Directed evolution of an enantioselective enoate-reductase: Testing the utility of iterative saturation mutagenesis

Advanced Synthesis and Catalysis

Volumn 351, Issue 18, 2009, Pages 3287-3305

  Bougioukou, J Despina ^a   Kille, Sabrina ^a   Taglieber, Andreas ^a   Reetz, Manfredt ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Asymmetric reduction; Directed evolution; Enantioselectivity; Enoate reductase; Screening assay

Indexed keywords

EID: 73349113954     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900644     Document Type: Article

References (100)

1. Recent reviews of directed evolution of enantioselective enzymes: a) M. T. Reetz, in: Asymmetric Organic Synthesis with Enzymes, (Eds.: V. Gotor, I. Alfonso, E. García-Urdiales), Wiley-VCH, Weinheim, 2008, pp 21-63;
2. M. T. Reetz, J. Org. Chem. 2009, 74, 5767-5778.
3. K. Drauz, H. Waldmann, Enzyme Catalysis in Organic Synthesis: A Comprehensive Handbook, Vols. I-III, 2nd edn., Wiley-VCH, Weinheim, 2002;
4. A. Liese, K. Seelbach, C. Wandrey, Industrial Biotransformations, 2nd edn., Wiley-VCH, Weinheim, 2006.
5. P. J. Walsh, M. C. Kozlowski, Fundamentals of Asymmetric Catalysis, University Science Books, Sausalito, CA, 2009;
6. H.-U. Blaser, E. Schmidt, Asymmetric Catalysis on Industrial Scales, Wiley-VCH, Weinheim, 2004.
7. E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis, Vols. I-III, Springer, Berlin, 1999.
8. G. Lelais, D. W C. MacMillan, Aldrichimica Acta 2006, 39, 79-87;
9. J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719-724;
10. A. Berkessel, H. Gröger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2004.
11. M. T. Reetz, A. Zonta, K. Schimossek, K. Liebeton, K.-E. Jaeger, Angew. Chem. 1997, 109, 2961-2963;
12. Angew. Chem. Int. Ed. Engl. 1997, 36, 2830-2832;
13. M. T. Reetz, Pure Appl. Chem. 2000, 72, 1615-1622;
14. M. T. Reetz, Proc. Natl. Acad. Sci. USA 2004, 101, 5716-5722.
15. [1] a) S. Lutz, U. T. Bornscheuer, Protein Engineering Protocols, Vols. I and II, Wiley-VCH, Weinheim, 2009;
16. K. M. Arndt, K. M. Müller, Protein Engineering Protocols (Methods in Molecular Biology), Vol. 352, Humana Press, Totowa, NJ, 2007;
17. N. J. Turner, Nat. Chem. Biol. 2009, 5, 567-573;
18. C. Jäckel, P. Kast, D. Hilvert, Annu. Rev. Biophys. Biomol. Struct. 2008, 37, 153-173;
19. S. Bershtein, D. S. Tawfik, Curr. Opin. Chem. Biol. 2008, 12, 151-158;
20. P. A. Romero, F. H. Arnold, Nat. Rev. Mol. Cell Biol. 2009, 10, 866-876.
21. See, for example: a) S. Lutz, W M. Patrick, Curr. Opin. Biotechnol. 2004, 15, 291-297;
22. R. J. Fox, G. W Huisman, Trends Biotechnol. 2008, 26, 132-138;
23. A. Herman, D. S. Tawfik, Protein Eng. Des. Sel. 2007, 20, 219-226;
24. J. D. Bloom, M. M. Meyer, P. Meinhold, C. R. Otey, D. MacMillan, F. H. Arnold, Curr. Opin. Struct. Biol. 2005, 15, 447-452;
25. T S. Wong, D. Roccatano, M. Zacharias, U. Schwaneberg, J. Mol. Biol. 2006, 355, 858-871.
26. M. T Reetz, in: Evolutionary Methods in Biotechnology, (Eds.: S. Brakmann, A. Schwienhorst), Wiley-VCH, Weinheim, 2004, pp 113-141;
27. J.-L. Reymond, Enzyme Assays - High-throughput Screening, Genetic Selection and Fingerprinting, Wiley-VCH, Weinheim, 2006.
28. M. T Reetz, D. Kahakeaw, R. Lohmer, ChemBioChem 2008, 9, 1797-1804.
29. M. T Reetz, L.-W Wang, in part M. Bocola, Angew. Chem. 2006, 118, 1258-1263;
30. Erratum 2556; Angew. Chem. Int. Ed. 2006, 45, 1236-1241;
31. Erratum 2494.
32. M. T. Reetz, D. Kahakeaw, J. Sanchis, Mol. BioSyst. 2009, 5, 115-122;
33. M. T. Reetz, in: Protein Engineering Handbook, Vol. 2 (Eds.: S. Lutz, U. T. Bornscheuer), Wiley-VCH, Weinheim, 2009, pp 409-439.
34. M. T. Reetz, J. D. Carballeira, A. Vogel, Angew. Chem. 2006, 118, 7909-7915;
35. Angew. Chem. Int. Ed. 2006, 45, 7745-7751;
36. M. T. Reetz, J. D. Carballeira, Nat. Protoc. 2007, 2, 891-903.
37. M. T. Reetz, M. Bocola, J. D. Carballeira, D. Zha, A. Vogel, Angew. Chem. 2005, 117, 4264-4268;
38. Angew. Chem. Int. Ed. 2005, 44, 4192-4196;
39. C. M. Clouthier, M. M. Kayser, M. T. Reetz, J. Org. Chem. 2006, 71, 8431-8437;
40. J. D. Carballeira, P. Krumlinde, M. Bocola, A. Vogel, M. T. Reetz, J.-E. Bäckvall, Chem. Commun. 2007, 1913-1915.
41. S. Bartsch, R. Kourist, U. T. Bornscheuer, Angew. Chem. 2008, 120, 1531-1534;
42. Angew. Chem. Int. Ed. 2008, 47, 1508-1511;
43. L. Liang, J. Zhang, Z. Lin, Microb. Cell Fact. 2007, 6, 36;
44. R. Hawwa; S. D. Larsen, K. Ratia, A. D. Mesecar, J. Mol. Biol. 2009, 393, 36-57;
45. M. R. M. De Groeve, M. De Baere, L. Hoflack, T. Desmet, E. J. Vandamme, W. Soetaert, Protein Eng. Des. Sel. 2009, 22, 393-399;
46. K. Okrasa, C. Levy, M. Wilding, M. Goodhall, N. Baudendistel, B. Hauer, D. Leys, J. Micklefield, Angew. Chem. 2009, 121, 7827-7830;
47. Angew. Chem. Int. Ed. 2009, 48, 7691-7694;
48. A. G. Sandström, K. Engström, J. Nyhlen, A. Kasrayan, J.-E. Bäckvall, Protein Eng. Des. Sel. 2009, 22, 413-420.
49. T. B. Fitzpatrick, N. Amrhein, P. Macheroux, J. Biol. Chem. 2003, 278, 19891-19897.
50. O. Warburg, W Christian, Biochem. Z. 1933, 266, 377-411;
51. Y. S. Niino, S. Chakraborty, B. J. Brown, V. Massey, J. Biol. Chem. 1995, 270, 1983-1991.
52. R. E. Williams, N. C. Bruce, Microbiology 2002, 148, 1607-1614;
53. R. Stuermer, B. Hauer, M. Hall, K. Faber, Curr. Opin. Chem. Biol. 2007, 11, 203-213;
54. J. F. Chaparro-Riggers, T. A. Rogers, E. Vazquez-Figueroa, K. M. Polizzi, A. S. Bommarius, Adv. Synth. Catal. 2007, 349, 1521-1531;
55. M. Hall, C. Stueckler, W Kroutil, P. Macheroux, K. Faber, Angew. Chem. 2007, 119, 4008-4011;
56. Angew. Chem. Int. Ed. 2007, 46, 3934-3937;
57. A. Muller, B. Hauer, B. Rosche, Biotechnol. Bioeng. 2007, 98, 22-29;
58. A. Müller, R. Sturmer, B. Hauer, B. Rosche, Angew. Chem. 2007, 119, 3380-3382;
59. Angew. Chem. Int. Ed. 2007, 46, 3316-3318;
60. A. Fryszkowska, K. Fisher; J. M. Gardiner, G. M. Stephens, J. Org. Chem. 2008, 73, 4295-4298;
61. M. Hall, C. Stueckler, H. Ehammer, E. Pointner, G. Oberdorfer, K. Gruber, B. Hauer, R. Stuermer, W Kroutil, P. Macheroux, K. Faber, Adv. Synth. Catal. 2008, 350, 411-418;
62. B. Kosjek, F. J. Fleitz, P. G. Dormer; J. T. Kuethe; P. N. Devine, Tetrahedron: Asymmetry 2008, 19, 1403-1406;
63. H. S. Toogood, A. Fryszkowska, V. Hare; K. Fisher, A. Roujeinikova, D. Leys, J. M. Gardiner, G. M. Stephens, N. S. Scrutton, Adv. Synth. Catal. 2008, 350, 2789-2803.
64. S.-M. Lu, C. Bolm, Chem. Eur. J. 2008, 14, 7513-7516;
65. T. Ohshima, H. Tadaoka, K. Hori, N. Sayo, K. Mashima, Chem. Eur. J. 2008, 14, 2060-2066;
66. S.-M. Lu, C. Bolm, Angew. Chem. 2008, 120, 9052-9055;
67. Angew. Chem. Int. Ed. 2008, 47, 8920-8923;
68. C. J. Scheuermann née Taylor, C. Jaekel, Adv. Synth. Catal. 2008, 350, 2708-2714;
69. J. G. de Vries, C. J. Elsevier, Handbook of Homogeneous Hydrogenation, Vols. I-III, Wiley-VCH, Weinheim, 2006.
70. J. B. Tuttle, S. G. Ouellet, D. W C. MacMillan, J. Am. Chem. Soc. 2006, 128, 12662-12663;
71. N. J. A. Martin, B. List, J. Am. Chem. Soc. 2006, 128, 13368-13369.
72. K. Kitzing, T B. Fitzpatrick, C. Wilken, J. Sawa, G. P. Bourenkov, P. Macheroux, T Clausen, J. Biol. Chem. 2005, 280, 27904-27913.
73. S. K. Padhi, D. J. Bougioukou, J. D. Stewart, J. Am. Chem. Soc. 2009, 131, 3271-3280.
74. B. J. Brown, Z. Deng, P. A. Karplus, V. Massey, J. Biol. Chem. 1998, 273, 32753-32762;
75. R. M. Kohli, V. Massey, J. Biol. Chem. 1998, 273, 32763-32770;
76. D. Xu, R. M. Kohli, V. Massey, Proc. Natl. Acad. Sci. USA 1999, 96, 3556-3561.
77. Figure were created by using PyMOL: W L. DeLano, The PyMOL Molecular Graphics System, 2008, DeLano Scientific LLC, Palo, CA, USA http://www pymol.org.
78. L. Rui, Y. M. Kwon, A. Fishman, K. F. Reardon, T K. Wood, Appl. Environ. Microbiol. 2004, 70, 3246-3252;
79. A. D. Bosley, M. Ostermeier, Biomol. Eng. 2005, 22, 57-61;
80. M. A. Mena, P. S. Daugherty, Protein Eng. Des. Sel. 2005, 18, 559-561;
81. 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.
82. H. H. Hogrefe, J. Cline, G. L. Youngblood, R. M. Allen, BioTechniques 2002, 33, 1158-1165.
83. N refers to an equal mixture of nucleotides A, T, G, and C; D refers to an equal mixture of A, T and G; K refers to an equal mixture of G and T
84. J. Sanchis, L. Fernández, J. D. Carballeira, J. Drone, Y. Gumulya, H. Höbenreich, D. Kahakeaw, S. Kille, R. Lohmer, J. J.-P. Peyralans, J. Podtetenieff, S. Prasad, P. Soni, A. Taglieber, S. Wu, F. E. Zilly, M. T Reetz, Appl. Microbiol. Biotechnol. 2008, 81, 387-397.
85. M. Z. Li, S. J. Elledge, Nat. Methods 2007, 4, 251-256.
86. A. Airaksinen, T Hovi, Nucleic Acids Res. 1998, 26, 576-581.
87. K. M. Polizzi, M. Parikh, C. U. Spencer, I. Matsumura, J. H. Lee, M. J. Realff, A. S. Bommarius, Biotechnol. Prog. 2006, 22, 961-967;
88. K M. Polizzi, C. U. Spencer A. Dubey, I. Matsumura, J. H. Lee, M. J. Realff, A. S. Bommarius, J. Biomol. Screening 2005, 10, 856-864.
89. M. R. Martzen, S. M. McCraith, S. L. Spinelli, F. M. Torres, S. Fields, E. J. Grayhack, E. M. Phizicky, Science 1999, 286, 1153-1155.
90. K. Shimoda, N. Kubota; H. Hamada, Tetrahedron: Asymmetry 2004, 15, 2443-2446;
91. M. A. Swiderska; J. D. Stewart, J. Mol. Catal. B: Enzym. 2006, 42, 52-54.
92. T B. Fitzpatrick, S. Auweter, K. Kitzing; T Clausen, N. Amrhein, P. Macheroux, Protein Expression Purif. 2004, 36, 280-291.
93. A. S. Abramovitz; V. Massey, J. Biol. Chem. 1976, 251, 5321-5326.
94. S. Luetz, L. Giver, J. Lalonde, Biotechnol. Bioeng. 2008, 101, 647-653;
95. R. J. Fox, M. D. Clay, Trends Biotechnol. 2009, 27, 137-140.
96. S. G. Peisajovich, D. S. Tawfik, Nat. Methods 2007, 4, 991-994;
97. M. A. DePristo, HFSP Journal 2007, 1, 94-98;
98. J. D. Bloom, F. H. Arnold, Proc. Natl. Acad. Sci. USA 2009, 106, 9995-10000.
99. M. Eigen, J. McCaskill, P. Schuster, J. Phys. Chem. 1988, 92, 6881-6891.
100. S. Kurtovic, B. Mannervik, Biochemistry 2009, 48, 9330-9339.