Asymmetric bioreduction of a keto ester to its corresponding (S)- hydroxy ester by Microbacterium sp. MB 5614

Journal of Fermentation and Bioengineering

Volumn 81, Issue 6, 1996, Pages 530-533

  Roberge, Christopher ^a   King, Anthony ^a   Pecore, Victor ^a   Greasham, Randolph ^a   Chartrain, Michel ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

asymmetric bioreduction; biocatalysis; bioprocess; biotransformation; MK 0476

Indexed keywords

ESTER DERIVATIVE; LEUKOTRIENE RECEPTOR BLOCKING AGENT; PEPTIDOLEUKOTRIENE;

ARTICLE; ASTHMA; BACTERIAL GROWTH; BACTERIUM; BIOTRANSFORMATION; CATALYST; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER;

BACTERIA (MICROORGANISMS); MICROBACTERIUM SP.;

EID: 0029908583     PISSN: 0922338X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0922-338X(96)81474-7     Document Type: Article

References (22)

1. Ariens, E.: Nonchiral, homochiral and composite chiral drugs. Trends Biochem. Sci., 14, 68-76 (1993).
2. Rauws, A. and Groen, K.: Current regulatory (draft) guidance on chiral medicinal products: Canada, EEC, Japan, United States. Chirality, 6, 72-75 (1994).
3. Stinson, S.: Chiral drugs. Chem. Eng. News, Sept. 38-72 (1994).
4. Jones, J. B.: Enzymes in organic synthesis. Tetrahedron, 42, 3351-3403 (1986).
5. Kieslich, K.: Biotransformations of industrial use. Acta Biotechnol., 11, 559-570 (1991).
6. Lilly, M.: Advances in biotransformation processes. Chemical Eng. Sci., 49, 151-159 (1994).
7. Margolin, A.: Enzymes in the synthesis of chiral drugs. Enzyme Microb. Technol., 15, 266-280 (1993).
8. Csuk, R. and Glanzer, B.: Baker's yeast mediated transformations in organic chemistry. Chem. Rev., 91, 49-97 (1991).
9. Nakamura, K., Kawai, Y., Kitayama, T., Miyai, T., Ogawa, M., Mikata, Y., Higaki, M., and Ohno, A.: Asymmetric reduction of ketones with microbes. Bull. Inst. Chem. Res., Kyoto Univ., 67, 157-168 (1989).
10. Servi, S.: Baker's yeast as a reagent in organic synthesis. Synthesis, 1, 1-25 (1990).
11. Ward, O. and Young, C.: Reductive biotransformations of organic compounds by cells or enzymes of yeast. Enzyme Microb. Technol., 12, 482-492 (1990).
12. Peters, J., Zelinski, T., and Kulla, M.: Studies on the distribution and regulation of microbial keto ester reductases. Appl. Microb. Biotechnol., 28, 334-340 (1992).
13. Christen, M., Crout, D., Holt, R., Morris, J., and Simon, H.: Biotransformations using clostridia: stereospecific reductions of a β-ketoester. J. Chem. Soc. Perkin Trans., 1, 491-493 (1992).
14. Gauthier, J., Jones, T., Champion, E., Charette, L., Dehaven, R., Ford-Hutchinson, A., Hoogsteen, K., Lord, A., Masson, P., Piechuta, H., Pong, S., Springer, J., Therien, M., Zamboni, R., and Young, R.: Stereospeciflc synthesis, assignement of absolute configuration, and biological activity of the enantiomers of 3-[[[3-[2-(7-chloroquinolin-2-yl)-(E)-ethenyl]phenyl] [[3-(dimethylamino)3-oxopropyl]thio]methyl]thio]propionic acid, a potent and specific leukotriene D4 receptor antagonist. J. Med. Chem., 33, 2841 (1990).
15. King, A., Corley, E., Anderson, R., Larsen, R., Verhoeven, T., and Reider, P.: An efficient synthesis of LTD4 antagonist L-699,392. J. Org. Chem., 58, 3731-3735 (1993).
16. Hunt, J., Carter, A., Murrell, J., Dalton, H., Hallinan, K., Crout, D., Holt, R., and Crosby, J.: Yeast catalyzed reduction of β-ketoesters. I. Factors affecting whole-cell catalytic activity and stereoselectivity. Biocatal. Biotransf., 12, 159-178 (1995).
17. Vshio, K., Inouye, K., Nakamura, K., Oka, S., and Ohno, A.: Stereochemical control in microbial reduction. IV. Effect of cultivation conditions on the reduction of β-keto esters by methylotrophic yeasts. Tetrahedron Lett., 27, 2657-2660 (1986).
18. Kometani, T., Kitatsuji, E., and Matsuno, R.: Baker's yeast mediated bioreduction: practical procedure using ethanol as energy source. J. Ferment. Bioeng., 71, 187-199 (1991).
19. Box, G. and Draper, R.: Empirical model-building and response surface. J. Wiley and Sons, New York, USA (1987).
20. Katz, L., King, S., Greasham, R., and Chartrain, M.: Asymmetric bioreduction of a ketosulfone to the corresponding trans-hydroxysulfone by the yeast Rhodotorula rubra MY 2169. Enzyme Microb. Technol. (1996). in press
21. Reddy, J., Tschaen, D., Shi, V.J., Pecore, V., Katz, L., Greasham, R., and Chartrain, M.: Asymmetric bioreduction of a β-tetralone to its corresponding (5)-alcohol by the yeast Trichosporon capitatum MY 1890. J. Ferment. Bioeng., 81, 304-309 (1996).
22. Wipf, B., Kupfer, E., Bertazzi, R., and Leuenberger, H.: Production of (+)-(S)-ethyl 3-hydroxybutyrate and (-)-(R)ethyl 3-hydroxybutyrate by microbial reduction of ethyl acetoacetate. Helv. Chim. Acta, 66, 485-488 (1983).