Deracemization of (±)-2,3-disubstituted oxiranes via biocatalytic hydrolysis using bacterial epoxide hydrolases: Kinetics of an enantioconvergent process

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 24, 1997, Pages 3629-3636

  Kroutil, Wolfgang ^a   Mischitz, Martin ^a   Faber, Kurt ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748638617     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a704812b     Document Type: Article

References (35)

1. H. C. Kolb, M. S. VanNieuwenhze and K. B. Sharpless, Chem. Rev., 1994, 94, 2483.
2. V. Schurig and F. Betschinger, Chem. Rev., 1992, 92, 873.
3. R. A. Johnson and K. B. Sharpless, in Catalytic Asymmetric Synthesis, ed. I. Ojima, Verlag Chemie, New York, 1993, p. 103;
4. E. N. Jacobsen, W. Zhang, A. R. Muci, J. R. Ecker and L. Deng, J. Am. Chem. Soc., 1991, 113, 7063;
5. K. Konishi, K. Oda, K. Nishida, T. Aida and S. Inoue, J. Am. Chem. Soc., 1992, 114, 1313.
6. J. A. M. de Bont, Tetrahedron: Asymmetry, 1993, 4, 1331;
7. D. J. Leak, P. J. Aikens and M. Seyed-Mahmoudian, Trends Biotechnol., 1992, 10, 256;
8. A. N. Onumonu, A. Colocoussi, C. Matthews, M. P. Woodland and D. J. Leak, Biocatalysis, 1994, 10, 211;
9. P. Besse and H. Veschambre, Tetrahedron, 1994, 50, 8885;
10. S. Pedragosa-Moreau, A. Archelas and R. Furstoss, Bull. Soc. Chim. Fr., 1995, 132, 769.
11. F. Oesch, Xenobiotica, 1972, 3, 305.
12. S. Pedragosa-Moreau, A. Archelas and R. Furstoss, Tetrahedron, 1996, 52, 4593.
13. S. Pedragosa-Moreau, A. Archelas and R. Furstoss, J. Org. Chem., 1993, 58, 5533.
14. (a) M. Mischitz, W. Kroutil, U. Wandel and K. Faber, Tetrahedron: Asymmetry, 1995, 6, 1261;
15. (b) I. Osprian, W. Kroutil, M. Mischitz and K. Faber, Tetrahedron: Asymmetry, 1997, 8, 65.
16. (a) For a review see: K. Faber. M. Mischitz and W. Kroutil, Acta Chem. Scand., 1996, 50, 249;
17. (b) For the isolation and characterization of a highly selective bacterial epoxide hydrolase see: M. Mischitz, K. Faber and A. Willetts, Biotechnol. Lett., 1995, 17, 893.
18. M. Mischitz, C. Mirtl, R. Saf and K. Faber, Tetrahedron: Asymmetry, 1996, 7, 2041.
19. C.-S. Chen, Y. Fujimoto, G. Girdaukas and C. J. Sih, J. Am. Chem. Soc., 1982, 104, 7294.
20. For a preliminary communication see: W. Kroutil, M. Mischitz, P. Plachota and K. Faber, Tetrahedron Lett., 1996, 37, 8379.
21. W. Kroutil, I. Osprian, M. Mischitz and K. Faber, Synthesis, 1997, 156.
22. G. M. Lacourciere and R. N. Armstrong, J. Am. Chem. Soc., 1993, 115, 10466;
23. B. D. Hammock, F. Pinot, J. K. Beetham, D. F. Grant, M. E. Arand and F. Oesch, Biochem. Biophys. Res. Commun., 1994, 198, 850;
24. M. Arand, H. Wagner and F. Oesch, J. Biol. Chem., 1996, 271, 4223.
25. 4-dihydroxylation of the corresponding Z- and E-alkene.
26. 18O-labelling experiments) is indicated by subscript arabic numerals.
27. 1 during the whole course of the reaction. See: S. El-Baba, J.-C. Poulin and H. B. Kagan, Tetrahedron, 1984, 40, 4275.
28. The absence of spontaneous hydrolysis under the reaction conditions employed was verified using blank-experiments in the absence of biocatalyst. No trace of hydrolysis was observed within ∼600 h.
29. MS).
30. 0.
31. 2).
32. G. Bellucci, G. Berti, G. Catelani and E. Mastrorilli, J. Org. Chem., 1981, 46, 5148.
33. G. Bellucci, C. Chiappe and A. Cordoni, Tetrahedron: Asymmetry, 1996, 7, 197.
34. E. Blée and F. Schuber, Eur. J. Biochem., 1995, 230, 229.
35. Obtained via transesterification of commercially available tert-butyl (R)-2-hydroxybutanoate using catalytic NaOEt in ethanol (room temp.; 24 h).