Biocatalysis in ionic liquids: The stereoconvergent hydrolysis of trans-β-methylstyrene oxide catalyzed by soluble epoxide hydrolase

Journal of Molecular Catalysis B: Enzymatic

Volumn 27, Issue 4-6, 2004, Pages 243-248

  Chiappe, Cinzia ^a   Leandri, Elsa ^a   Lucchesi, Serena ^a   Pieraccini, Daniela ^a   Hammock, Bruce D ^b   Morisseau, Christophe ^b  

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Biocatalysis; Ionic liquids; Stereoconvergent hydrolysis

Indexed keywords

CATALYSIS; ENZYMES; HYDROLYSIS;

BIOCATALYSIS; IONIC LIQUIDS;

BIOCATALYSTS;

ALCOHOL DERIVATIVE; BETA METHYLSTYRENE OXIDE; BORIC ACID; BUFFER; EPOXIDE HYDROLASE; FLUOROPHOSPHATE; IMIDAZOLE DERIVATIVE; PROPANE; STYRENE DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOCATALYST; CATALYSIS; HYDROLYSIS; LIQUID; SOLUBILITY;

EID: 1242293116     PISSN: 13811177     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcatb.2003.12.008     Document Type: Article

References (47)

1. A.M.P. Koshinen, A.M. Klibanov, Enzymatic Reactions in Organic Media, Blackie Academic & Professional, Glasgow, 1996.
2. K. Faber, Biotransformtion in Organic Chemistry, 3rd ed., Springer, Berlin, Germany, 1997.
3. Klibanov A.M. Trends Biotechnol. 15:1997;97.
4. Kragl U., Eckstein M., Kraftzik N. Chem. Biotechnol. 13:2002;565.
5. van Rantwijk F., Lau R.M., Sheldon R.A. Trends Biotechnol. 21:2003;131.
6. Park S., Kazlauskas R.J. Curr. Opin. Biotechnol. 14:2003;1.
7. Holbrey J.D., Seddon K.R. Clean Prod. Process. 1:1999;223.
8. Earle M.J., Seddon K.R. Pure Appl. Chem. 72:2000;1391.
9. Welton T. Chem. Rev. 99:1999;2071.
10. Wasserscheid P., Keim W. Angew. Chem. Int. Ed. 39:2000;3773.
11. R.A. Sheldon, Chem. Commun. (2001) 2399.
12. Olivier-Bourbigou H., Magna L. J. Mol. Catal. A. 182:2002;419.
13. Dupont J., de Souza R.F., Suarez P.A.Z. Chem. Rev. 102:2002;3667.
14. Lau R.M., van Rantwijk F., Seddon K.R., Sheldon R.A. Org. Lett. 2:2000;4189.
15. Park S., Kazlauskas R.J. J. Org. Chem. 66:2001;8395.
16. S.H. Schöfer, N. Kaftzik, P. Wassersheid, U. Kragl, Chem. Commun. (2001) 425.
17. Kim K.W., Song B., Kim M.J. Org. Lett. 3:2001;1507.
18. Nara S.J., Harjani J.R., Salunkhe M.M. Tetrahedron Lett. 43:2002;2979.
19. Lozano P., de Diego T., Carrié D., Vaultier M., Iborra J.L. J. Mol. Catal. B. 21:2003;9.
20. Kafzik N., Wassersheid P., Kragl U. Org. Process. Res. Dev. 6:2002;553.
21. Howarth J., James P., Dai J. Tetrahedron Lett. 42:2001;7517.
22. Savle P.S., Lamoereaux M.J., Berry J.F., Gandour R.D. Tetrahedron Asym. 9:1998;1843.
23. Steinraber A., Faber K. Curr. Opin. Biotechnol. 12:2001;552.
24. Archelas A., Furstoss R. Curr. Opin. Chem. Biol. 5:2001;112.
25. Archer I.V.J. Tetrahedron. 53:1997;15617.
26. Chiappe C., Cordoni G., Lo Moro G., Palese C.D. Tetrahedron Asym. 9:1998;341.
27. Williamson K.C., Morisseau C.M., Maxwell J.E., Hammock B.D. Tetrahedron Asym. 11:2000;4451.
28. Kroutil W., Mischitz M., Faber K. J. Chem. Soc., Perkin. 1:1997;3629.
29. Moussou P., Archelas A., Baratti R., Furstoss R. J. Org. Chem. 63:1998;3532.
30. Weijers C.A.G.M., Botes A.L., van Dick M.S., de Bont M. Tetrahedron Asym. 9:1998;467.
31. Morisseau C., Beetham J.K., Pinot F., Debernard S., Mewman J.W., Hammock B.D. Arch. Biochem. Biophys. 387:2000;321.
32. Stapleton A., Beetham J.K., Pinot F., Garbarino J.E., Rockhold D.R., Friedman M., Hammock B.D., Belknap W.R. Plant J. 6:1994;251.
33. L. Zhao, E. Mathur, D. Weiner, T. Richardson, A. Milaln, M. Burk, B. Han, PCT Int. Appl. (2003) 400.
34. Choi W.J., Lee E.Y., Yoon S.J., Yang S.-T., Choi C.Y. J. Biosci. Bioeng. 88:1999;339.
35. Bellucci G., Chiappe C., Cordoni A. Tetrahedron Asym. 7:1996;197.
36. R.T. Fuller, H.C. Carlin, D. de Long, J. Haworth, J. Chem. Soc., Chem. Commun. (1994) 299.
37. L. Cammarata, S.G. Kazarian, P.A. Salter, T. Welton, Phys. Chem. Chem. Phys. (2001) 5192.
38. Chiappe C., Pieraccini D., Saullo P. J. Org. Chem. 68:2003;6710.
39. Billard I., Moutiers G., El Azzi A., Gaillard C., Mariet C., Lützenkinchen J. Inorg. Chem. 42:2003;1726.
40. Grant D.F., Stroms D.H., Hammock B.D. J. Biol. Chem. 3268:1993;17628.
41. Morisseau C., Beetham J.K., Pinot F., Debernard S., Newman J.W., Hammock B.D. Arch. Biochem. Biophys. 378:2000;321.
42. In this work we used both commercial (Solvent Innovation GmbH) and synthesized ILs but always particular attention was paid to the purity.
43. Huddleston J.G., Visser A.E., Reichert W.M., Willauer H.D., Broker G.A., Rogers R.D., Green R.D. Green Chem. 3:2001;156.
44. Dzyuba S.V., Bartsch R.A. Chem. Phys. Chem. 3:2002;161.
45. Halling P. J. Enzyme Microb. Technol. 16:1994;178.
46. For a discussion on the effect of the IL structure on the rate constants for diffusion in these solvents see: A.J. McLean, M.J. Muldoon, C.M. Gordon, I.R. Dunkin, Chem. Commun. (2002) 1880.
47. Jastorff B., Störmann R., Ranke J., Mölter K., Stock F., Oberheitmann B., Hoffmann W., Hoffmann J., Nüchter M., Ondruschka B., Filser J. Green Chem. 5:2003;136.