Controlling the Regioselectivity of Baeyer–Villiger Monooxygenases by Mutation of Active-Site Residues

ChemBioChem

Volumn 18, Issue 16, 2017, Pages 1627-1638

  Balke, Kathleen ^a   Bäumgen, Marcus ^a   Bornscheuer, Uwe T ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Baeyer Villiger monooxygenases; enzyme catalysis; lactones; protein engineering; regioselectivity

Indexed keywords

ACETYL COENZYME A; AMINO ACID; CARVONE; CYCLOHEXANONE; CYCLOPENTANE DERIVATIVE; LACTONE; UNSPECIFIC MONOOXYGENASE; 2-OXO-DELTA(3)-4,5,5--TRIMETHYLCYCLOPENTENYL ACETYL-COA MONOOXYGENASE; BICYCLO(3,2,0)HEPT-2-EN-6-ONE; BRIDGED BICYCLO COMPOUNDS; DIHYDROCARVONE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; OXIDOREDUCTASE; TERPENE;

ACINETOBACTER; ARTHROBACTER; ARTICLE; BAEYER VILLIGER REACTION; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVE SITE; ENZYME SUBSTRATE COMPLEX; MUTATION; NONHUMAN; PRIORITY JOURNAL; REGIOSELECTIVITY; WILD TYPE; CHEMICAL STRUCTURE; CHEMISTRY; GENETICS; MOLECULAR DOCKING; PROTEIN ENGINEERING; SITE DIRECTED MUTAGENESIS; STEREOISOMERISM; SYNTHESIS;

BRIDGED BICYCLO COMPOUNDS; CATALYTIC DOMAIN; LACTONES; MOLECULAR DOCKING SIMULATION; MOLECULAR STRUCTURE; MONOTERPENES; MUTAGENESIS, SITE-DIRECTED; NADH, NADPH OXIDOREDUCTASES; NADP; PROTEIN ENGINEERING; STEREOISOMERISM;

EID: 85021374189     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201700223     Document Type: Article

References (74)

1. A. Baeyer, V. Villiger, Ber. Dtsch. Chem. Ges. 1899, 32, 3625–3633.
2. K. Balke, M. Kadow, H. Mallin, S. Sass, U. T. Bornscheuer, Org. Biomol. Chem. 2012, 10, 6249–6265;
3. H. Leisch, K. Morley, P. C. Lau, Chem. Rev. 2011, 111, 4165–4222;
4. D. E. Torres Pazmiño, H. M. Dudek, M. W. Fraaije, Curr. Opin. Chem. Biol. 2010, 14, 138–144.
5. G. de Gonzalo, M. D. Mihovilovic, M. W. Fraaije, ChemBioChem 2010, 11, 2208–2231.
6. Y. Hu, D. Dietrich, W. Xu, A. Patel, J. A. Thuss, J. Wang, W. B. Yin, K. Qiao, K. N. Houk, J. C. Vederas, Y. Tang, Nat. Chem. Biol. 2014, 10, 552–554.
7. D. E. Torres Pazmiño, R. Snajdrova, D. V. Rial, M. D. Mihovilovic, M. W. Fraaije, Adv. Synth. Catal. 2007, 349, 1361–1368;
8. H. M. Dudek, M. J. Fink, A. V. Shivange, A. Dennig, M. D. Mihovilovic, U. Schwaneberg, M. W. Fraaije, Appl. Microbiol. Biotechnol. 2014, 98, 4009–4020;
9. L. P. Parra, J. P. Acevedo, M. T. Reetz, Biotechnol. Bioeng. 2015, 112, 1354–1364;
10. M. Bocola, F. Schulz, F. Leca, A. Vogel, M. W. Fraaije, M. T. Reetz, Adv. Synth. Catal. 2005, 347, 979–986;
11. H. L. van Beek, G. d. Gonzalo, M. W. Fraaije, Chem. Commun. 2012, 48, 3288–3290.
12. A. Kirschner, U. T. Bornscheuer, Appl. Microbiol. Biotechnol. 2008, 81, 465–472;
13. M. T. Reetz, S. Wu, J. Am. Chem. Soc. 2009, 131, 15424–15432;
14. M. D. Mihovilovic, F. Rudroff, A. Winninger, T. Schneider, F. Schulz, M. T. Reetz, Org. Lett. 2006, 8, 1221–1224.
15. D. J. Opperman, M. T. Reetz, ChemBioChem 2010, 11, 2589–2596;
16. H. L. Van Beek, H. J. Wijma, L. Fromont, D. B. Janssen, M. W. Fraaije, FEBS Open Bio 2014, 4, 168–174;
17. S. Schmidt, M. Genz, K. Balke, U. T. Bornscheuer, J. Biotechnol. 2015, 214, 199–211.
18. H. M. Dudek, D. E. Torres Pazmino, C. Rodriguez, G. de Gonzalo, V. Gotor, M. W. Fraaije, Appl. Microbiol. Biotechnol. 2010, 88, 1135–1143;
19. N. M. Kamerbeek, M. W. Fraaije, D. B. Janssen, Eur. J. Biochem. 2004, 271, 2107–2116;
20. A. Beier, S. Bordewick, M. Genz, S. Schmidt, T. van den Bergh, C. Peters, H. J. Joosten, U. T. Bornscheuer, ChemBioChem 2016, 17, 2312–2315.
21. K. Balke, S. Schmidt, M. Genz, U. T. Bornscheuer, ACS Chem. Biol. 2016, 11, 38–43;
22. K. Chen, S. Wu, L. Zhu, C. Zhang, W. Xiang, Z. Deng, H. Ikeda, D. E. Cane, D. Zhu, Biochemistry 2016, 55, 6696–6704;
23. H. L. van Beek, E. Romero, M. W. Fraaije, ACS Chem. Biol. 2017, 12, 291–299.
24. D. Sheng, D. P. Ballou, V. Massey, Biochemistry 2001, 40, 11156–11167.
25. D. E. Torres Pazmiño, B. J. Baas, D. B. Janssen, M. W. Fraaije, Biochemistry 2008, 47, 4082–4093.
26. D. R. Kelly, C. J. Knowles, J. G. Mahdi, I. N. Taylor, M. A. Wright, J. Chem. Soc. Chem. Commun. 1995, 729–730.
27. H. L. van Beek, R. T. Winter, G. R. Eastham, M. W. Fraaije, Chem. Commun. 2014, 50, 13034–13036;
28. F. M. Ferroni, C. Tolmie, M. S. Smit, D. J. Opperman, ChemBioChem 2017, 18, 515–517;
29. S. Bisagni, B. Summers, S. Kara, R. Hatti-Kaul, G. Grogan, G. Mamo, F. Hollmann, Top. Catal. 2014, 57, 366–375.
30. J. Rehdorf, M. D. Mihovilovic, U. T. Bornscheuer, Angew. Chem. Int. Ed. 2010, 49, 4506–4508;
31. Angew. Chem. 2010, 122, 4609–4611.
32. M. J. Fink, R. Snajdrova, A. Winninger, M. D. Mihovilovic, Tetrahedron 2016, 72, 7241–7248.
33. P. Černuchová, M. D. Mihovilovic, Org. Biomol. Chem. 2007, 5, 1715–1719.
34. J. Rehdorf, M. D. Mihovilovic, M. W. Fraaije, U. T. Bornscheuer, Chem. Eur. J. 2010, 16, 9525–9535.
35. J. Rehdorf, A. Lengar, U. T. Bornscheuer, M. D. Mihovilovic, Bioorg. Med. Chem. Lett. 2009, 19, 3739–3743.
36. V. Alphand, A. Archelas, R. Furstoss, Tetrahedron Lett. 1989, 30, 3663–3664;
37. A. J. Carnell, S. M. Roberts, V. Sik, A. J. Willetts, J. Chem. Soc. Perkin Trans. 1 1991, 2385–2389;
38. M. D. Mihovilovic, P. Kapitan, Tetrahedron Lett. 2004, 45, 2751–2754;
39. R. Snajdrova, G. Grogan, M. D. Mihovilovic, Bioorg. Med. Chem. Lett. 2006, 16, 4813–4817;
40. A. Rioz-Martínez, G. de Gonzalo, D. E. T. Pazmino, M. W. Fraaije, V. Gotor, Eur. J. Org. Chem. 2009, 2526–2532.
41. N. Shimizu, D. Sakata, E. A. Schmelz, N. Mori, Y. Kuwahara, Proc. Natl. Acad. Sci. USA 2017, 114, 2616–2621.
42. B. P. Branchaud, C. T. Walsh, J. Am. Chem. Soc. 1985, 107, 2153–2161.
43. J. W. Song, E. Y. Jeon, D. H. Song, H. Y. Jang, U. T. Bornscheuer, D. K. Oh, J. B. Park, Angew. Chem. Int. Ed. 2013, 52, 2534–2537;
44. Angew. Chem. 2013, 125, 2594–2597.
45. N. Oberleitner, C. Peters, J. Muschiol, M. Kadow, S. Sass, T. Bayer, P. Schaaf, N. Iqbal, F. Rudroff, M. D. Mihovilovic, U. T. Bornscheuer, ChemCatChem 2013, 5, 3524–3528.
46. J. B. Wang, G. Li, M. T. Reetz, Chem. Commun. 2017, 53, 3916–3928.
47. P. C. Brzostowicz, D. M. Walters, S. M. Thomas, V. Nagarajan, P. E. Rouviere, Appl. Environ. Microbiol. 2003, 69, 334–342.
48. H. J. Ougham, D. G. Taylor, P. W. Trudgill, J. Bacteriol. 1983, 153, 140–152.
49. M. Kadow, K. Loschinski, S. Sass, M. Schmidt, U. T. Bornscheuer, Appl. Microbiol. Biotechnol. 2012, 96, 419;
50. H. Leisch, R. Shi, S. Grosse, K. Morley, H. Bergeron, M. Cygler, H. Iwaki, Y. Hasegawa, P. C. K. Lau, Appl. Environ. Microbiol. 2012, 78, 2200–2212.
51. F. Rudroff, M. J. Fink, R. Pydi, U. T. Bornscheuer, M. D. Mihovilovic, Monatsh. Chem. 2017, 148, 157–165.
52. S. D. Doig, P. J. Avenell, P. A. Bird, P. Gallati, K. S. Lander, G. J. Lye, R. Wohlgemuth, J. M. Woodley, Biotechnol. Prog. 2002, 18, 1039–1046;
53. C. V. F. Baldwin, R. Wohlgemuth, J. M. Woodley, Org. Process Res. Dev. 2008, 12, 660–665.
54. M. D. Mihovilovic, B. Muller, P. Stanetty, Eur. J. Org. Chem. 2002, 3711–3730.
55. M. L. Mascotti, M. J. Ayub, H. Dudek, M. K. Sanz, M. W. Fraaije, AMB Express 2013, 3, 33–43.
56. R. Gagnon, G. Grogan, M. S. Levitt, S. M. Roberts, P. W. H. Wan, A. J. Willetts, J. Chem. Soc. Perkin Trans. 1 1994, 2537–2543.
57. M. J. L. J. Fürst, S. Savino, H. M. Dudek, J. Rúben Gomez Castellanos, C. Gutiérrez de Souza, S. Rovida, M. W. Fraaije, A. Mattevi, J. Am. Chem. Soc. 2017, 139, 627–630.
58. E. Romero, J. R. G. Castellanos, A. Mattevi, M. W. Fraaije, Angew. Chem. Int. Ed. 2016, 55, 15852–15855;
59. Angew. Chem. 2016, 128, 16084–16087.
60. F. M. Ferroni, M. S. Smit, D. J. Opperman, J. Mol. Catal. B 2014, 107, 47–54.
61. C. Szolkowy, L. D. Eltis, N. C. Bruce, G. Grogan, ChemBioChem 2009, 10, 1208–1217.
62. B. D. Summers, M. Omar, T. O. Ronson, J. Cartwright, M. Lloyd, G. Grogan, Org. Biomol. Chem. 2015, 13, 1897–1903.
63. I. A. Mirza, B. J. Yachnin, S. Wang, S. Grosse, H. Bergeron, A. Imura, H. Iwaki, Y. Hasegawa, P. C. Lau, A. M. Berghuis, J. Am. Chem. Soc. 2009, 131, 8848–8854.
64. B. J. Yachnin, M. B. McEvoy, R. J. MacCuish, K. L. Morley, P. C. Lau, A. M. Berghuis, ACS Chem. Biol. 2014, 9, 2843–2851.
65. B. J. Yachnin, T. Sprules, M. B. McEvoy, P. C. K. Lau, A. M. Berghuis, J. Am. Chem. Soc. 2012, 134, 7788–7795.
66. R. Orru, H. M. Dudek, C. Martinoli, D. E. Torres Pazmino, A. Royant, M. Weik, M. W. Fraaije, A. Mattevi, J. Biol. Chem. 2011, 286, 29284–29291.
67. H. M. Dudek, G. de Gonzalo, D. E. Torres Pazmino, P. Stepniak, L. S. Wyrwicz, L. Rychlewski, M. W. Fraaije, Appl. Environ. Microbiol. 2011, 77, 5730–5738.
68. M. T. Reetz, F. Daligault, B. Brunner, H. Hinrichs, A. Deege, Angew. Chem. Int. Ed. 2004, 43, 4078–4081;
69. Angew. Chem. 2004, 116, 4170–4173.
70. M. T. Reetz, B. Brunner, T. Schneider, F. Schulz, C. M. Clouthier, M. M. Kayser, Angew. Chem. Int. Ed. 2004, 43, 4075–4078;
71. Angew. Chem. 2004, 116, 4167–4170.
72. P. B. Brondani, H. M. Dudek, C. Martinoli, A. Mattevi, M. W. Fraaije, J. Am. Chem. Soc. 2014, 136, 16966–16969.
73. C. T. Chung, S. L. Niemela, R. H. Miller, Proc. Natl. Acad. Sci. USA 1989, 86, 2172–2175.
74. L. C. P. Goncalves, D. Kracher, S. Milker, M. J. Fink, F. Rudroff, R. Ludwig, A. S. Bommarius, M. D. Mihovilovic, Adv. Synth. Catal. 2017, 359, 2121–2131.