Coupling of the electroenzymatic reduction of NAD+ with a synthesis reaction

Enzyme and Microbial Technology

Volumn 18, Issue 1, 1996, Pages 72-79

  Cantet, Jean ^a   Bergel, Alain ^a   Comtat, Maurice ^a  

^a LABORATOIRE DE GÉNIE CHIMIQUE   (France)

Author keywords

Batch reactor; Bioelectrochemistry; Coenzyme regeneration; Hydrogenase; NAD

Indexed keywords

2 OXOGLUTARIC ACID; GLUTAMATE DEHYDROGENASE; GLUTAMIC ACID; HYDROGEN DEHYDROGENASE; NICOTINAMIDE ADENINE DINUCLEOTIDE; PYRIDINE;

ARTICLE; BIOREACTOR; BIOSYNTHESIS; COENZYME; ELECTROCHEMISTRY; ENZYME STABILITY; NONHUMAN; REDUCTION; WAUTERSIA EUTROPHA;

ALCALIGENES; WAUTERSIA EUTROPHA;

EID: 0030021337     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/0141-0229(96)00059-2     Document Type: Article

References (34)

1. Lee, L. G., and Whitesides, G. M. Enzyme-catalyzed organic synthesis: A comparison of strategies for in situ regeneration of NADH. J. Am. Chem. Soc. 1985, 107, 6999-7008
2. Chenault, H. K., and Whitesides, G. M. Regeneration of nicotinamide cofactors for use in organic synthesis. Appl. Biochem. Biotechnol. 1987, 14, 147-190
3. Chenault, H. K., Simon, E. S., and Whitesides, G. M. Cofactor regeneration for enzyme-catalysed synthesis. Biotechnol. Gen. Eng. Rev. 1988, 6, 221-270
4. Jones, J. B., Sneddon, D. W., Higgins, W., and Lewis, A. J. Preparative-scale reductions of cyclic ketone and aldehyde substrates of horse liver alcohol dehydrogenase with in situ sodium dithionite recycling of catalytic amounts of NAD. J. Chem. Soc. Chem. Commun., 1972, 856-857
5. Vandecasteele, J.-P. and Lemal, J. Synthèse Réductive de la L-carnitine par voie enzymatique avec régénération du NADH utilisé. Bull. Soc. Chim. 1980, II-101-II-103
6. 2 semiconductors: Applications in enzymatic synthesis. J. Mol. Catal. 1988, 47, 21-32
7. Shaked, Z., Barber, J. J., and Whitesides, G. M. A combined electrochemical-enzymatic method for in situ regeneration of NADH based on cathodic reduction of cyclic disulfides. J. Org. Chem. 1981, 46, 4100-4101
8. Di Cosimo, R., Wong, C. H., Daniels, L., and Whitesides, G. M. Enzyme-catalyzed organic synthesis: Electrochemical regeneration of NAD(P)H from NAD(P) using methyl viologen and flavoenzymes. J. Org. Chem. 1981, 46, 4622-4623
9. Kise, S. and Hayoshida, M. Two-phase system membrane reactor with cofactor recycling. J. Biotechnol. 1990, 14, 221-228
10. Wienkamp, R. and Steckhan, E. Indirect electrochemical regeneration of NADH by a bipyridinerhodium (I) complex as electron-transfer agent. Angew. Chem. Int. Ed. 1982, 21, 782-783
11. Shaked, Z. and Whitesides, G. M. Enzyme-catalyzed organic synthesis: NADH regeneration by using formate dehydrogenase. J. Am. Chem. Soc. 1980, 102, 7104-7105
12. Carrea, G., Riva, S., Bovara, R., and Pasta, P. Enzymatic oxidoreduction of steroids in two-phase systems: Effects of organic solvents on enzyme kinetics and evaluation of the performance of different reactors. Enzyme Microb. Technol. 1988, 10, 333-340
13. Wandrey, C. and Bossov, B. Continuous cofactor regeneration. In: Int. Conf. Chem. Biotechnol. Biol. Act. Nat. Proc. 3rd, 1987, 1, 195-214
14. Hummel, W., Schütte, H., Schmidt, E., Wandrey, C., and Kula, M.-R. L-Phenylalanine dehydrogenase from Brevibacterium sp. for production of L-phenylalanine by reductive animation of phenylpyruvate. Appl. Microbiol. Biotechnol. 1987, 25, 175-185
15. Kula, M. R. and Wandrey, C. Continuous enzymatic transformation in an enzyme-membrane reactor with simultaneous NADH regeneration. Methods Enzymol. 1987, 136, 9-21
16. Wong, C. H., Drueckhammer, D. G., and Sweers, H. M. Enzymatic vs. fermentive synthesis: Thermostable glucose dehydrogenase catalyzed regeneration of NADH(P)H for use in enzymatic synthesis. J. Am. Chem. Soc. 1985, 107, 4028-4031
17. Wong, C. H. and Whitesides, G. M. Enzyme-catalyzed organic synthesis: NAD(P)H cofactor regeneration by using glucose 6-phosphate and the glucose-6-phosphate dehydrogenase from Leuconostoc mesenteroides. J. Am. Chem. Soc. 1981, 103, 4890-4899
18. Wong, C. H. and Whitesides, G. M. Enzyme-catalyzed organic synthesis: NAD(P)H cofactor regeneration using ethanol-alcohol dehydrogenase-aldehyde dehydrogenase and methanol-alcohol dehydrogenase-aldehyde dehydrogenase-formate dehydrogenase. J. Org. Chem. 1982, 47, 2816-2818
19. Nakamura, A., Minami, H., Urabe, I., and Okada, H. Properties of glucose-dehydrogenase-poly(ethylene glycol)-NAD conjugate as an NADH-regeneration unit in enzyme reactors. J. Ferment. Technol. 1988, 66, 267-272
20. Persson, M., Manson, M.-O., Bülow, L., and Mosbach, K. Continuous regeneration of NAD(H) covalently bound to a cysteine genetically engineered into glucose dehydrogenase. Biotechnol. 1991, 9, 280-284
21. Miyawaki, O., Nakamura, K., and Yano, T. Experimental investigation of continuous NAD recycling by conjugated enzymes immobilized in ultrafiltration hollow fiber. J. Chem. Eng. Jap. 1982, 15, 224-228
22. Fujii, T., Miyawaki, O., and Yano, T. Modelling of hollow-fiber capillary reactor for the production of L-alanine with coenzyme regeneration. Biotechnol. Bioeng. 1991, 38, 1166-1172
23. Grundwald, J., Wirg, B. Scollar, M. P., and Klibanov, A. M. Asymmetric oxidoreductions catalyzed by alcohol dehydrogenase in organic solvents. J. Am. Chem. Soc. 1986, 108, 6732-6734
24. Danielson, B., Winqvist, F., Malpote, J.-Y., and Mosbach, K. Regeneration of NADH with immobilized systems of alanine dehydrogenase and hydrogen dehydrogenase. Biotechnol. Lett. 1982, 4, 673-678
25. Otsuka, K., Aono, S., Okura, I., and Hasumi, F. Regeneration of NADH and ketone hydrogenation by hydrogen with the combination of hydrogenase and alcohol dehydrogenase. J. Mol. Catal. 1989, 51, 35-39
26. Takeuchi, M., Okura, I., and Hasumi, F. Regeneration of NADH and hydrogenation of dihydroyacetone by hydrogen with the combination of hydrogenase and glycerol dehydrogenase. J. Mol. Catal. 1991, 68, L21-L23
27. Wong, C. H., Daniels, L., Orme-Johnson, W. H., and Whitesides, G. M. Enzyme-catalyzed organic synthesis: NAD(P)H regeneration using dihydrogen and the hydrogenase from Methanobacterium thermoautotrophicum. J. Am. Chem. Soc. 1981, 103, 6227-6228
28. Llopart, S. Régénération enzymatique du cofacteur NADH. Application à la synthèse de la L-carnitine. Thèse Docteur-Ingénieur (Ph.D. thesis), Univ. Paul Sabatier, Toulouse, France, 1986
29. Klibanov, A. M. and Puglisi, A. V. The regeneration of coenzymes using immobilized hydrogenase. Biotechnol. Lett. 1980, 2, 445-450
30. Durliat, H., Comtat M., and Séris, J.-L. Procédé de régénération électrochimique de cofacteurs pyridiniques. French patent no. 88 11933, 1988
31. +. J. Mol. Catal. 1992, 73, 371-380
32. + reduction. Bioelectrochem. Bioenerg. 1992, 27, 475-486
33. Payen, B., Segui, M., Monsan, P., Schneider, K., Friedrich, C., and Schlegel. H. G. Use of cytoplasmic hydrogenase from Alcaligenes eutrophus for NADH regeneration. Biotechnol. Lett. 1983, 5, 463-468
34. Barman, T. E. Enzyme H and book. Vol. 1. Springer-Verlag, New York, 1985, 170-171