Stereo-controlled asymmetric bioreduction of α,β-dehydroamino acid derivatives

Advanced Synthesis and Catalysis

Volumn 353, Issue 7, 2011, Pages 1169-1173

  Stueckler, Clemens ^a   Winkler, Christoph K ^a   Hall, Mélanie ^a   Hauer, Bernhard ^b,c   Bonnekessel, Melanie ^b   Zangger, Klaus ^a   Faber, Kurt ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b BASF SE   (Germany)

^c UNIVERSITY OF STUTTGART   (Germany)

Author keywords

asymmetric bioreduction; dehydroamino acids; ene reductase; old yellow enzyme; stereocontrol

Indexed keywords

EID: 79955920111     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100042     Document Type: Article

References (46)

1. For homogeneous catalysts see R. Noyori, Angew. Chem. 2002, 114, 2108-2123
2. Angew. Chem. Int. Ed. 2002, 41, 2008-2022
3. W. S. Knowles, Angew. Chem. 2002, 114, 2096-2107
4. Angew. Chem. Int. Ed. 2002, 41, 1998-2007.
5. For organocatalysts see J. W. Yang, M. T. Hechavarria Fonseca, N. Vignola, B. List, Angew. Chem. 2005, 117, 110-112
6. Angew. Chem. Int. Ed. 2005, 44, 108-110
7. S. G. Quellet, J. B. Tuttle, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 32-33.
8. R. E. Williams, N. C. Bruce, Microbiology 2002, 148, 1607-1614.
9. R. Stuermer, B. Hauer, M. Hall, K. Faber, Curr. Opin. Chem. Biol. 2007, 11, 203-213
10. M. Hall, Y. Yanto, A. S. Bommarius, 'in: The Encyclopedia of Industrial Biotechnology: Bioprocess, Bioseparation, and Cell Technology, (Ed.:, M. Flickinger,), Wiley, 2010, pp 2234-2247
11. H. S. Toogood, J. M. Gardiner, N. S. Scrutton, ChemCatChem 2010, 2, 892-914.
12. O. Warburg, W. Christian, Biochem. Z. 1933, 266, 377-411.
13. For studies on the substrate-tolerance see M. Hall, C. Stueckler, W. Kroutil, P. Macheroux, K. Faber, Angew. Chem. 2007, 119, 4008-4011
14. Angew. Chem. Int. Ed. 2007, 46, 3934-3937
15. 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
16. M. Hall, C. Stueckler, B. Hauer, R. Stuermer, T. Friedrich, M. Breuer, W. Kroutil, K. Faber, Eur. J. Org. Chem. 2008, 1511-1516
17. N. J. Mueller, C. Stueckler, B. Hauer, N. Baudendistel, H. Housden, N. C. Bruce, K. Faber, Adv. Synth. Catal. 2010, 352, 387-394
18. A. Fryszkowska, H. Toogood, M. Sakuma, J. M. Gardiner, G. M. Stephens, N. S. Scrutton, Adv. Synth. Catal. 2009, 351, 2976-2990
19. D. J. Bougioukou, S. Kille, A. Taglieber, M. T. Reetz, Adv. Synth. Catal. 2009, 351, 3287-3305
20. J. F. Chaparro-Riggers, T. A. Rogers, E. Vazquez-Figueroa, K. M. Polizzi, A. S. Bommarius, Adv. Synth. Catal. 2007, 349, 1521-1531.
21. For applications of OYEs to asymmetric synthesis see B. Kosjek, F. J. Fleitz, P. G. Dormer, J. T. Kuethe, P. N. Devine, Tetrahedron: Asymmetry 2008, 19, 1403-1406
22. C. Stueckler, M. Hall, H. Ehammer, E. Pointner, W. Kroutil, P. Macheroux, K. Faber, Org. Lett, 2007, 9, 5409-5411
23. C. Stueckler, N. J. Mueller, C. K. Winkler, S. M. Glueck, K. Gruber, G. Steinkellner K. Faber, Dalton Trans. 2010, 39, 8472-8476
24. 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
25. M. Utaka, S. Konishi, A. Mizuoka, T. Ohkubo, T. Sakai, S. Tsuboi, A. Tekeda, J. Org. Chem. 1989, 54, 4989-4992
26. A. Mueller, B. Hauer, B. Rosche, Biotechnol. Bioeng. 2007, 98, 22
27. C. Stueckler, C. K. Winkler, M. Bonnekessel, K. Faber, Adv. Synth. Catal. 2010, 352, 2663-2666.
28. C. K. Winkler, C. Stueckler, N. J. Mueller, D. Pressnitz, K. Faber, Eur. J. Org. Chem. 2010, 6354-6358.
29. While Rh-based catalysts showed high stereoselectivities, Ru-catalysts gave lower ees and Ir was used for branched dehydroamino acids, see C. Nájera, J. M. Sansano, Chem. Rev. 2007, 107, 4584-4671
30. W. Tang, A. G. Capacci, A. White, S. Ma, S. Rodriguez, B. Qu, J. Savoie, N. D. Patel, X. Wei, N. Haddad, N. Grinberg, N. K. Yee, D. Krishnamurthy, C. H. Senanayake, Org. Lett. 2010, 12, 1104-1107.
31. U. E. Rusbandi, C. Lo, M. Skander, A. Ivanova, M. Creus, N. Humbert, T. R. Ward, Adv. Synth. Catal. 2007, 349, 1923-1930
32. G. Klein, N. Humbert, J. Gradinaru, A. Ivanova, F. Gilardoni, U. E Rusbandi, T. R. Ward, Angew. Chem. 2005, 117, 7942-7945
33. Angew. Chem. Int. Ed. 2005, 44, 7764-7767.
34. M. A. Swiderska, J. D. Stewart, Org. Lett. 2006, 8, 6131-6133.
35. A. Fryszkowska, K. Fisher, J. M. Gardiner, G. M. Stephens, Org. Biomol. Chem. 2010, 8, 533-535.
36. K. Saito, D. J. Thiele, M. Davio, O. Lockridge, V. Massey, J. Biol. Chem. 1991, 266, 20720-20724
37. K. Stott, K. Saito, D. J. Thiele, V. Massey, J. Biol. Chem. 1993, 268, 6097-6106
38. Y. S. Niino, S. Chakraborty, B. J. Brown, V. Massey, J. Biol. Chem. 1995, 270, 1983-1991.
39. C. Breithaupt, R. Kurzbauer, H. Lilie, A. Schaller, J. Strassner, R. Huber, P. Macheroux, T. Clausen, Proc. Natl. Acad. Sci. USA 2006, 103, 14337-14342.
40. K. Kitzing, T. B. Fitzpatrick, C. Wilken, J. Sawa, G. P. Bourenkov, P. Macheroux, T. Clausen, J. Biol. Chem. 2005, 280, 27904-27913.
41. A. Müller, B. Hauer, B. Rosche, Biotechnol. Bioeng. 2007, 98, 22-29.
42. D. J. Bougioukou, J. D. Stewart, J. Am. Chem. Soc. 2008, 130, 7655-7658
43. S. K. Padhi, D. J. Bougioukou, J. D. Stewart, J. Am. Chem. Soc. 2009, 131, 3271-3280.
44. P. A. Karplus, K. M. Fox, V. Massey, FASEB J. 1995, 9, 1518-1526
45. R. M. Kohli, V. Massey, J. Biol. Chem. 1998, 273, 32763-32770.
46. F296 and S297 are part of the binding pocket directly above the si-face of the flavin and are thus very close to the substrate (<4Å), as determined in the crystal structure of OYE1 (PDB DOI:10.2210/pdb1oyb/pdb) taking the docked inhibitor p-hydroxybenzaldehyde as substrate mimic by using PyMol (The PyMOL Molecular Graphics System, Version 1.3, Schrödinger, LLC); see also K. M. Fox, P. A. Karplus, Structure 1994, 2, 1089-1105.