Reduction of C[dbnd]O to CHOH Using Enzymes and Microorganisms

Comprehensive Organic Synthesis

Volumn , Issue , 2014, Pages 317-327

  Truppo, M ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Alcohol; Alcohol dehydrogenase; Chiral; Cofactor recycling; Enzyme; Ketone; Ketoreductase; Reduction; Whole cell

Indexed keywords

EID: 84937124576     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-08-097742-3.00809-0     Document Type: Chapter

References (60)

1. Nakamura K. Tetrahedron Asymmetry 2003, 14:2659-2681.
2. Straathof A.J., Panke S., Schmid A. Curr. Opin. Biotechnol. 2002, 13:548-556.
3. Nakamura K., Matsuda T. Reduction of Ketones. Enzyme Catalysis in Organic Synthesis 2002, 991-1061. Wiley-VCH Verlag GmbH, Weinheim. K. Drauz, H. Waldmann (Eds.).
4. Walsh C. Enzymatic Reaction Mechanisms 1979, W.H. Freeman and Company, New York.
5. Homann M.J., Vail R.B., Previte E., et al. Tetrahedron 2004, 60:789-797.
6. Dumas J.B. Ann. Chim. Phys. 1874, 5:8-10.
7. Crocq V., Masson C., Winter J., et al. Org. Process Res. Dev. 1997, 1:2-13.
8. Ema T., Moriya H., Kofukuda T., et al. J. Org. Chem. 2001, 66:8682-8684.
9. Pollard D.J., Telari K., Lane J., et al. Biotechnol. Bioengineer. 2006, 93:674-686.
10. Galibert F., Alexandraki D., Baur A., et al. EMBO J. 1996, 15:2031-2049.
11. Zagulski M., Herbert C.J., Rytka J. Acta Biochim. Polonica 1998, 45:627-643.
12. Oppermann U.C.T., Maser E. Toxicology 2000, 144:71-81.
13. Rodriguez S., Kayser M.M., Stewart J.D. J. Am. Chem. Soc. 2001, 123:1547-1555.
14. Shieh W.R., Gopalan A.S., Sih C.J. J. Am. Chem. Soc. 1985, 107:2993-2994.
15. Kaluzna I.A., Rozzell J.D., Kambourakis S. Tetrahedron Asymmetry 2005, 16:3682-3689.
16. Huisman G.W., Liang J., Krebber A. Curr. Opin. Chem. Biol. 2010, 14:122-129.
17. Hummel W. Trends in Biotechnol. 1999, 17:487-492.
18. Pollard D., Truppo M., Pollard J., Chen C.Y., Moore J. Tetrahedron Asymmetry 2006, 17:554-559.
19. Moore J.C., Pollard D.J., Kosjek B., Devine P.N. Acc. Chem. Res. 2007, 40:1412-1419.
20. De Wildeman S.M.A., Sonke T., Schoemaker H.E., May O. Acc. Chem. Res. 2007, 40:1260-1266.
21. Bommarius A.S., Drauz K., Hummel W., Kula M.R., Wandrey C. Biocatalysis 1994, 10:37-47.
22. Wichmann R., Wandrey C., Buckmann A.F., Kula M.R. Biotechnol. Bioengineer. 2000, 67:791-804.
23. Seelbach K., Riebel B., Hummel W., et al. Tetrahedron Lett. 1996, 37:1377-1380.
24. Vrtis J.M., White A.K., Metcalf W.W., van der Donk W.A. Angew. Chem. Int. Ed. 2002, 41:3257-3259.
25. Bradshaw C.W., Hummel W., Wong C.H. J. Org. Chem. 1992, 57:1532-1536.
26. Nakamura K., Matsuda T. J. Org. Chem. 1998, 63:8957-8964.
27. Gooding O.W., Voladri R., Bautista A., et al. Org. Process Res. Dev. 2010, 14:119-126.
28. Gupta, A.; Zimmer, A.; Bobkova, M. 2-Butanol Production Method, I.B. World Intellectual Prop. 2005/108593 A1, 2005.
29. Schroer K., Lutz S. Org. Process Res. Dev. 2009, 13:1202-1205.
30. Ma S.K., Gruber J., Davis C., et al. Green Chem. 2010, 12:81-86.
31. Goldberg S., Guo Z.W., Chen S., Goswami A., Patel R.N. Enzyme Microb. Tech. 2008, 43:544-549.
32. Guo Z.W., Chen Y.J., Goswami A., Hanson R.L., Patel R.N. Tetrahedron Asymmetry 2006, 17:1589-1602.
33. Wu X.R., Wang L.L., Wang S.Z., Chen Y.J. Amino Acids 2010, 39:305-308.
34. Campopiano, O.; Mundorff, E.; Borup, B.; Voladri, R. Ketoreductase Polypeptides for the Production of Azetidinone, I.B. World Intellectual Prop. 2009/046153, 2009.
35. Grau B.T., Devine P.N., DiMichele L.N., Kosjek B. Org. Lett. 2007, 9:4951-4954.
36. Kataoka M., Nakamura Y., Urano N., et al. Lett. Appl. Microbiol. 2006, 43:430-435.
37. Truppo M.D., Pollard D., Devine P. Org. Lett. 2007, 9:335-338.
38. Schmidt F., Stemmler R.T., Rudolph J., Bolm C. Chem. Soc. Rev. 2006, 35:454-470.
39. Devalia J.L., De Vos C., Hannotte F., Baltes E. Allergy 2001, 56:50-57.
40. Corey E.J., Helal C.J. Tetrahedron Lett. 1996, 37:4837-4840.
41. Blaser H.U., Malan C., Pugin B., et al. Adv. Synth. Catal. 2003, 345:103-151.
42. Corey E.J., Helal C.J. Angew. Chem. Int. Ed. 1998, 37:1987-2012.
43. O'Shea P.D., Chen C.Y., Chen W.R., et al. J. Org. Chem. 2005, 70:3021-3030.
44. Brown E., Penfornis A., Bayma J., Touet J. Tetrahedron Asymmetry 1991, 2:339-342.
45. Brown E., Leze A., Touet J. Tetrahedron Asymmetry 1992, 3:841-844.
46. Shieh W.C., Cantrell W.R., Carlson J.A. Tetrahedron Lett. 1995, 36:3797-3800.
47. Corey E.J., Helal C.J. Tetrahedron Lett. 1996, 37:5675-5678.
48. Ohkuma T., Koizumi M., Ikehira H., Yokozawa T., Noyori R. Org. Lett. 2000, 2:659-662.
49. Corey E.J., Helal C.J. Tetrahedron Lett. 1995, 36:9153-9156.
50. Zhao G., Li X.G., Wang X.R. Tetrahedron Asymmetry 2001, 12:399-403.
51. Homann, M. J.; Previte E. Stereoselective Microbial Reduction of 5-Fluorophenyl-5-Oxopentanoic Acid And A Phenyloxazolidinone Condensation Product Thereof. US 5,618,707; 1997.
52. Mundorff, E.; De Vries, E. Ketoreductase Polypeptides for the Stereoselective Production of (4S)-3[(5S)-5(4-Fluorophenyl)-5-Hydroxypentanoyl]-4-Phenyl-1,3-Oxazolidin-2-One, I.B. World Intellectual Property 2010/025085; 2010.
53. Liang J., Lalonde J., Borup B., et al. Org. Process Res. Dev. 2010, 14:193-198.
54. Liang J., Mundorff E., Voladri R., et al. Org. Process Res. Dev. 2010, 14:188-192.
55. Liang, J.; Jenne, S. J.; Mundorff, E.; Voladri, R. L.; Huisman, J. G. Improved Ketoreductase Polypeptides for the Stereoselective Production of (R)-3-Hydroxythiolane, I.B. World Intellectual Prop. 2009/029554; 2009.
56. Kosjek B., Nti-Gyabaah J., Telari K., Dunne L., Moore J.C. Org. Process Res. Dev. 2008, 12:584-588.
57. Kosjek B., Tellers D.M., Biba M., Farr R., Moore J.C. Tetrahedron Asymmetry 2006, 17:2798-2803.
58. Goldberg K., Schroer K., Lutz S., Liese A. Appl. Microbiol. Biotechnol. 2007, 76:237-248.
59. Goldberg K., Schroer K., Lutz S., Liese A. Appl. Microbiol. Biotechnol. 2007, 76:249-255.
60. Matsuda T., Yamanaka R., Nakamura K. Tetrahedron Asymmetry 2009, 20:513-557.