Directed Evolution of Enantioconvergency: The Case of an Epoxide Hydrolase-Catalyzed Reaction of a Racemic Epoxide

ChemCatChem

Volumn 2, Issue 8, 2010, Pages 958-961

  Zheng, Huabao ^a   Kahakeaw, Daniel ^a   Acevedo, Juan Pablo ^a   Reetz, Manfred T ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Alcohols; Directed evolution; Enantioselectivity; Enzymes; Hydrolases

Indexed keywords

EID: 78149264575     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201000122     Document Type: Article

References (66)

1. Recent reviews of directed evolution.
2. T. W. Johannes, H. Zhao, Curr. Opin. Microbiol. 2006, 9, 261-267;
3. S. Lutz, U. T. Bornscheuer, Protein Engineering Handbook, Vol. 1-2, Wiley-VCH, Weinheim, 2009;
4. N. J. Turner, Nat. Chem. Biol. 2009, 5, 567-573;
5. C. Jäckel, P. Kast, D. Hilvert, Annu. Rev. Biophys. Biomol. Struct. 2008, 37, 153-173;
6. S. Bershtein, D. S. Tawfik, Curr. Opin. Chem. Biol. 2008, 12, 151-158;
7. P. A. Romero, F. H. Arnold, Nat. Rev. Mol. Cell Biol. 2009, 10, 866-876;
8. L. G. Otten, F. Hollmann, I. W. C. E. Arends, Trends Biotechnol. 2010, 28, 46-54;
9. A. V. Shivange, J. Marienhagen, H. Mundhada, A. Schenk, U. Schwaneberg, Curr. Opin. Chem. Biol. 2009, 13, 19-25;
10. M. T. Reetz in Asymmetric Organic Synthesis with Enzymes (Eds.: V. Gotor, I. Alfonso, E. García- Urdiales), Wiley-VCH, Weinheim, 2008, pp. 21-63.
11. M. T. Reetz, A. Zonta, K. Schimossek, K. Liebeton, K.-E. Jaeger, Angew. Chem. 1997, 109, 2961-2963
12. M. T. Reetz, A. Zonta, K. Schimossek, K. Liebeton, K.-E. Jaeger, Angew. Chem. Int. Ed. Engl. 1997, 36, 2830-2832.
13. Reviews of directed evolution of stereoselectivity.
14. M. T. Reetz, Proc. Natl. Acad. Sci. USA 2004, 101, 5716-5722;
15. M. T. Reetz in Advances in Catalysis, Vol. 49 (Eds.: B. C. Gates, H. Knözinger), Elsevier, San Diego, 2006, pp. 1-69;
16. M. T. Reetz, J. Org. Chem. 2009, 74, 5767-5778.
17. Reviews of epoxide hydrolases.
18. A. Archelas, R. Furstoss, Curr. Opin. Chem. Biol. 2001, 5, 112-119;
19. K. Faber, R. V. A. Orru in Enzyme Catalysis in Organic Synthesis (Eds.: K. Drauz, H. Waldmann), Wiley-VCH, Weinheim, 2002, pp. 579-608;
20. E. J. de Vries, D. B. Janssen, Curr. Opin. Biotechnol. 2003, 14, 414-420;
21. M. S. Smit, M. Labuschagné, Curr. Org. Chem. 2006, 10, 1145-1161;
22. E. Y. Lee, Biotechnol. Lett. 2008, 30, 1509-1514;
23. W. J. Choi, Appl. Microbiol. Biotechnol. 2009, 84, 239-247;
24. C. Morisseau, B. D. Hammock, Annu. Rev. Pharmacol. Toxicol. 2005, 45, 311-333.
25. [9]
26. B. van Loo, J. H. L. Spelberg, J. Kingma, T. Sonke, M. G. Wubbolts, D. B. Janssen, Chem. Biol. 2004, 11, 981-990;
27. E. Y. Lee, M. L. Shuler, Biotechnol. Bioeng. 2007, 98, 318-327;
28. L. Rui, L. Cao, W. Chen, K. F. Reardon, T. K. Wood, Appl. Environ. Microbiol. 2005, 71, 3995-4003;
29. M. Kotik, V. Stepanek, P. Kyslik, H. Maresova, J. Biotechnol. 2007, 132, 8-15.
30. E. N. Jacobsen, Acc. Chem. Res. 2000, 33, 421-431.
31. An exception is epichlorohydrin which undergoes base-catalyzed rearrangement with concomitant racemization.
32. Examples of enantioconvergent epoxide hydrolase-catalyzed reactions of chiral epoxides.
33. S. Pedragosa-Moreau, C. Morisseau, J. Zylber, A. Archelas, J. Baratti, R. Furstoss, J. Org. Chem. 1996, 61, 7402-7407;
34. G. Bellucci, C. Chiappe, A. Cordoni, Tetrahedron: Asymmetry 1996, 7, 197-202;
35. W. Kroutil, M. Mischitz, K. Faber, J. Chem. Soc. Perkin Trans. 1 1997, 3629-3636;
36. S. F. Mayer, A. Steinreiber, R. V. A. Orru, K. Faber, Eur. J. Org. Chem. 2001, 4537-4542;
37. S. Karboune, A. Archelas, R. Furstoss, J. C. Baratti, Biocatal. Biotransform. 2005, 23, 397-405;
38. L. Cao, J. Lee, W. Chen, T. K. Wood, Biotechnol. Bioeng. 2006, 94, 522-529;
39. W. Xu, J.-H. Xu, J. Pan, Q. Gu, X.-Y. Wu, Org. Lett. 2006, 8, 1737-1740;
40. S. Hwang, C. Y. Choi, E. Y. Lee, Biotechnol. Lett. 2008, 30, 1219-1225;
41. S. Lin, G. P. Horsman, Y. Chen, W. Li, B. Shen, J. Am. Chem. Soc. 2009, 131, 16410-16417.
42. M. T. Reetz, C. Torre, A. Eipper, R. Lohmer, M. Hermes, B. Brunner, A. Maichele, M. Bocola, M. Arand, A. Cronin, Y. Genzel, A. Archelas, R. Furstoss, Org. Lett. 2004, 6, 177-180;
43. M. T. Reetz, L.-W. Wang, M. Bocola, Angew. Chem. 2006, 118, 1258-1263
44. M. T. Reetz, L.-W. Wang, M. Bocola, Angew. Chem. Int. Ed. 2006, 45, 1236-1241
45. Erratum: M. T. Reetz, L.-W. Wang, M. Bocola, Angew. Chem. 2006, 118, 2556
46. M. T. Reetz, D. Kahakeaw, R. Lohmer, Chem Bio Chem 2008, 9, 1797-1804.
47. M. T. Reetz, M. Bocola, J. D. Carballeira, D. Zha, A. Vogel, Angew. Chem. 2005, 117, 4264-4268
48. M. T. Reetz, M. Bocola, J. D. Carballeira, D. Zha, A. Vogel, Angew. Chem. Int. Ed. 2005, 44, 4192-4196;
49. D. J. Bougioukou, S. Kille, A. Taglieber, M. T. Reetz, Adv. Synth. Catal. 2009, 351, 3287-3305;
50. M. T. Reetz, J. D. Carballeira, Nat. Protoc. 2007, 2, 891-903;
51. M. T. Reetz, D. Kahakeaw, J. Sanchis, Mol. Bio Syst. 2009, 5, 115-122.
52. J. Y. Zou, B. M. Hallberg, T. Bergfors, F. Oesch, M. Arand, S. L. Mowbray, T. A. Jones, Structure 2000, 8, 111-122;
53. http://www.pdb.ccdc.cam.ac.uk/pdb.
54. L. Rui, Y. M. Kwon, A. Fishman, K. F. Reardon, T. K. Wood, Appl. Environ. Microbiol. 2004, 70, 3246-3252;
55. W. M. Patrick, A. E. Firth, Biomol. Eng. 2005, 22, 105-112;
56. A. D. Bosley, M. Ostermeier, Biomol. Eng. 2005, 22, 57-61;
57. M. Denault, J. N. Pelletier in Protein Engineering Protocols, Vol. 352 (Eds.: K. M. Arndt, K. M. Müller), Humana Press, Totowa, NJ, 2007, pp. 127-154.
58. D. Kahakeaw, M. T. Reetz, Chem. Asian J. 2008, 3, 233-238.
59. D. Wahler, J.-L. Reymond, Angew. Chem. 2002, 114, 1277-1280
60. D. Wahler, J.-L. Reymond, Angew. Chem. Int. Ed. 2002, 41, 1229-1232;
61. J.-L. Reymond, Enzyme Assays-High-throughput Screening, Genetic Selection and Fingerprinting, Wiley-VCH, Weinheim, 2006.
62. M. T. Reetz, M. Bocola, L.-W. Wang, J. Sanchis, A. Cronin, M. Arand, J. Zou, A. Archelas, A.-L. Bottalla, A. Naworyta, S. L. Mowbray, J. Am. Chem. Soc. 2009, 131, 7334-7343.
63. K. J. Bowers, E. Chow, H. Xu, R. O. Dror, M. P. Eastwood, B. A. Gregersen, J. L. Klepeis, I. Kolossváry, M. A. Moraes, F. D. Sacerdoti, J. K. Salmon, Y. Shan, D. E. Shaw, Proceedings of the ACM/IEEE Conference on Supercomputing (SC06), Tampa, Florida, 2006.
64. For a review of the theory of near-attack conformers in enzyme-catalyzed reactions, see.
65. T. C. Bruice, Acc. Chem. Res. 2002, 35, 139-148; for an MD study of epoxide hydrolases, see.
66. B. Schiøtt, T. C. Bruice, J. Am. Chem. Soc. 2002, 124, 14558-14570.