Enhancing the Enantioselectivity of an Epoxide Hydrolase by Directed Evolution

Organic Letters

Volumn 6, Issue 2, 2004, Pages 177-180

  Reetz, Manfred T ^a   Torre, Claudia ^a   Eipper, Andreas ^a   Lohmer, Renate ^a   Hermes, Marcus ^a   Brunner, Birgit ^a   Maichele, Andrea ^a   Bocola, Marco ^a   Arand, Michael ^b   Cronin, Annette ^b   Genzel, Yvonne ^c   Archelas, Alain ^c   Furstoss, Roland ^c  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^b UNIVERSITY OF WÜRZBURG   (Germany)

^c AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; DIPHENYL ETHER DERIVATIVE; EPOXIDE; EPOXIDE HYDROLASE; FUNGAL ENZYME; MUTANT PROTEIN;

AMINO ACID SUBSTITUTION; ARTICLE; ASPERGILLUS NIGER; ENANTIOSELECTIVITY; ENZYME ACTIVE SITE; ENZYME KINETICS; ERROR; HYDROLYSIS; MOLECULAR EVOLUTION; POLYMERASE CHAIN REACTION;

ASPERGILLUS NIGER; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; DIRECTED MOLECULAR EVOLUTION; EPOXIDE HYDROLASES; KINETICS; MOLECULAR STRUCTURE; PHENYL ETHERS; PROTEIN CONFORMATION; STEREOISOMERISM;

EID: 0842325300     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035898m     Document Type: Article

References (43)

1. Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421-431.
2. (a) Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer: Berlin, 1997.
3. (b) Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis: A Comprehensive Handbook, 2nd ed.; VCH: Weinheim, 2002; Vol. I-III.
4. (a) Archer, I. V. J. Tetrahedron 1997, 53, 15617-15662.
5. (b) Orru, R. V. A.; Faber, K. Curr. Opin. Chem. Biol. 1999, 3, 16-21.
6. (c) Steinreiber, A.; Mayer, S. F.; Faber, K. Synthesis 2001, 2035-2039.
7. (d) Archelas, A.; Furstoss, R. Curr. Opin. Chem. Biol. 2001, 5, 112-119.
8. (e) Archelas, A.; Furstoss, R. Trends Biotechnol. 1998, 16, 108-116.
9. (f) Bellucci, G.; Chiappe, C.; Cordoni, A.; Ingrosso, G. Tetrahedron Lett. 1996, 37, 9089-9092.
10. (g) Arand, M.; Müller, F.; Mecky, A.; Hinz, W.; Urban, P.; Pompon, D.; Kellner, R.; Oesch, F. Biochem. J. 1999, 337, 37-43.
11. (h) Arand, M.; Wagner, H.; Oesch, F. J. Biol. Chem. 1996, 271, 4223-4229.
12. Commercially available from Fluka/Aldrich/Sigma.
13. (a) Reetz, M. T.; Zonta, A.; Schimossek, K.; Liebeton, K.; Jaeger, K.-E. Angew. Chem., Int. Ed. Engl. 1997, 36, 2830-2832.
14. (b) Zha, D.; Wilensek, S.; Hermes, M.; Jaeger, K.-E.; Reetz, M. T. Chem. Commun. (Cambridge) 2001, 2664-2665.
15. (c) Reetz, M. T.; Wilensek, S.; Zha, D.; Jaeger, K.-E. Angew. Chem., Int. Ed. 2001, 40, 3589-3591.
16. (d) Reetz, M. T. Pure Appl. Chem. 2000, 72, 1615-1622.
17. (e) Reetz, M. T. Tetrahedron 2002, 58, 6595-6602.
18. (a) Arnold, F. H. Nature 2001, 409, 253-257.
19. (b) Powell, K. A.; Ramer, S. W.; del Cardayré, S. B.; Stemmer, W. P. C.; Tobin, M. B.; Longchamp, P. F.; Huisman, G. W. Angew. Chem., Int. Ed. 2001, 40, 3948-3959.
20. (c) Brakmann, S.; Johnsson, K. Directed Molecular Evolution of Proteins (or How to Improve Enzymes for Biocatalysis); Wiley-VCH: Weinheim, Germany, 2002.
21. (d) Arnold, F. H.; Georgiou, G. Directed Enzyme Evolution: Screening and Selection Methods; Humana Press: Totowa, NJ, 2003; Vol. 230.
22. Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284-310.
23. Bocola, M.; Otte, N.; Jaeger, K.-E.; Reetz, M. T.; Thiel, W. ChemBioChem, in press.
24. Torre, C. Dissertation, Ruhr-Universität Bochum, Bochum, Germany, 2003.
25. Genzel, Y.; Archelas, A.; Furstoss, R. Unpublished results.
26. Arand, M.; Hemmer, H.; Dürk, H.; Baratti, J.; Archelas, A.; Furstoss, R.; Oesch, F. Biochem. J. 1999, 344, 273-280.
27. Visser, J.; Archelas, A.; Arand, M.; Furstoss, R. Unpublished results.
28. Schrader, W.; Eipper, A.; Pugh, D. J.; Reetz, M. T. Can. J. Chem. 2002, 80, 626-632.
29. Zocher, F.; Enzelberger, M. M.; Bornscheuer, U. T.; Hauer, B.; Schmid, R. D. Anal. Chim. Acta 1999, 391, 345-351.
30. Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299.
31. (a) Zou, J. Y.; Hallberg, B. M.; Bergfors, T.; Oesch, F.; Arand, M.; Mowbray, S. L.; Jones, T. A. Structure (London) 2000, 8, 111-122.
32. (b) http://www.pdb.ccdc.cam.ac.uk/pdb.
33. (a) Zhao, H.; Arnold, F. H. Prot. Eng. 1999, 12, 47-53.
34. (b) Arnold, F. H.; Wintrode, P. L.; Miyazaki, K.; Gershenson, A. Trends Biochem. Sci. 2001, 26, 100-106.
35. (c) Iffland, A.; Tafelmeyer, P.; Saudan, C.; Johnsson, K. Biochem. 2000, 39, 10790-10798.
36. (d) Kumar, M.; Kannan, K. K.; Hosur, M. V.; Bhavesh, N. S.; Chatterjee, A.; Mittal, R.; Hosur, R. V. Biochem. Biophys. Res. Commun. 2002, 294, 395-401.
37. (e) Agarwal, P. K.; Billeter, S. R.; Rajagopalan, P. T. R.; Benkovic, S. J.; Hammes-Schiffer, S. Proc. Natl. Acad. Sci. 2002, 99, 2794-2799.
38. 5 (a) Fong, S.; Machajewski, T. D.; Mak, C. C.; Wong, C.-H. Chem. Biol. 2000, 7, 873-883. (b) May, O.; Nguyen, P. T.; Arnold, F. H. Nat. Biotechnol. 2000, 18, 317-320. (c) Henke, E.; Bornscheuer, U. T. Biol. Chem. 1999, 380, 1029-1033. (d) Horsman, G. P.; Liu, A. M. F.; Henke, E.; Bornscheuer, U. T.; Kazlauskas, R. J. Chem. Eur. J. 2003, 9, 1933-1939. (e) DeSantis, G.; Wong, K.; Farwell, B.; Chatman, K.; Zhu, Z.; Tomlinson, G.; Huang, H.; Tan, X.; Bibbs, L.; Chen, P.; Kretz, K.; Burk, M. J. J. Am. Chem. Soc. 2003, 125, 11476-11477.
39. 5 (a) Fong, S.; Machajewski, T. D.; Mak, C. C.; Wong, C.-H. Chem. Biol. 2000, 7, 873-883. (b) May, O.; Nguyen, P. T.; Arnold, F. H. Nat. Biotechnol. 2000, 18, 317-320. (c) Henke, E.; Bornscheuer, U. T. Biol. Chem. 1999, 380, 1029-1033. (d) Horsman, G. P.; Liu, A. M. F.; Henke, E.; Bornscheuer, U. T.; Kazlauskas, R. J. Chem. Eur. J. 2003, 9, 1933-1939. (e) DeSantis, G.; Wong, K.; Farwell, B.; Chatman, K.; Zhu, Z.; Tomlinson, G.; Huang, H.; Tan, X.; Bibbs, L.; Chen, P.; Kretz, K.; Burk, M. J. J. Am. Chem. Soc. 2003, 125, 11476-11477.
40. 5 (a) Fong, S.; Machajewski, T. D.; Mak, C. C.; Wong, C.-H. Chem. Biol. 2000, 7, 873-883. (b) May, O.; Nguyen, P. T.; Arnold, F. H. Nat. Biotechnol. 2000, 18, 317-320. (c) Henke, E.; Bornscheuer, U. T. Biol. Chem. 1999, 380, 1029-1033. (d) Horsman, G. P.; Liu, A. M. F.; Henke, E.; Bornscheuer, U. T.; Kazlauskas, R. J. Chem. Eur. J. 2003, 9, 1933-1939. (e) DeSantis, G.; Wong, K.; Farwell, B.; Chatman, K.; Zhu, Z.; Tomlinson, G.; Huang, H.; Tan, X.; Bibbs, L.; Chen, P.; Kretz, K.; Burk, M. J. J. Am. Chem. Soc. 2003, 125, 11476-11477.
41. 5 (a) Fong, S.; Machajewski, T. D.; Mak, C. C.; Wong, C.-H. Chem. Biol. 2000, 7, 873-883. (b) May, O.; Nguyen, P. T.; Arnold, F. H. Nat. Biotechnol. 2000, 18, 317-320. (c) Henke, E.; Bornscheuer, U. T. Biol. Chem. 1999, 380, 1029-1033. (d) Horsman, G. P.; Liu, A. M. F.; Henke, E.; Bornscheuer, U. T.; Kazlauskas, R. J. Chem. Eur. J. 2003, 9, 1933-1939. (e) DeSantis, G.; Wong, K.; Farwell, B.; Chatman, K.; Zhu, Z.; Tomlinson, G.; Huang, H.; Tan, X.; Bibbs, L.; Chen, P.; Kretz, K.; Burk, M. J. J. Am. Chem. Soc. 2003, 125, 11476-11477.
42. 5 (a) Fong, S.; Machajewski, T. D.; Mak, C. C.; Wong, C.-H. Chem. Biol. 2000, 7, 873-883. (b) May, O.; Nguyen, P. T.; Arnold, F. H. Nat. Biotechnol. 2000, 18, 317-320. (c) Henke, E.; Bornscheuer, U. T. Biol. Chem. 1999, 380, 1029-1033. (d) Horsman, G. P.; Liu, A. M. F.; Henke, E.; Bornscheuer, U. T.; Kazlauskas, R. J. Chem. Eur. J. 2003, 9, 1933-1939. (e) DeSantis, G.; Wong, K.; Farwell, B.; Chatman, K.; Zhu, Z.; Tomlinson, G.; Huang, H.; Tan, X.; Bibbs, L.; Chen, P.; Kretz, K.; Burk, M. J. J. Am. Chem. Soc. 2003, 125, 11476-11477.
43. Cedrone, F.; Niel, S.; Roca, S.; Bhatnagar, T.; Ait-Abdelkader, N.; Torre, C.; Krumm, H.; Maichele, A.; Reetz, M. T.; Baratti, J. C. Biocatal. Biotransform. Submitted.