's group, Universität Erlangen-Nürnberg).
52. (a) J. T. Groves, G. A. Mc Clusky, J. Am. Chem. Soc. 1976, 98, 859.
53. (b) T. McMurry, J. T. Groves, in Cytochrome P-450: Structure, Mechanism and Biochemistry; P. R. Ortiz de Montellano, Ed., Plenum Press, New York, 1986, pp 1-28.
54. (c) F. P. Guengerich, T. L. Macdonald, FASEB J. 1990, 4, 2453.
55. (d) J. T. Groves, Y.-Z. Han, in Cytochrome P-450. Mechanism and Biochemistry, P. R. Ortiz de Montellano, 2nd ed., Plenum Press, New York, 1995.
56. (a) M. Newcomb, M.-L. Le Tadic-Biadatti, D. L. Chestney, E. S. Roberts, P. F. Hollenberg, J. Am. Chem. Soc. 1995, 117, 12085.
57. (b) M. Newcomb, M.-L. Le Tadic-Biadatti, D. A. Putt, P. F. J. Hollenberg, J. Am. Chem. Soc. 1995, 117, 3312.
58. (c) S.-Y. Choi, P. E. Eaton, P. F. Hollenberg, K. E. Liu, S. J. Lippard, M. Newcomb, D. A. Putt, S. P. Upadhyaya, Y. Xiong, J. Am. Chem. Soc. 1996, 118, 6547.
59. E. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Carbon Compounds, Wiley, New York, 1994
60. S. Pietz, G. Haufe, R. Fröhlich, M. Grehl, Acta Cryst. 1996, C52, 469.
61. (a) J. B. Hendrickson, J. Am. Chem. Soc. 1967, 89, 7036, 7043, 7047.
62. (b) F. A. L. Anet, Topics Curr. Chem. 1974, 45, 169.
63. (c) H. J. Schneider, T. Keller, R. Price, Org. Magn. Res., 1972, 4, 907.
64. E. Kleinpeter, G. Haufe, A. Wolf, K. Schulze, Tetrahedron, 1987, 43, 559.
65. G. Haufe, A. Wolf, K. Schulze, Tetrahedron 1986, 42, 4719.
66. J. K. Withesell, R. S. Matthews, P. A. Solomon, Tetrahedron Lett. 1976, 1549.
67. K. Biemann, G. Spiteller, J. Am. Chem. Soc. 1962, 84, 4578.