Directed evolution of artificial metalloenzymes

Israel Journal of Chemistry

Volumn 55, Issue 1, 2015, Pages 51-60

  Ilie, Adriana ^a,b   Reetz, Manfred T ^a,b  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

artificial metalloenzymes; directed evolution; enantioselectivity; iterative saturation mutagenesis; transition metal catalysis

Indexed keywords

EID: 84921661354     PISSN: 00212148     EISSN: 18695868     Source Type: Journal    
DOI: 10.1002/ijch.201400087     Document Type: Review

References (93)

1. Recent reviews of directed evolution
2. Protein Engineering Handbook, Vol.?1-2, (Eds.:, S. Lutz, U.?T. Bornscheuer,), Wiley-VCH, Weinheim, 2009
3. M. B. Quin, C. Schmidt-Dannert, ACS Catal. 2011, 1, 1017-1021
4. E. M. Brustad, F. H. Arnold, Curr. Opin. Chem. Biol. 2011, 15, 201-210
5. C. Jäckel, D. Hilvert, Curr. Opin. Biotechnol. 2010, 21, 753-759
6. N. J. Turner, Nat. Chem. Biol. 2009, 5, 567-573
7. A. S. Bommarius, J. K. Blum, M. J. Abrahamson, Curr. Opin. Chem. Biol. 2011, 15, 194-200
8. A. V. Shivange, J. Marienhagen, H. Mundhada, A. Schenk, U. Schwaneberg, Curr. Opin. Chem. Biol. 2009, 13, 19-25
9. S. Bershtein, D. S. Tawfik, Curr. Opin. Chem. Biol. 2008, 12, 151-158
10. N. U. Nair, C. A. Denard, H. Zhao, Curr. Org. Chem. 2010, 14, 1870-1882
11. R. M. P. Siloto, R. J. Weselake, Biocatal. Agric. Biotechnol. 2012, 1, 181-189
12. J. Liang, J. Lalonde, B. Borup, V. Mitchell, E. Mundorff, N. Trinh, D. A. Kochrekar, R. N. Cherat, G. G. Pai, Org. Process Res. Dev. 2010, 14, 193-198
13. M. T. Reetz, in Enzyme Catalysis in Organic Synthesis, 3rd Edition, Vol.?1, (Eds.:, K. Drauz, H. Gröger, O. May,), Wiley-VCH, Weinheim, 2012, pp.? 119-190.
14. Reviews of directed evolution of stereoselective enzymes
15. M. T. Reetz, Angew. Chem. Int. Ed. 2011, 50, 138-174
16. M. T. Reetz, in Manual of Industrial Microbiology and Biotechnology, 3rd Edition (Eds.:, R.?H. Baltz, A.?L. Demain, J.?E. Davies, A.?T. Bull, B. Junker, L. Katz, L.?R. Lynd, P. Masurekar, C.?D. Reeves, H. Zhao,), ASM Press, Washington, 2010, pp.? 466-479.
17. Enzyme Catalysis in Organic Synthesis, 3rd Edition (Eds.:, K. Drauz, H. Gröger, O. May,), Wiley-VCH, Weinheim, 2012
18. M. T. Reetz, J. Am. Chem. Soc. 2013, 135, 12480-12496.
19. Enzyme Assays, High-throughput Screening, Genetic Selection and Fingerprinting (Ed.:, J.-J. Reymond,), Wiley-VCH, Weinheim, 2006.
20. M. T. Reetz, M. H. Becker, H.-W. Klein, D. Stöckigt, Angew. Chem. Int. Ed. 1999, 38, 1758-1761
21. M. T. Reetz, Angew. Chem. Int. Ed. 2001, 40, 284-310.
22. M. T. Reetz, J. D. Carballeira, Nat. Protoc. 2007, 2, 891-903.
23. W. M. Patrick, A. E. Firth, Biomol. Eng. 2005, 22, 105-112; see also
24. M. Denault, J. N. Pelletier, in Protein Engineering Protocols, Vol.?352 (Eds.:, K.?M. Arndt, K.?M. Müller,), Humana Press, Totowa, 2007, pp.? 127-154
25. C. Acevedo-Rocha, S. Höbenreich, M. T. Reetz, Methods Molec. Biol. 2014, 1179, 103-128.
26. Y. Nov, Appl. Environ. Microbiol. 2012, 78, 258-262.
27. M. T. Reetz, D. Kahakeaw, R. Lohmer, ChemBioChem 2008, 9, 1797-1804
28. M. T. Reetz, S. Prasad, J. D. Carballeira, Y. Gumulya, M. Bocola, J. Am. Chem. Soc. 2010, 132, 9144-9152.
29. M. T. Reetz, patent WO 92,18645, 2001.
30. Early studies of artificial metalloenzymes and other hybrid catalysts
31. D. Qi, C.-M. Tann, D. Haring, M. D. Distefano, Chem. Rev. 2001, 101, 3081-3111
32. L. Polgar, M. L. Bender, J. Am. Chem. Soc. 1966, 88, 3153-3154
33. P. G. Schultz, Science 1988, 240, 426-433
34. K. Khumtaveeporn, G. DeSantis, J. B. Jones, Tetrahedron: Asymmetry 1999, 10, 2563-2572
35. H. B. Smith, F. C. Hartman, J. Biol. Chem. 1988, 263, 4921-4925
36. K. M. Nicholas, P. Wentworth ? Jr., C. W. Harwig, A. D. Wentworth, A. Shafton, K. D. Janda, Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 2648-2653
37. I. Hamachi, S. Shinkai, Eur. J. Org. Chem. 1999, 539-549
38. Y. Lu, J. S. Valentine, Curr. Opin. Struct. Biol. 1997, 7, 495-500
39. Y. Lu, S. M. Berry, T. D. Pfister, Chem. Rev. 2001, 101, 3047-3080
40. E. T. Kaiser, Angew. Chem. Int. Ed. Engl. 1988, 27, 913-922
41. C. T. Choma, J. D. Lear, M. J. Nelson, P. L. Dutton, D. E. Robertson, W. F. DeGrado, J. Am. Chem. Soc. 1994, 116, 856-865.
42. M. T. Reetz, Tetrahedron 2002, 58, 6595-6602
43. M. T. Reetz, M. Rentzsch, A. Pletsch, M. Maywald, P. Maiwald, J. J.-P. Peyralans, A. Maichele, Y. Fu, N. Jiao, F. Hollmann, R. Mondière, A. Taglieber, Tetrahedron 2007, 63, 6404-6414
44. A. Pletsch, Dr. rer. nat. Dissertation, Ruhr-Universität Bochum, Germany, 2004.
45. B. Cornils, W. A. Herrmann, Aqueous-Phase Organometallic Catalysis, Wiley-VCH, Weinheim, 2006.
46. M. T. Reetz, in Topics in Organometallic Chemistry, Vol.?25, (Ed.:, T.?R. Ward,), Springer-Verlag, Berlin, Heidelberg, 2009, pp.? 63-92.
47. T. Ueno, T. Koshiyama, M. Ohashi, K. Kondo, M. Kono, A. Suzuki, T. Yamane, Y. Watanabe, J. Am. Chem. Soc. 2005, 127, 6556-6562
48. T. Ueno, S. Abe, N. Yokoi, W. Watanabe, Coord. Chem. Rev. 2007, 251, 2717-2731
49. A. Mahammed, Z. Gross, J. Am. Chem. Soc. 2005, 127, 2883-2887
50. Y. Lu, N. Yeung, N. Sieracky, N. M. Marshall, Nature 2009, 460, 855-862
51. Y. Lu, Curr. Opin. Chem. Biol. 2005, 9, 118-126
52. P. D. Barker, Curr. Opin. Struct. Biol. 2003, 13, 490-499
53. H. S. Lee, G. Spraggon, P. G. Schultz, F. Wang, J. Am. Chem. Soc. 2009, 131, 2481-2483
54. C. A. Kruithof, M. A. Casado, G. Guillena, M. R. Egmond, A. van?de?Kerk-van?Hoof, A. J. R. Heck, R. J. M. Klein Gebbink, G. van?Koten, Chem. Eur. J. 2005, 11, 6869-6877
55. A. L. Eckermann, K. D. Barker, M. R. Hartings, M. A. Ratner, T. J. Meade, J. Am. Chem. Soc. 2005, 127, 11880-11881
56. M. T. Reetz, N. Jiao, Angew. Chem. 2006, 118, 2476-2479
57. Angew. Chem. Int. Ed. 2006, 45, 2416-2419
58. M. T. Reetz, Chem. Rec. 2012, 12, 391-406
59. V. Köhler, Y. M. Wilson, M. Dürrenberger, D. Ghislieri, E. Churakova, T. Quinto, L. Knörr, D. Häussinger, F. Hollmann, N. J. Turner, T. R. Ward, Nat. Chem. 2013, 5, 93-99
60. A. Roy, I. Sarrou, M. D. Vaughn, A. V. Astashkin, G. Ghirlanda, Biochemistry 2013, 52, 7586-7594
61. M. Venanzi, S. Cianfanelli, A. Palleshi, J. Pept. Sci. 2014, 20, 36-45
62. J. Bos, G. Roelfes, Curr. Opin. Chem. Biol. 2014, 19, 135-143
63. I. D. Petrik, J. Liu, Y. Lu, Curr. Opin. Chem. Biol. 2014, 19, 67-75.
64. M. E. Wilson, G. M. Whitesides, J. Am. Chem. Soc. 1978, 100, 306-307.
65. P. C. Weber, D. H. Ohlendorf, J. J. Wendoloski, F. R. Salemme, Science 1989, 243, 85-88.
66. S.-C. Wu, M. H. Qureshi, S. L. Wong, Protein Expression Purif. 2002, 24, 348-356
67. S.-C. Wu, S.-L. Wong, Appl. Environ. Microbiol. 2002, 68, 1102-1108.
68. M. T. Reetz, J. J.-P. Peyralans, A. Maichele, Y. Fu, M. Maywald, Chem. Commun. 2006, 4318-4320.
69. C. M. Thomas, T. R. Ward, Chem. Soc. Rev. 2005, 34, 337-346
70. T. R. Ward, Chem. Eur. J. 2005, 11, 3798-3804
71. G. Klein, N. Humbert, J. Gradinaru, A. Ivanova, F. Gilardoni, U. E. Rusbandi, T. R. Ward, Angew. Chem. Int. Ed. 2005, 44, 7764-7767
72. C. Letondor, A. Pordea, N. Humbert, A. Ivanova, S. Mazurek, M. Novic, T. R. Ward, J. Am. Chem. Soc. 2006, 128, 8320-8328
73. K. Hyster, L. Knörr, T. R. Ward, T. Rovis, Science 2012, 338, 500-503
74. M. Durrenberger, T. R. Ward, Curr. Opin. Chem. Biol. 2014, 19C, 99-106; see also general review of the application of the biotin/streptavidin-technology in chemical and biological applications
75. C. Dundas, D. Demonte, S. Park, Appl. Microbiol. Biotechnol. 2013, 97, 9343-9353.
76. S. Rakshit, C. Grohmann, T. Besset, F. Glorius, J. Am. Chem. Soc. 2011, 133, 2350-2353
77. N. Guimond, S. I. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 2011, 133, 6449-6457.
78. E. S. Nogueira, T. Schleier, M. Dürrenberger, K. Ballmer-Hofer, T. R. Ward, R. Jaussi, Protein Expression Purif. 2014, 93, 54-62.
79. M. Creus, A. Pordea, T. Rossel, A. Sardo, C. Letondor, A. Ivanova, I. Letrong, R. E. Stenkamp, T. R. Ward, Angew. Chem. Int. Ed. 2008, 47, 1400-1404.
80. R. Noyori, Angew. Chem. Int. Ed. 2002, 41, 2008-2022.
81. L. A. Chen, W. Xu, B. Huang, J. Ma, L. Wang, J. Xi, K. Harms, L. Gong, E. Meggers, J. Am. Chem. Soc. 2013, 135, 10598-10601.
82. M. T. Reetz, M. Rentzsch, A. Pletsch, A. Taglieber, F. Hollmann, R. J. G. Mondière, N. Dickmann, B. Höcker, S. Cerrone, M. C. Haeger, R. Sterner, ChemBioChem 2008, 9, 552-564.
83. A. Douangamath, M. Walker, S. Beismann-Driemeyer, M. C. Vega-Fernandez, R. Sterner, M. Wilmanns, Structure 2002, 10, 185-193
84. S. Beismann-Driemeyer, R. Sterner, J. Biol. Chem. 2001, 276, 20387-20396.
85. D. Lang, R. Thoma, M. Henn-Sax, R. Sterner, M. Wilmanns, Science 2000, 289, 1546-1550.
86. J. Podtetenieff, A. Taglieber, E. Bill, E. J. Reijerse, M. T. Reetz, Angew. Chem. Int. Ed. 2010, 49, 5151-5155.
87. S. D. Khare, Y. Kipnis, P. Jr Greisen, R. Takeuchi, Y. Ashani, M. Goldsmith, Y. Song, J. L. Gallaher, I. Silman, H. Leader, J. L. Sussman, B. L. Stoddard, D. S. Tawfik, D. Baker, Nat. Chem. Biol. 2012, 8, 294-300
88. G. Kiss, N. Çelebi-Ölçüm, R. Moretti, D. Baker, K. N. Houk, Angew. Chem. Int. Ed. 2013, 52, 5700-5725.
89. T. Dudev, C. Lim, Annu. Rev. Biophys. 2008, 37, 97-116
90. A. J. Mulholland, Biochem. Soc. Trans. 2008, 36, 22-26
91. S. Shaik, S. Cohen, Y. Wang, H. Chen, D. Kumar, W. Thiel, Chem. Rev. 2010, 110, 949-1017
92. A. Barrozo, R. Borstnar, G. Marloie, S. C. L. Kamerlin, Int. J. Mol. Sci. 2012, 13, 12428-12460
93. M. P. Frushicheva, M. J. L. Mills, P. Schopf, M. K. Singh, R. B. Prasad, A. Warshel, Curr. Opin. Chem. Biol. 2014, 21C, 56-62.