Towards practical biocatalytic Baeyer-Villiger reactions: Applying a thermostable enzyme in the gram-scale synthesis of optically-active lactones in a two-liquid-phase system

Beilstein Journal of Organic Chemistry

Volumn 1, Issue , 2005, Pages

  Schulz, Frank ^a   Leca, François ^a   Hollmann, Frank ^a   Reetz, Manfred T ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845706042     PISSN: 18605397     EISSN: 18605397     Source Type: Journal    
DOI: 10.1186/1860-5397-1-10     Document Type: Article

References (60)

1. Baeyer A, Villiger V: Ber Dtsch Chem Ges 1899, 32:3625-3633.
2. ten Brink G-J, Arends IWCE, Sheldon RA: Chem Rev 2004, 104:4105-4123.
3. Bolm C, Luong TKK, Beckmann O: Asymmetric Oxidation Reactions Edited by: Katsuki T. Oxford: University Press; 2001:147.
4. Krow GR: Org React (NY) 1993, 43:251-798.
5. Renz M, Meunier B: Eur J Org Chem 1999:737-750.
6. Strukul G: Angew Chem Int Ed 1998, 37:1198-1209.
7. Sheng D, Ballou DP, Massey V: Biochemistry 2001, 40:11156-11167.
8. Turfitt GE: Biochem J 1948, 42:376-383.
9. Schwab JM, Li WB, Thomas LP: J Am Chem Soc 1983, 105:4800-4808.
10. Donoghue NA, Norris DB, Trudgill PW: Eur J Biochem 1976, 63:175-192.
11. Walsh CT, Cheng Y-CJ: Angew Chem Int Ed Engl 1988, 27:333-343.
12. Bolm C, Palazzi C, Beckmann O: Metal-Catalyzed Baeyer-Villiger Reactions. In Transition Metals For Organic Chemistry: Building Blocks and Fine Chemicals Volume 2. 2nd edition. Edited by: Beller M, Bolm C. Weinheim: Wiley-VCH; 2004:267-274.
13. Murahashi S-I, Ono S, Imada Y: Angew Chem Int Ed 2002, 41:2366-2368.
14. Murahashi S-I, Oda T, Masui Y: J Am Chem Soc 1989, 111:5002-5003.
15. Imada Y, Iida H, Murahashi S-I, Naota T: Angew Chem Int Ed 2005, 44:1704-1706.
16. Stewart JD: Curr Org Chem 1998, 2:195-216.
17. Doig SD, O'Sullivan LM, Patel S, Ward JM, Woodley JM: Enzyme Microb Technol 2001, 28:265-274.
18. Flitsch S, Grogan G: Baeyer-Villiger Oxidations. In Enzyme Catalysis in Organic Chemistry Volume 3. Edited by: Drauz K, Waldmann H. Weinheim: Wiley-VCH; 2002:1202-1245.
19. Kamerbeek NM, Janssen DB, van Berkel WJH, Fraaije MW: Adv Synth Catal 2003, 345:667-678.
20. Mihovilovic MD, Rudroff F, Grötzl B: Curr Org Chem 2004, 8:1057-1069.
21. Stewart JD, Reed KW, Martinez CA, Zhu J, Chen G, Kayser MM: J Am Chem Soc 1998, 120:3541-3548.
22. Kyte BG, Rouvière P, Cheng Q, Stewart JD: J Org Chem 2004, 69:12-17.
23. Taschner MJ, Black DJ: J Am Chem Soc 1988, 110:6892-6893.
24. Stewart JD, Reed KW, Zhu J, Chen G, Kayser MM: J Org Chem 1996, 61:7652-7653.
25. Alphand V, Furstoss R, Pedragosa-Moreau S, Roberts SM, Willetts AJ: J Chem Soc, Perkin Trans I 1996:1867-1872.
26. Mihovilovic MD, Müller B, Schulze A, Stanetty P, Kayser MM: Eur J Org Chem 2003:2243-2249.
27. Duetz WA, van Beilen JB, Witholt B: Curr Opin Biotechnol 2001, 12:419-425.
28. Bühler B, Schmid A: J Biotechnol 2004, 113:183-210.
29. Li Z, van Beilen JB, Duetz WA, Schmid A, de Raadt A, Griengl H, Witholt B: Curr Opin Chem Biol 2002, 6:136-144.
30. Mihovilovic MD, Müller B, Stanetty P: Eur J Org Chem 2002:3711-3730.
31. Simpson HD, Alphand V, Furstoss R: J Mol Catal B: Enzym 2001, 16:101-108. for a case of an industrially viable biocatalytic Baeyer-Villiger-Oxidation.
32. Hilker I, Alphand V, Wohlgemuth R, Furstoss R: Adv Synth Catal 2004, 346:203-214. for a case of an industrially viable biocatalytic Baeyer-Villiger-Oxidation
33. Ghisla S, Massey V: Eur J Biochem 1989, 181:1-17.
34. Vilker VL, Reipa V, Mayhew MP, Holden MJ: J Am Oil Chem Soc 1999, 76:1283-1289.
35. Palfey A, Massey V: Flavin-dependent enzymes. In Comprehensive Biological Catalysis Volume 3. Edited by: Sinnott M. San Diego: Academic Press; 1998:83-154.
36. Reetz MT: Proc Natl Acad Sci USA 2004, 101:5716-5722.
37. Reetz MT, Bocola M, Carballeira JD, Zha D, Vogel A: Angew Chem Int Ed 2005, 44:4192-4196.
38. Directed Enzyme Evolution: Screening and Selection Methods Edited by: Arnold FH, Georgiou G. Totowa: Humana Press; 2003. Methods in Molecular Biology, vol 230.
39. Reetz MT, Brunner B, Schneider T, Schulz F, Clouthier CM, Kayser MM: Angew Chem Int Ed 2004, 43:4075-4078.
40. Reetz MT, Daligault F, Brunner B, Hinrichs H, Deege A: Angew Chem Int Ed 2004, 43:4078-4081.
41. Zambianchi F, Pasta P, Carrea G, Colonna S, Gaggero N, Woodley JM: Biotechnol Bioeng 2002, 78:489-496.
42. Walton AZ, Stewart JD: Biotechnol Prog 2004, 20:403-411.
43. Malito E, Alfieri A, Fraaije MW, Mattevi A: Proc Natl Acad Sci U S A 2004, 101:13157-13162.
44. Fraaije MW, Wu J, Heuts DPHM, van Hellemond EW, Spelberg JHL, Janssen DB: Appl Microbiol Biotechnol 2005, 66:393-400.
45. Bocola M, Schulz F, Leca F, Vogel A, Fraaije MW, Reetz MT: Adv Synth Catal 2005, 347:979-986.
46. Alphand V, Archelas A, Furstoss R: Tetrahedron Lett 1989, 30:3663-3664.
47. Laane C, Boeren S, Vos K, Veeger C: Biotechnol Bioeng 1987, 30:81-87.
48. Liese A: Adv Biochem Eng/Biotechnol 2005, 92:197-224.
49. Wichmann R, Vasic-Racki D: Adv Biochem Eng/Biotechnol 2005, 92:225-260.
50. van der Donk WA, Zhao H: Curr Opin Biotechnol 2003, 14:421-426.
51. Burdette DS, Tchernajencko V, Zeikus JG: Enzyme Microb Technol 2000, 27:11-18.
52. Zheng C, Pham VT, Phillips RS: Bioorg Med Chem Lett 1992, 2:619-622.
53. Heiss C, Laivenieks M, Zeikus JG, Phillips RS: Bioorg Med Chem 2001, 9:1659-1666.
54. Vieille C, Zeikus GJ: Microbiol Mol Biol Rev 2001, 65:1-43.
55. Tripp AE, Burdette DS, Zeikus JG, Phillips RS: J Am Chem Soc 1998, 120:5137-5141.
56. Burdette DS, Vieille C, Zeikus JG: Biochem J 1996, 316:115-122.
57. Hofstetter K, Lutz J, Lang I, Witholt B, Schmid A: Angew Chem Int Ed 2004, 43:2163-2166.
58. Villela Filho M, Stillger T, Müller M, Liese A, Wandrey C: Angew Chem Int Ed 2003, 42:2993-2996.
59. Chenault HK, Whitesides GM: Appl Biochem Biotechnol 1987, 14:147-197.
60. Willetts AJ, Knowles CJ, Levitt MS, Roberts SM, Sandey H, Shipston NF: J Chem Soc Perkin Trans 1 1991:1608-1610.