Escherichia coli/ADH-A: An all-inclusive catalyst for the selective biooxidation and deracemisation of secondary alcohols

ChemCatChem

Volumn 5, Issue 12, 2013, Pages 3875-3881

  Paul, Caroline E ^a   Lavandera, Iván ^a   Gotor Fernández, Vicente ^a   Kroutil, Wolfgang ^b   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

^b UNIVERSITY OF GRAZ   (Austria)

Author keywords

alcohols; cofactors; deracemization; enzymes; oxidation

Indexed keywords

ALCOHOL DEHYDROGENASE; COFACTORS; DE-RACEMIZATION; ENANTIOPURE ALCOHOLS; ESCHERICHIA COLI CELLS; GLUCOSE DEHYDROGENASE; LACTOBACILLUS BREVIS; NICOTINAMIDE ADENINE DINUCLEOTIDES;

ALCOHOLS; AMIDES; CELLS; CYTOLOGY; ENZYMES; ESCHERICHIA COLI; ETHANOL; KETONES; SUBSTRATES;

OXIDATION;

EID: 84889780415     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201300409     Document Type: Article

References (73)

1. F. Hollmann, K. Bühler, B. Bühler, in Enzyme Catalysis in Organic Synthesis (Eds.:, K. Drauz, H. Gröger, O. May,), Wiley-VCH, Weinheim, 2012, pp. 1325-1438
2. D. Romano, R. Villa, F. Molinari, ChemCatChem 2012, 4, 739-749
3. F. Hollmann, I. W. C. E. Arends, K. Buehler, A. Schallmey, B. Bühler, Green Chem. 2011, 13, 226-265
4. N. J. Turner, Chem. Rev. 2011, 111, 4073-4087
5. Modern Biooxidation. Enzymes, Reactions and Applications (Eds.:, R. D. Schmid, V. B. Urlacher,), Wiley-VCH, Weinheim, 2007
6. W. Kroutil, H. Mang, K. Edegger, K. Faber, Adv. Synth. Catal. 2004, 346, 125-142.
7. C. Rodríguez, I. Lavandera, V. Gotor, Curr. Org. Chem. 2012, 16, 2525-2541
8. M. Hall, A. S. Bommarius, Chem. Rev. 2011, 111, 4088-4110
9. A. Weckbecker, H. Gröger, W. Hummel, Adv. Biochem. Eng. Biotechnol. 2010, 120, 195-242
10. F. Hollmann, I. W. C. E. Arends, K. Buehler, ChemCatChem 2010, 2, 762-782
11. W. A. van der Donk, H. Zhao, Curr. Opin. Biotechnol. 2003, 14, 421-426
12. M. D. Leonida, Curr. Med. Chem. 2001, 8, 345-369.
13. G. Brown, D. Mangan, I. Miskelly, T. S. Moody, Org. Process Res. Dev. 2011, 15, 1036-1039
14. N. A. Magnus, D. S. Coffey, A. C. DeBaillie, C. D. Jones, I. A. Kaluzna, S. Kambourakis, Y. J. Pu, L. Wang, J. P. Wepsiec, Org. Process Res. Dev. 2011, 15, 1377-1381
15. J. Liang, E. Mundorff, R. Voladri, S. Jenne, L. Gilson, A. Conway, A. Krebber, J. Wong, G. Huisman, S. Truesdell, J. Lalonde, Org. Process Res. Dev. 2010, 14, 188-192
16. J. Liang, J. Lalonde, B. Borup, V. Mitchell, E. Mundorff, N. Trinh, D. A. Kochrekar, R. N. Cherat, G. G. Pai, Org. Process Res. Dev. 2010, 14, 193-198.
17. H. K. Chenault, G. M. Whitesides, Bioorg. Chem. 1989, 17, 400-409.
18. H. K. Chenault, G. M. Whitesides, Appl. Biochem. Biotechnol. 1987, 14, 147-197.
19. T. Orbegozo, J. G. de Vries, W. Kroutil, Eur. J. Org. Chem. 2010, 3445-3448
20. T. Orbegozo, I. Lavandera, W. M. F. Fabian, B. Mautner, J. G. de Vries, W. Kroutil, Tetrahedron 2009, 65, 6805-6809
21. M. M. Musa, K. I. Ziegelmann-Fjeld, C. Vieille, J. G. Zeikus, R. S. Phillips, J. Org. Chem. 2007, 72, 30-34
22. K. Edegger, H. Mang, K. Faber, J. Gross, W. Kroutil, J. Mol. Catal. A-Chem. 2006, 251, 66-70.
23. X. Wu, H. Kobori, I. Orita, C. Zhang, T. Imanaka, X.-H. Xing, T. Fukui, Biotechnol. Bioeng. 2012, 109, 53-62
24. L. Wang, H. Zhang, C.-B. Ching, Y. Chen, R. Jiang, Appl. Microbiol. Biotechnol. 2012, 94, 1233-1241
25. J. Rocha-Martín, D. Vega, J. M. Bolivar, C. A. Godoy, A. Hidalgo, J. Berenguer, J. M. Guisán, F. Lõpez-Gallego, BMC Biotechnol. 2011, 11, 101
26. J.-I. Hirano, K. Miyamoto, H. Ohta, Tetrahedron Lett. 2008, 49, 1217-1219
27. C. V. Voss, C. C. Gruber, K. Faber, T. Knaus, P. Macheroux, W. Kroutil, J. Am. Chem. Soc. 2008, 130, 13969-13972
28. P. Ödman, W. B. Wellborn, A. S. Bommarius, Tetrahedron: Asymmetry 2004, 15, 2933-2937
29. W. Hummel, M. Kuzu, B. Geueke, Org. Lett. 2003, 5, 3649-3650
30. B. Geueke, B. Riebel, W. Hummel, Enzyme Microb. Technol. 2003, 32, 205-211
31. B. R. Riebel, P. R. Gibbs, W. B. Wellborn, A. S. Bommarius, Adv. Synth. Catal. 2003, 345, 707-712.
32. Z. Xiao, C. Lv, C. Gao, J. Qin, C. Ma, Z. Liu, P. Liu, L. Li, P. Xu, PLoS One 2010, 5, e 8860.
33. J. H. Schrittwieser, J. Sattler, V. Resch, F. G. Mutti, W. Kroutil, Curr. Opin. Chem. Biol. 2011, 15, 249-256
34. E. Ricca, B. Brucher, J. H. Schrittwieser, Adv. Synth. Catal. 2011, 353, 2239-2262
35. N. J. Turner, Curr. Opin. Chem. Biol. 2010, 14, 115-121
36. C. C. Gruber, I. Lavandera, K. Faber, W. Kroutil, Adv. Synth. Catal. 2006, 348, 1789-1805.
37. C. V. Voss, C. C. Gruber, W. Kroutil, Synlett 2010, 991-998.
38. D. Monti, E. E. Ferrandi, I. Zanellato, L. Hua, F. Polentini, G. Carrea, S. Riva, Adv. Synth. Catal. 2009, 351, 1303-1311.
39. Y.-L. Li, J.-H. Xu, Y. Xu, J. Mol. Catal. B-Enzym. 2010, 64, 48-52
40. C. V. Voss, C. C. Gruber, W. Kroutil, Angew. Chem. 2008, 120, 753-757
41. Angew. Chem. Int. Ed. 2008, 47, 741-745.
42. K. Edegger, C. C. Gruber, T. M. Poessl, S. R. Wallner, I. Lavandera, K. Faber, F. Niehaus, J. Eck, R. Oehrlein, A. Hafner, W. Kroutil, Chem. Commun. 2006, 2402-2404
43. W. Stampfer, B. Kosjek, C. Moitzi, W. Kroutil, K. Faber, Angew. Chem. 2002, 114, 1056-1059
44. Angew. Chem. Int. Ed. 2002, 41, 1014-1017.
45. S. Leuchs, L. Greiner, Chem. Biochem. Eng. Q. 2011, 25, 267-281
46. M. Wolberg, W. Hummel, C. Wandrey, M. Müller, Angew. Chem. 2000, 112, 4476-4478
47. Angew. Chem. Int. Ed. 2000, 39, 4306-4308.
48. A. Cuetos, A. Rioz-Martínez, F. R. Bisogno, B. Grischek, I. Lavandera, G. de Gonzalo, W. Kroutil, V. Gotor, Adv. Synth. Catal. 2012, 354, 1743-1749.
49. H. Erhardt, S. Steimle, V. Muders, T. Pohl, J. Walter, T. Friedrich, Biochim. Biophys. Acta Bioenerg. 2012, 1817, 863-871
50. D. Schneider, T. Pohl, J. Walter, K. Dörner, M. Kohlstädt, A. Berger, V. Spehr, T. Friedrich, Biochim. Biophys. Acta Bioenerg. 2008, 1777, 735-739
51. S. J. Kerscher, Biochim. Biophys. Acta Bioenerg. 2000, 1459, 274-283
52. T. Friedrich, Biochim. Biophys. Acta Bioenerg. 1998, 1364, 134-146.
53. R. K. Poole, Protein Rev. 2008, 9, 241-257
54. A. Bonamore, A. Boffi, IUBMB Life 2008, 60, 19-28
55. M. F. Anjum, N. Ioannidis, R. K. Poole, FEMS Microbiol. Lett. 1998, 166, 219-223
56. R. K. Poole, N. Ioannidis, Y. Orii, Microbiology 1996, 142, 1141-1148.
57. + that is needed for the citric acid cycle; see:, U. Brandt, Biochim. Biophys. Acta Bioenerg. 1998, 1364, 85-86. The direct transfer of NADH from malate dehydrogenase to complex I in E. coli has also been described; see, for instance
58. + via the respiratory chain; see
59. C. Burstein, H. Ounissi, M. D. Legoy, G. Gellf, D. Thomas, Appl. Biochem. Biotechnol. 1981, 6, 329-338.
60. J. W. Thomson, B. M. Shapiro, J. Biol. Chem. 1981, 256, 3077-3084.
61. This biocatalyst is NADP dependent and highly (S)-selective; see:, I. Lavandera, A. Kern, B. Ferreira-Silva, A. Glieder, S. de Wildeman, W. Kroutil, J. Org. Chem. 2008, 73, 6003-6005.
62. This (S)-selective ADH is highly NADP dependent; see, for instance:, I. Lavandera, A. Kern, V. Resch, B. Ferreira-Silva, A. Glieder, W. M. F. Fabian, S. de Wildeman, W. Kroutil, Org. Lett. 2008, 10, 2155-2158.
63. + and shows (S)-stereopreference; see:, C. Heiss, R. S. Phillips, J. Chem. Soc., Perkin Trans. 1 2000, 2821-2825.
64. +, see:, Z. Findrik, D. Vasic̈-Racki, S. Lütz, T. Daussmann, C. Wandrey, Biotechnol. Lett. 2005, 27, 1087-1095.
65. R. Lundquist, B. M. Olivera, J. Biol. Chem. 1971, 246, 1107-1116.
66. E. Chave, E. Adamowicz, C. Burstein, Appl. Biochem. Biotechnol. 1982, 7, 431-441.
67. F. R. Bisogno, E. García-Urdiales, H. Valdés, I. Lavandera, W. Kroutil, D. Suárez, V. Gotor, Chem. Eur. J. 2010, 16, 11012-11019.
68. C. V. Voss, C. C. Gruber, W. Kroutil, Tetrahedron: Asymmetry 2007, 18, 276-281.
69. B. Kosjek, W. Stampfer, R. van Deursen, K. Faber, W. Kroutil, Tetrahedron 2003, 59, 9517-9521.
70. K. Edegger, W. Stampfer, B. Seisser, K. Faber, S. F. Mayer, R. Oehrlein, A. Hafner, W. Kroutil, Eur. J. Org. Chem. 2006, 1904-1909.
71. Furthermore, glucose is far less expensive than G6P. Sigma-Aldrich in Spain (http://www.sigmaaldrich.com/spain.html accessed May 21, 2013) sells 1 kg of glucose (G8270) for €37.20 whereas 1 g of G6P (G7879) costs €75.20.
72. H. Ma, L. Yang, Y. Ni, J. Zhang, C.-X. Li, G.-W. Zheng, H. Yang, J.-H. Xu, Adv. Synth. Catal. 2012, 354, 1765-1772
73. 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.