Asymmetric reduction of acetophenone with calcium-alginate-entrapped baker's yeast in organic solvents

Biotechnology Progress

Volumn 14, Issue 4, 1998, Pages 588-593

  Griffin, Daniel R ^a   Yang, Fangxiao ^a   Carta, Giorgio ^a   Gainer, John L ^a  

^a University of Virginia   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYLETHANOL; ACETOPHENONE; CALCIUM ALGINATE; IMMOBILIZED CELL; ORGANIC SOLVENT; YEAST;

ALCOHOLS; BIOSYNTHESIS; CALCIUM COMPOUNDS; CATALYSIS; FERMENTATION; KETONES; ORGANIC SOLVENTS; PH EFFECTS; REDUCTION; SUBSTRATES;

ACETOPHENONE; CALCIUM ALGINATE;

YEAST;

EID: 0032127795     PISSN: 87567938     EISSN: None     Source Type: Journal    
DOI: 10.1021/bp9800586     Document Type: Article

References (29)

1. Hutt, A. J.; Tan S. C. Drug Chirality and its Clinical Significance. Drugs 1996, 52 (Suppl. 5), 1-11.
2. Burger, A. Understanding Medications: What the Label Doesn't Tell You; American Chemical Society: Washington, DC, 1995.
3. Margolin, A. L. Enzymes in the Synthesis of Chiral Drugs. Enzyme Microb. Technol. 1993, 15, 266-280.
4. Bhalerao, U. T.; Dasaradhi, L.; Muralikrishna, C.; Fadnavis,: N. W. A Novel Chemo-Enzymatic Enantiospecific Synthesis of (S)-Coriolic Acid Mediated via Immobilized Alcohol Dehydrogenase of Baker's Yeast. Tetrahedron Lett. 1993, 34, 2359-2360.
5. Santaniello, E.; Ferraboschi, P.; Grisenti, P. Lipase-Catalyzed Transesterification in Organic Solvents: Applications to the Preparation of Enantiomerically Pure Compounds. Enzyme Microb. Technol. 1993, 15, 367-382.
6. Zaks, A.; Klibanov, A. Enzyme-Catalyzed Processes in Organic Solvents. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 3192-3196.
7. Terradas, F.; Teston-Henry, M.; Fitzpatrick, P. A.; Klibanov, A. M. Marked Dependence of Enzyme Prochiral Selectivity on the Solvent J. Am. Chem. Soc. 1993, 115, 390-396.
8. Maurel, P. Relevance of Dielectric Constant and Solvent Hydrophobicity to the Organic Solvent Effect in Enzymology. J. Biol. Chem. 1978, 253, 1677-1683.
9. Parida, S.; Dordick, J. S. Substrate Structure and Solvent Hydrophobicity Control Lipase Catalysis and Enantioselectivity in Organic Media. J. Am. Chem. Soc. 1991, 113, 2253-2259.
10. Nikolova, P.; Ward, O. P. Whole Cell Biocatalysis in Nonconventional Media. J. Ind. Microbiol. 1993, 12, 76-86.
11. Nakamura, K.; Kondo, S.; Kawai, Y.; Ohno, A. Stereochemical Control in Microbial Reduction. XXI. Effect of Organic Solvents on Reduction of α-Keto Esters Mediated by Baker's Yeast. Bull. Chem. Soc. Jpn. 1993, 66, 2738-2743.
12. Nikolova, P.; Ward, O. P. Effect of Organic Solvent on Biotransformation of Benzaldehyde to Benzyl Alcohol by Free and Silicon-Alginate Entrapped Cells. Biotechnol. Tech. 1993, 7, 897-902.
13. Knox, T.; Clefee, K. R. Synthesis of Long-Chain Estersin a Loop Reactor System using a Fungal Bound Enzyme. Process Biochem. 1984, 188-192.
14. Yang, F.; Russell, A. J. Optimization of Baker's Yeast Alcohol Dehydrogenase Activity in an Organic Solvent. Biotechnol. Prog. 1993, 9, 234-241.
15. Bailey, J. E. and Ollis, D. F. Biochemical Engineering Fundamentals; 2nd ed.; McGraw-Hill Inc.: New York, 1986.
16. Kawakami, K.; Tsuruda, S.; Miyagi, K.; Immobilization of Microbial Cells in a Mixed Matrix of Silicone Polymer and Calcium Alginate Gel: Epoxidation of 1-Octene by Nocardia corallina B-276 in Organic Media. Biotechnol. Prog, 1990, 6, 357-361.
17. Nikolova, P.; Ward, O. P. Effect of Support Matrix on Ratio of Product to Byproduct Formation in l-Phenylacetyl Carbinol Synthesis. Biotechnol. Lett. 1994, 16, 7-10.
18. Webb, C.; Dervakos, G. A. Studies in Viable Cell Immobilization; R. G. Landes Co.: Austin, TX, 1996.
19. Windholz, M.; Buhavari, S.; Blumetti, R. F.; Otterbein, E. S. The Merck Index. 10th ed.; Merck & Co., Inc.: Rahway, NJ, 1983; p 909.
20. Yang, F.-X.; Gainer, J. L.; Carta, G. Asymmetric Reduction of Acetophenone with Nylon-Immobilized Baker's Yeast in Organic Solvents. Internal Report, University of Virginia, 1997.
21. Alberts, B.; Bray, D.; Lewis, J.; Raff, M.; Roberts, K.; Watson, J. D. Molecular Biology of the Cell; Garland Publishing: New York, 1994.
22. Nakamura, K.; Kondo, S.; Kawai, Y.; Ohno, A. Reduction by Baker's Yeast in Benzene. Tetrahedron Lett. 1991, 32, 7075-7078.
23. Klibanov, A. M. Enzymes that Work in Organic Solvents. Chemtech 1986 (June), 354-359.
24. Lorraine, K.; King, S.; Greasham, R.; Chartrain, M. Asymmetric Bioreduction of a Ketosulfone to the Corresponding Trans-Hydroxysulfone by the Yeast Rhodotorula rubra MY 2169. Enzyme Microb. Technol. 1996, 18, 1-6.
25. Secundo, F.; Phillips, R. S. Effects of Enantiospecificity of Alcohol Dehydrogenases from Thermoanaerobacter ethanolicus and Horse Liver. Enzyme Microb. Technol. 1996, 19, 487-492.
26. Adolph, H. W.; Kiefer, M.; Zeppezauer, M. The Influence of pH on the Substrate Specificity and Stereoselectivity of Alcohol Dehydrogenase from Horse Liver. In Enzymology and Molecular Biology of Carbonyl Metabolism 4; Plenum Press: New York, 1993.
27. Adlercreutz, P. Oxidation of trans- and cis-1,2-Cyclohexanediol by Gluconbacter oxidans. Appl. Microbiol. Biotechnol. 1989, 30, 257-263.
28. Alexandre, S.; Boutelet, I.; Vincent, J. C. pH Control of Dehydrogenase Systems. Enzyme Microb. Technol. 1988, 10, 479-485.
29. Froment, G. F.; Bischoff, K. B. Chemical Reactor Analysis and Design, 2nd ed.; John Wiley & Sons: New York, 1990.