Cofactor recycling mechanism in asymmetric biocatalytic reduction of carbonyl compounds mediated by yeast: Which is the efficient electron donor?

Chemistry - A European Journal

Volumn 9, Issue 15, 2003, Pages 3604-3610

  Zhang, Ben Li ^a   Pionnier, Sébastien ^a  

^a Centre National de la Recherche Scientifique   (France)

Author keywords

Cofactor regeneration; Enzyme catalysis; Hydrides; Isotopic labeling; Yeast

Indexed keywords

BIOCATALYSTS; ELECTRONS; GLUCOSE; OXIDATION; YEAST;

COFACTOR RECYCLING;

MICROORGANISMS;

ALCOHOL; CARBON; CARBONYL DERIVATIVE; GLUCOSE; HEXOSE PHOSPHATE; HYDROGEN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; WATER;

ARTICLE; BIOCATALYST; CATALYSIS; ELECTRON; ELECTRON TRANSPORT; GLYCOLYSIS; ISOTOPE LABELING; NONHUMAN; REACTION ANALYSIS; RECYCLING; REDUCTION; SYNTHESIS; YEAST;

BIOTRANSFORMATION; BUTYRIC ACIDS; CARBOHYDRATE METABOLISM; CARBOHYDRATES; CATALYSIS; ELECTRON TRANSPORT; ETHANOL; NAD; NADP; SACCHAROMYCES;

EID: 0042967675     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304761     Document Type: Article

References (32)

1. K. Faber, Biotransformations in Organic Chemistry 3rd ed., Springer, Berlin, 1997.
2. R. Csuk, B. I. Glänzer, Chem. Rev. 1991, 91, 49-97.
3. H. Simon, J. Bader, H. Günther, S. Neumann, J. Thanos, Angew. Chem. 1985, 97, 541-555; Angew. Chem. Int. Ed. Engl. 1985, 24, 539-553.
4. H. Simon, J. Bader, H. Günther, S. Neumann, J. Thanos, Angew. Chem. 1985, 97, 541-555; Angew. Chem. Int. Ed. Engl. 1985, 24, 539-553.
5. M. Bucciarelli, A. Forni, I. Moretti, T. Giovanni, Synthesis, 1983, 897-899.
6. W. E H. Sybesma, A. J. J. Straathof, J. A. Jongejan, J. T. Pronk, J. J. Heijnen, Biocatal Biotransform. 1998, 16, 95-134.
7. L. Y. Jayasinghe, D. Kodituwakku, A. J. Smallridge, M. A. Trewhella, Bull. Chem. Soc. Jpn. 1994, 67, 1528-1531.
8. I. Chin-Joe, A. J. J. Straathof, J. T. Pronk, J. A. Jongeja, J. J. Heijnen, Biotechnol. Bioeng. 2001, 275, 29-38.
9. M. Bertau, M. Bürli, Chimia, 2000, 54, 503-507.
10. F. H. Westheimer, H. F. Fisher, E. E. Conn, B. Vennesland, J. Am. Chem. Soc. 1951, 73, 2403.
11. G. J. Martin, M. L. Martin, Tetrahedron Lett. 1981, 2, 3525-3528.
12. M. L. Martin, G. J. Martin in NMR Basic Principles and Progress, Vol 23, (Eds.: P. Diehl, E. Fluck, H. Günther, R. Kosfeld, J. Seelig) Springer, Berlin, 1990, pp. 1-61.
13. G. J. Martin, B. L. Zhang, N. Naulet, M. L. Martin, J. Am. Chem. Soc. 1986, 108, 5116-5122.
14. B. L. Zhang, Yunianta; M. L. Martin, J. Biol. Chem. 1995, 270, 16023-16029.
15. B. L. Zhang, S. Buddrus, M. L. Martin, Bioorg. Chem. 2000, 28, 1-15.
16. S. Pionnier, B. L. Zhang, Anal. Biochem. 2002, 307, 138-146.
17. B. L. Zhang, I. Billault, X. B. Li, F. Mabon, G. Remaud, M. L. Martin, J. Agric. Food Chem. 2002, 50, 1574-1580.
18. B. L. Zhang, S. Pionnier, Nukleonika, 2002, 47, S29-S31.
19. S. Pionnier, R. Robins, B. L. Zhang, J. Agric. Food Chem. 2003, 51, 2076-2082.
20. S. V. Rieder, I. A. Rose, J. Biol. Chem. 1959, 234, 1007-1010.
21. C. Rabiller, M. Mesbahi, M. L. Martin, Chirality 1990, 2, 85-89.
22. F. A. Loewus, F. H. Westheimer, B. Vennesland, J. Am. Chem. Soc. 1953, 75, 5018-5023;
23. H. Simon, M. Kellner, H. Günther, Angew. Chem. 1968, 80, 915; Angew. Chem. Int. Ed. Engl. 1968, 7, 892.
24. H. Simon, M. Kellner, H. Günther, Angew. Chem. 1968, 80, 915; Angew. Chem. Int. Ed. Engl. 1968, 7, 892.
25. M. Kataoka, Y. Nomura, S. Shimizu, H. Yamada, Biosci. Biotech. Biochem. 1992, 56, 820-821.
26. J. Ehrler, F. Giovannini, B. Lamatsch, D. Seebach, Chimia, 1986, 40, 172-173.
27. T. Kometani, Y. Morita, H. Furui, H. Yoshii, R. Matsuno, J. Ferment. Bioeng. 1994, 77, 13-16
28. D. Seebach, S. Roggo, T. Maetzke, H. Braunschweiger, J. Cercus, M. Krieger, Helv. Chim. Acta 1987, 70, 1605-1615.
29. M. Zhang, H. A. Melouk, K. Chenault, Z. El Rassi, J. Agric. Food Chem. 2001, 49, 5265-5269.
30. C. Vallet, R. Said, C. Rabiller, M. L. Martin, Bioorg. Chem. 1996, 24, 319-330.
31. L. F. Fieser, K. L. Williamson, Organic Experiments 6th ed., Heath, Lexington, 1987, pp. 338-340.
32. Y. L. Martin, J. Magn. Reson. 1994, 111, 1-10.