Whole-Cell-Catalyzed Multiple Regio- and Stereoselective Functionalizations in Cascade Reactions Enabled by Directed Evolution

Angewandte Chemie - International Edition

Volumn 55, Issue 39, 2016, Pages 12026-12029

  Li, Aitao ^a,b   Ilie, Adriana ^a,b   Sun, Zhoutong ^a,b   Lonsdale, Richard ^a,b   Xu, Jian He ^c   Reetz, Manfred T ^a,b  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

^c EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

cascade reactions; C H activation; directed evolution; enantioselectivity; P450 monooxygenase

Indexed keywords

CYCLOHEXANE; ENANTIOSELECTIVITY; ENZYMES; ESCHERICHIA COLI;

ALCOHOL DEHYDROGENASE; CASCADE REACTIONS; DIRECTED EVOLUTION; FUNCTIONALIZATIONS; INTERMEDIATE PRODUCT; MONOOXYGENASES; STEREO-SELECTIVE; WILD-TYPE ENZYMES;

STEREOSELECTIVITY;

EID: 84992088951     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201605990     Document Type: Article

References (43)

1. E. J. Corey, The Logic of Chemical Synthesis, Wiley, New York, 1995;
2. C. Grondal, M. Jeanty, D. Enders, Nat. Chem. 2010, 2, 167–178;
3. K. C. Nicolaou, J. S. Chen, Chem. Soc. Rev. 2009, 38, 2993–3009;
4. Catalytic Cascade Reactions (Eds.: P.-F. Xu, W. Wang), Wiley, New York, 2014.
5. N. J. Turner, E. O'Reilly, Nat. Chem. Biol. 2013, 9, 285–288.
6. Enzyme Catalysis in Organic Chemistry (Eds.: K. Drauz, H. Gröger, O. May), Wiley-VCH, Weinheim, 2012;
7. P. Both, H. Busch, P. P. Kelly, F. G. Mutti, N. J. Turner, S. L. Flitsch, Angew. Chem. Int. Ed. 2016, 55, 1511–1513;
8. Angew. Chem. 2016, 128, 1533–1536;
9. T. Bayer, S. Milker, T. Wiesinger, F. Rudroff, M. D. Mihovilovic, Adv. Synth. Catal. 2015, 357, 1587–1618;
10. F. G. Mutti, T. Knaus, N. S. Scrutton, M. Breuer, N. J. Turner, Science 2015, 349, 1525–1529;
11. L. Skalden, C. Peters, J. Dickerhoff, A. Nobili, H. J. Joosten, K. Weisz, M. Hohne, U. T. Bornscheuer, ChemBioChem 2015, 16, 1041–1045;
12. S. Riva, W.-D. Fessner, Cascade Biocatalysis, Wiley-VCH, Weinheim, 2014;
13. S. K. Wu, Y. Z. Chen, Y. Xu, A. T. Li, Q. S. Xu, A. Glieder, Z. Li, ACS Catal. 2014, 4, 409–420;
14. H. Gröger, W. Hummel, Curr. Opin. Chem. Biol. 2014, 19, 171–179;
15. R. Agudo, M. T. Reetz, Chem. Commun. 2013, 49, 10914–10916;
16. E. Ricca, B. Brucher, J. H. Schrittwieser, Adv. Synth. Catal. 2011, 353, 2239–2262;
17. S. K. Wu, Y. Zhou, T. W. Wang, H. P. Too, D. I. C. Wang, Z. Li, Nat. Commun. 2016, 7, 11917.
18. A. S. Bommarius, Annu. Rev. Chem. Biomol. 2015, 6, 319–345;
19. C. A. Denard, H. Q. Ren, H. M. Zhao, Curr. Opin. Chem. Biol. 2015, 25, 55–64;
20. M. T. Reetz, Angew. Chem. Int. Ed. 2011, 50, 138–174;
21. Angew. Chem. 2011, 123, 144–182;
22. E. M. Brustad, F. H. Arnold, Curr. Opin. Chem. Biol. 2011, 15, 201–210;
23. C. Jäckel, D. Hilvert, Curr. Opin. Biotechnol. 2010, 21, 753–759;
24. N. J. Turner, Nat. Chem. Biol. 2009, 5, 568–574;
25. S. Lutz, U. T. Bornscheuer, Protein Engineering Handbook, Wiley-VCH, Weinheim, 2009.
26. H. M. Girvan, A. W. Munro, Curr. Opin. Chem. Biol. 2016, 31, 136–145;
27. P. R. Ortiz de Montellano, Chem. Rev. 2010, 110, 932–948.
28. D. C. Haines, D. R. Tomchick, M. Machius, J. A. Peterson, Biochemistry 2001, 40, 13456–13465;
29. A. Glieder, E. T. Farinas, F. H. Arnold, Nat. Biotechnol. 2002, 20, 1135–1139.
30. S. Staudt, E. Burda, C. Giese, C. A. Muller, J. Marienhagen, U. Schwaneberg, W. Hummel, K. Drauz, H. Gröger, Angew. Chem. Int. Ed. 2013, 52, 2359–2363;
31. Angew. Chem. 2013, 125, 2415–2419.
32. Z. Sun, Y. Wikmark, J. E. Bäckvall, M. T. Reetz, Chem. Eur. J. 2016, 22, 5046–5054.
33. Z. Sun, R. Lonsdale, L. Wu, G. Li, A. T. Li, J. Wang, J. Zhou, M. T. Reetz, ACS Catal. 2016, 6, 1590–1597;
34. Z. Sun, R. Lonsdale, A. Ilie, G. Li, J. Zhou, M. T. Reetz, ACS Catal. 2016, 6, 1598–1605.
35. R. Agudo, G. D. Roiban, R. Lonsdale, A. Ilie, M. T. Reetz, J. Org. Chem. 2015, 80, 950–956.
36. S. Kille, F. E. Zilly, J. P. Acevedo, M. T. Reetz, Nat. Chem. 2011, 3, 738–743;
37. C. J. C. Whitehouse, S. G. Bell, L. L. Wong, Chem. Soc. Rev. 2012, 41, 1218–1260;
38. R. Bernhardt, V. B. Urlacher, Appl. Microbiol. 2014, 98, 6185–6203;
39. R. Fasan, ACS Catal. 2012, 2, 647–666.
40. Y. J. Yan, C. C. Lee, J. C. Liao, Org. Biomol. Chem. 2009, 7, 3914–3917;
41. J. D. Zhang, T. T. Xu, Z. Li, Adv. Synth. Catal. 2013, 355, 3147–3153;
42. S. Ui, Y. Takusagawa, T. Sato, T. Ohtsuki, A. Mimura, M. Ohkuma, T. Kudo, Lett. Appl. Microbiol. 2004, 39, 533–537.
43. P. Hoyos, J. V. Sinisterra, F. Molinari, A. R. Alcantara, P. D. De Maria, Acc. Chem. Res. 2010, 43, 288–299.