Stereospecific reduction of methyl o-chlorobenzoylformate at 300 g·L -1 without additional cofactor using a carbonyl reductase mined from Candida glabrata

Advanced Synthesis and Catalysis

Volumn 354, Issue 9, 2012, Pages 1765-1772

  Ma, Hongmin ^a   Yang, Linlin ^b   Ni, Yan ^a   Zhang, Jie ^a   Li, Chun Xiu ^a   Zheng, Gao Wei ^a   Yang, Huaiyu ^b   Xu, Jian He ^a  

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

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

bioinformatics; biotransformations; cofactors; oxidoreductases

Indexed keywords

EID: 84862513176     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100366     Document Type: Article

References (62)

1. K. Nakamura, R. Yamanaka, T. Matsuda, T. Harada, Tetrahedron: Asymmetry 2003, 14, 2659-2681
2. K. Nakamura, T. Matsuda, Curr. Org. Chem. 2006, 10, 1217-1246
3. S. Panke, M. Wubbolts, Curr. Opin. Chem. Biol. 2005, 9, 188-194
4. W. Kroutil, H. Mang, K. Edegger, K. Faber, Curr. Opin. Chem. Biol. 2004, 8, 120-126
5. J.-H. Tao, J.-H. Xu, Curr. Opin. Chem. Biol. 2009, 13, 43-50
6. R. N. Patel, Adv. Synth. Catal. 2001, 343, 527-546
7. Y. Ni, J.-H. Xu, Biotechnol. Adv. 2011, doi: 10.1016/j.biotechadv.2011. 10.007.
8. I. Kaluzna, T. Matsuda, A. Sewell, J. Stewart, J. Am. Chem. Soc. 2004, 126, 12827-12832
9. Y. Ni, C.-X. Li, H.-M. Ma, J. Zhang, J.-H. Xu, Appl. Microbiol. Biotechnol. 2011, 89, 1111-1118
10. D.-M. Zhu, H. Malik, L. Hua, Tetrahedron: Asymmetry 2006, 17, 3010-3014.
11. A. Knietsch, T. Waschkowitz, S. Bowien, A. Henneee, R. J. Daniel, J. Mol. Microbiol. Biotechnol. 2003, 5, 46-56.
12. T. Matsuda, R. Yamanaka, K. Nakamura, Tetrahedron: Asymmetry 2009, 20, 513-557.
13. A. Bousquet, A. Musolino, PCT Int. Appl. WO9918110 A1, 1999.
14. K. Mitsuhashi, H. Yamamoto, Eur. Pat. Appl. EP1316613 A2, 2003.
15. A. Glieder, R. Weis, W. Skranc, P. Poechlauer, I. Dreveny, S. Majer, M. Wubbolts, H. Schwab, K. Gruber, Angew. Chem. 2003, 115, 4963
16. Angew. Chem. Int. Ed. 2003, 42, 4815-4818
17. L. M. van Langen, R. P. Selassa, F. van Rantwijk, R. A. Sheldon, Org. Lett. 2005, 7, 327-329.
18. Z.-J. Zhang, J. Pan, J.-F. Liu, J.-H. Xu, J. Biotechnol. 2011, 152, 24-29
19. C.-S. Zhang, Z.-J. Zhang, C.-X. Li, H.-L. Yu, G. W. Zheng, J.-H. Xu, Appl. Microbiol. Biotechnol. DOI: 10.1007/s00253- 012 -3993-4.
20. J.-P. Genet, S. Juge, J.-A. Laffitte, C. Pinel, S. Mallart, PCT Int. Appl. WO9401390 A1, 1994
21. Y. Sun, X. Wan, J. Wang, Q. Meng, H. Zhang, L. Jiang, Z. Zhang, Org. Lett. 2005, 7, 5425-5427.
22. T. Ema, Y. Sugiyama, M. Fukumoto, H. Moriya, J.-N. Cui, T. Sakai, M. Utaka, J. Org. Chem. 1998, 63, 4996-5000
23. T. Ema, H. Moriya, T. Kofukuda, T. Ishida, K. Maehara, M. Utaka, T. Sakai, J. Org. Chem. 2001, 66, 8682-8684
24. T. Ema, H. Yagasaki, N. Okita, K. Nishikawa, T. Korenaga, T. Sakai, Tetrahedron: Asymmetry 2005, 16, 1075-1078
25. T. Ema, H. Yagasaki, N. Okita, M. Takeda, T. Sakai, Tetrahedron 2006, 62, 6143-6149.
26. T. Ema, N. Okita, S. Ide, T. Sakai, Org. Biomol. Chem. 2007, 5, 1175-1176
27. T. Ema, S. Ide, N. Okita, T. Sakai, Adv. Synth. Catal. 2008, 350, 2039-2044.
28. F. Hollmann, I. W. C. E. Arends, K. Buehler, ChemCatChem 2010, 2, 762-782
29. N. St. Clair, Y.-F. Wang, A. L. Margolin, Angew. Chem. 2000, 112, 388-391
30. Angew. Chem. Int. Ed. 2000, 39, 380-383
31. W. Stampfer, B. Kosjek, C. Moitzi, W. Kroutil, K. Faber, Angew. Chem. 2002, 114, 1056-1059
32. Angew. Chem. Int. Ed. 2002, 41, 1014-1017.
33. G. Iwasaki, R. Kimura, N. Numao, K. Kondo, Chem. Pharm. Bull. 1989, 37, 280-283.
34. M. Kataoka, K. Yamamoto, H. Kawabata, M. Wada, K. Kita, H. Yanase, S. Shimizu, Appl. Microbiol. Biotechnol. 1999, 51, 486-490
35. J. Grunwald, B. Wirz, M. P. Scollar, A. M. Klibanov, J. Am. Chem. Soc. 1986, 108, 248-258
36. W. R. Shieh, A. S. Gopalan, C. J. Sih, J. Am. Chem. Soc. 1985, 107, 2993-2994
37. C.-H. Wong, D. G. Drueckhammer, H. M. Sweers, J. Am. Chem. Soc. 1985, 107, 4028-4031
38. B. Zhou, A. S. Gopalan, F. Van Middlesworth, W. R. Shieh, C. J. Sih, J. Am. Chem. Soc. 1983, 105, 5925-5926.
39. T. Sakai, K. Mori, Agric. Biol. Chem. 1986, 50, 177-183
40. T. Katsuki, M. Yamaguchi, Tetrahedron Lett. 1987, 28, 651-654
41. J. Ferreira, F. Simonelli, Tetrahedron 1990, 46, 6311-6318
42. A. Tai, N. Morimoto, M. Yoshikawa, K. Uehara, T. Sugimura, T. Kikukawa, Agric. Biol. Chem. 1990, 54, 1753-1762.
43. G. Cainelli, M. Contento, D. Giacomini, M. Panunzio, Tetrahedron Lett. 1985, 26, 937-940
44. D. J. Hart, D.-C. Hua, Tetrahedron Lett. 1985, 26, 5493-5496
45. D. Seebach, B. Seuring, H.-O. Kalinowski, W. Lubosch, B. Renger, Angew. Chem. 1977, 89, 270-271
46. G. E. Keck, D. F. Kachensky, E. J. Enholm, J. Org. Chem. 1984, 49, 1462-1464.
47. K. Mori, Z.-H. Qian, Bull. Soc. Chim. Fr. 1993, 130, 382-387
48. K. Mori, M. Ikunaka, Tetrahedron 1987, 43, 45-58.
49. S. Kamitori, A. Iguchi, A. Ohtaki, M. Yamada, K. Kita, J. Mol. Biol. 2005, 352, 551-558.
50. Y.-H. Choi, H.-J. Choi, D. Kim, K.-N. Uhm, H.-K. Kim, Appl. Microbiol. Biotechnol. 2010, 87, 185-193.
51. Y. Ni, J.-H. Xu, J. Mol. Catal. B: Enzym. 2002, 18, 233-241
52. W. Yang, J.-H. Xu, Y. Xie, Y. Xu, G. Zhao, G.-Q. Lin, Tetrahedron: Asymmetry 2006, 17, 1769-1774
53. Y. Xie, J.-H. Xu, W.-Y. Lu, G.-Q. Lin, Bioresour. Technol. 2009, 100, 2463-2468
54. L.-J. Wang, C.-X. Li, Y. Ni, J. Zhang, X. Liu, J.-H. Xu, Bioresour. Technol. 2011, 102, 7023-7028
55. Y. Ni, C.-X. Li, L.-J. Wang, J. Zhang, J.-H. Xu, Org. Biomol. Chem. 2011, 9, 5463-5468
56. N.-D. Shen, Y. Ni, H.-M. Ma, L.-j. Wang, C.-X. Li, G.-W. Zheng, J. Zhang, J.-H. Xu, Org. Lett. 2012, 14, 1982-1985.
57. N. W. Fadnavis, K. R. Radhika, Tetrahedron: Asymmetry 2004, 15, 3443-3447.
58. A. Wolfson, C. Dlugy, D. Tavor, J. Blumenfeld, Y. Shotland, Tetrahedron: Asymmetry 2006, 17, 2043-2045.
59. R. A. Friesner, J. L. Banks, R. B. Murphy, T. A. Halgren, J. J. Klicic, D. T. Mainz, M. P. Repasky, E. H. Knoll, M. Shelley, J. K. Perry, D. E. Shaw, P. Francis, P. S. Shenkin, J. Med. Chem. 2004, 47, 1739-1749
60. T. A. Halgren, R. B. Murphy, R. A. Friesner, H. S. Beard, L. L. Frye, W. T. Pollard, J. L. Banks, J. Med. Chem. 2004, 47, 1750-1759.
61. U. C. Oppermann, C. Filling, H. Jornvall, Chem.-Biol. Interact. 2001, 130-132, 699-705.
62. L. Schuler, X. Daura, W. Van Gunsteren, J. Comput. Chem. 2001, 22, 1205-1218.