Engineering of P450pyr hydroxylase for the highly regio- and enantioselective subterminal hydroxylation of alkanes

Angewandte Chemie - International Edition

Volumn 53, Issue 12, 2014, Pages 3120-3124

  Yang, Yi ^a   Liu, Ji ^a   Li, Zhi ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

biohydroxylation; Ci H activation; directed evolution; high throughput screening; P450 enzymes

Indexed keywords

ENANTIOSELECTIVITY; ENZYMES; PARAFFINS; REGIOSELECTIVITY;

BIOHYDROXYLATION; CI-H ACTIVATIONS; DIRECTED EVOLUTION; HIGH-THROUGHPUT SCREENING; P450 ENZYMES;

HYDROXYLATION;

ALKANES; MIXED FUNCTION OXYGENASES;

CHEMISTRY; GENETICS; HIGH-THROUGHPUT SCREENING ASSAYS; HYDROXYLATION; METABOLISM; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MUTATION; STEREOISOMERISM;

ALKANES; HIGH-THROUGHPUT SCREENING ASSAYS; HYDROXYLATION; MIXED FUNCTION OXYGENASES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MUTATION; STEREOISOMERISM;

EID: 84896324602     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201311091     Document Type: Article

References (47)

1. J. C. Lewis, P. S. Coelho, F. H. Arnold, Chem. Soc. Rev. 2011, 40, 2003-2021
2. Z. Li, D. Chang, Curr. Org. Chem. 2004, 8, 1647-1658.
3. S. Panke, M. Wubbolts, Curr. Opin. Chem. Biol. 2005, 9, 188-194.
4. K. Kamata, K. Yonehara, Y. Nakagawa, K. Uehara, N. Mizuno, Nat. Chem. 2010, 2, 478-483.
5. Z. Li, J. B. van Beilen, W. A. Duetz, A. Schmid, A. de Raadt, H. Griengl, B. Witholt, Curr. Opin. Chem. Biol. 2002, 6, 136-144
6. C. J. C. Whitehouse, S. G. Bell, L.-L. Wong, Chem. Soc. Rev. 2012, 41, 1218-1260
7. M. Merkx, D. A. Kopp, M. H. Sazinsky, J. L. Blazyk, J. Müller, S. J. Lippard, Angew. Chem. 2001, 113, 2860-2888
8. Angew. Chem. Int. Ed. 2001, 40, 2782-2807
9. D. J. Koch, M. M. Chen, J. B. van Beilen, F. H. Arnold, Appl. Environ. Microbiol. 2009, 75, 337-344.
10. M. T. Reetz, J. Org. Chem. 2009, 74, 5767-5778
11. U. T. Bornscheuer, G. W. Huisman, R. J. Kazlauskas, S. Lutz, J. C. Moore, K. Robins, Nature 2012, 485, 185-194
12. M. T. Reetz, Angew. Chem. 2011, 123, 144-182
13. Angew. Chem. Int. Ed. 2011, 50, 138-174
14. P. C. Cirino, F. H. Arnold, Curr. Opin. Chem. Biol. 2002, 6, 130-135.
15. C. J. Whitehouse, S. G. Bell, H. G. Tufton, R. J. Kenny, L. C. Ogilvie, L. L. Wong, Chem. Commun. 2008, 966-968
16. A. Dennig, N. Lulsdorf, H. Liu, U. Schwaneberg, Angew. Chem. 2013, 125, 8617-8620
17. Angew. Chem. Int. Ed. 2013, 52, 8459-8462.
18. O. Lentz, A. Feenstra, T. Habicher, B. Hauer, R. D. Schmid, V. B. Urlacher, ChemBioChem 2006, 7, 345-350
19. H. Venkataraman, S. B. A. de Beer, D. P. Geerke, N. P. E. Vermeulen, J. N. M. Commandeur, Adv. Synth. Catal. 2012, 354, 2172-2184.
20. S. Kille, F. E. Zilly, J. P. Acevedo, M. T. Reetz, Nat. Chem. 2011, 3, 738-743.
21. K. Zhang, B. M. Shafer, M. D. Demars, H. A. Stern, R. Fasan, J. Am. Chem. Soc. 2012, 134, 18695-18704.
22. D. Chang, B. Witholt, Z. Li, Org. Lett. 2000, 2, 3949-3952
23. Z. Li, H. J. Feiten, D. Chang, W. A. Duetz, J. B. van Beilen, B. Witholt, J. Org. Chem. 2001, 66, 8424-8430
24. D. L. Chang, H. J. Feiten, K. H. Engesser, J. B. van Beilen, B. Witholt, Z. Li, Org. Lett. 2002, 4, 1859-1862
25. D. L. Chang, H. J. Feiten, B. Witholt, Z. Li, Tetrahedron: Asymmetry 2002, 13, 2141-2147
26. W. Zhang, W. L. Tang, Z. S. Wang, Z. Li, Adv. Synth. Catal. 2010, 352, 3380-3390.
27. W. L. Tang, Z. Li, H. M. Zhao, Chem. Commun. 2010, 46, 5461-5463
28. S. Q. Pham, G. Pompidor, J. Liu, X. D. Li, Z. Li, Chem. Commun. 2012, 48, 4618-4620.
29. D. Böttcher, U. T. Bornscheuer, Curr. Opin. Microbiol. 2010, 13, 274-282
30. D. Scheps, S. Honda Malca, H. Hoffmann, B. M. Nestl, B. Hauer, Org. Biomol. Chem. 2011, 9, 6727-6733.
31. E. T. Farinas, U. Schwaneberg, A. Glieder, F. H. Arnold, Adv. Synth. Catal. 2001, 343, 601-606.
32. K. H. Halsey, L. A. Sayavedra-Soto, P. J. Bottomley, D. J. Arp, J. Bacteriol. 2006, 188, 4962-4969.
33. P. Meinhold, M. W. Peters, M. M. Chen, K. Takahashi, F. H. Arnold, ChemBioChem 2005, 6, 1765-1768
34. A. Glieder, E. T. Farinas, F. H. Arnold, Nat. Biotechnol. 2002, 20, 1135-1139
35. M. W. Peters, P. Meinhold, A. Glieder, F. H. Arnold, J. Am. Chem. Soc. 2003, 125, 13442-13450.
36. S. G. Bell, J. A. Stevenson, H. D. Boyd, S. Campbell, A. D. Riddle, E. L. Orton, L. L. Wong, Chem. Commun. 2002, 490-491.
37. A. Liese, T. Zelinski, M.-R. Kula, H. Kierkels, M. Karutz, U. Kragl, C. Wandrey, J. Mol. Catal. B 1998, 4, 91-99
38. Y. Hu, E. C. K. Lin, L. M. Pham, J. Cajica, C. M. Amantea, E. Okerberg, H. E. Brown, A. Fraser, L. Du, Y. Kohno, J. Ishiyama, J. W. Kozarich, K. R. Shreder, Bioorg. Med. Chem. Lett. 2013, 23, 1553-1556.
39. J. M. Wagner, C. J. McElhinny, Jr., A. H. Lewin, F. I. Carroll, Tetrahedron: Asymmetry 2003, 14, 2119-2125
40. S. K. Talluri, A. Sudalai, Tetrahedron 2007, 63, 9758-9763
41. F. X. Tavares, D. N. Deaton, A. B. Miller, L. R. Miller, L. L. Wright, Bioorg. Med. Chem. Lett. 2005, 15, 3891-3895.
42. Z. Li, L. Butikofer, B. Witholt, Angew. Chem. 2004, 116, 1730-1734
43. Angew. Chem. Int. Ed. 2004, 43, 1698-1702
44. Y. Z. Chen, W. L. Tang, J. Mou, Z. Li, Angew. Chem. 2010, 122, 5406-5411
45. Angew. Chem. Int. Ed. 2010, 49, 5278-5283.
46. H. Yamamoto, K. Kawada, A. Matsuyama, Y. Kobayashi, Biosci. Biotechnol. Biochem. 1999, 63, 1051-1055.
47. H. Yamamoto, M. Kudoh, Appl. Microbiol. Biotechnol. 2013, 97, 8087-8096.