Purification and characterization of a yeast carbonyl reductase for synthesis of optically active (R)-styrene oxide derivatives

Bioscience, Biotechnology and Biochemistry

Volumn 69, Issue 1, 2005, Pages 79-86

  Kizaki, Noriyuki ^a   Sawa, Ikuo ^a   Yano, Miho ^a   Yasohara, Yoshihiko ^a   Hasegawa, Junzo ^a  

^a KANEKA CORPORATION   (Japan)

Author keywords

Carbonyl reductase; Enantioselective reduction; Rhodotorula glutinis; Styrene oxide

Indexed keywords

ALCOHOLS; CHARACTERIZATION; DERIVATIVES; ELECTROPHORESIS; MICROORGANISMS; PURIFICATION; REDUCTION; STEREOCHEMISTRY; STYRENE; SYNTHESIS (CHEMICAL); YEAST;

CARBONYL COMPOUNDS; HOMOGENEITY; PHENACYL HALIDES; STEREOSELECTIVE REDUCTION;

ENZYMES;

ALCOHOL DEHYDROGENASE; CARBONYL REDUCTASE (NADPH); EPOXIDE; STYRENE OXIDE;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ENZYME SPECIFICITY; ENZYMOLOGY; ISOLATION AND PURIFICATION; METABOLISM; MOLECULAR GENETICS; RHODOTORULA; STEREOISOMERISM;

ALCOHOL OXIDOREDUCTASES; AMINO ACID SEQUENCE; EPOXY COMPOUNDS; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; RHODOTORULA; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

RHODOTORULA DAIRENENSIS; RHODOTORULA GLUTINIS;

EID: 15244342654     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.69.79     Document Type: Article

References (25)

1. Ainsworth, A. T., and Smith, D. G., European Patent Application 28105 (May 6, 1981).
2. Pedragosa-Moreau, S., Archelas, A., and Furstoss, R., Enantiocomplementary epoxide hydrolyses as a preparative access to both enantiomers of styrene oxide. J. Org. Chem., 58, 5533-5536 (1993).
3. Kutsuki, H., Sawa, I., Hasegawa, J., and Watanabe, K., Asymmetric hydrolysis of (dl)-1-acyloxy-2-halo-1-phenylethanes with lipases. Agric. Biol. Chem., 50, 2369-2373 (1986).
4. Tanaka, K., and Yasuda, M., A practical synthesis of (R)-chlorostyrene oxide starting from 3-chloroethylbenzene. Tetrahedron: Asymmetry, 9, 3275-3282 (1998).
5. Hamada, H., Miura, T., Kumobayashi, H., Matsuda, T., Harada, T., and Nakamura, K., Asymmetric synthesis of (R)-2-chloro-1-(m-chlorophenyl)ethanol using acetone powder of Geotrichum candidum. Biotechnol. Lett., 23, 1603-1606 (2001).
6. Barbieri, C., Bossi, L., D'Arrigo, P., Fantoni, G. P., and Servi, S., Bioreduction of aromatic ketones: preparation of chiral benzyl alcohols in both enantiomeric forms. J. Mol. Cat. B: Enzymatic, 11, 415-421 (2001).
7. Ema, T., Moriya, H., Kofukuda, T., Ishida, T., Maehara, K., Utaka, M., and Sakai, T., High enantioselectivity and broad substrate specificity of a carbonyl reductase: toward a versatile biocatalyst. J. Org. Chem., 66, 8682-8684 (2001).
8. De Carvalho, M., Okamoto, M. T., Samenho Moran, P. J., and Rodrigues, J. A. R., Baker's yeast reduction of α-haloacetophenones. Tetrahedron, 47, 2073-2080 (1991).
9. Itoh, N., Matsuda, M., Mabuchi, M., Dairi, T., and Wang, J., Chiral alcohol production by NADH-dependent phenylacetaldehyde reductase coupled with in situ regeneration of NADH. Eur. J. Biochem., 269, 2394-2402 (2002).
10. Kataoka, M., Kita, K., Wada, M., Yasohara, Y., Hasegawa, J., and Shimizu, S., Novel bioreduction system for the production of chiral alcohols. Appl. Microbiol. Biotechnol., 62, 437-445 (2003).
11. Badford, M. M., A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem., 72, 248-254 (1976).
12. Wermuth, B., Purification and properties of NADPH-dependent carbonyl reductase from human brain. J. Biol. Chem., 256, 1206-1213 (1981).
13. Ris, M. M., and von Wartburg, J.-P., Heterogeneity of NADPH-dependent aldehyde reductase from human and rat brain. Eur. J. Biochem., 37, 69-77 (1973).
14. Kori, K. K., Yearby, C., Scott, W., and Donaldson, O. K., Purification and properties of three separate menadione reductases from hog liver. J. Biol. Chem., 244, 621-629 (1969).
15. Zhou, B., Gopalan, A. S., van Middlesworth, F., Shieh, W. R., and Sih, C. J., Stereochemical control of yeast reduction. 1. Asymmetric synthesis of L-carnitine. J. Am. Chem. Soc., 105, 5925-5926 (1983).
16. Ogawa, J., and Shimizu, S., Industrial microbial enzymes: their discovery by screening and use in large-scale production of useful chemicals in Japan. Curr. Opin. Biochem., 13, 367-375 (2002).
17. Itoh, N., Morikawa, R., Wang, J., Okada, K., and Mizuguchi, N., Purification and characterization of phenylacetaldehyde reductase from a styrene-assimilating Corynebacterium strain, ST-10. Appl. Environ. Microbiol., 63, 3783-3788 (1997).
18. Hummel, W., New alcohol dehydrogenases for the synthesis of chiral compounds. Adv. Biochem. Eng./Biotechnol., 58, 145-184 (1997).
19. Kataoka, M., Sakai, H., Morikawa, T., Katoh, M., Miyoshi, T., Shimizu, S., and Yamada, H., Characterization of aldehyde reductase of Sporobolomyces salmonicolor. Biochim. Biophys. Acta, 1122, 57-62 (1992).
20. Hidalgo, A.-R. G. D., Akond, M. A., Kita, K., Kataoka, M., and Shimizu, S., Isolation and primary structural analysis of two conjugated polyketone reductases from Candida parapsilosis. Biosci. Biotechnol. Biochem., 65, 2785-2788 (2001).
21. Kataoka, M., Doi, Y., Sim, T.-S., Shimizu, S., and Yamada, H., A novel NADPH-dependent carbonyl reductase of Candida macedoniensis: purification and characterization. Arch. Biochem. Biophys., 294, 469-474 (1992).
22. Kataoka, M., Shimizu, S., and Yamada, H., Carbonyl reductases: their functions and application to the production of optically active compounds. Hakkokougaku (in Japanese), 70, 479-493 (1992).
23. Liu, X., Zhu, T.-S., Sun, P.-D., and Xu, J.-H., Asymmetric reduction of aromatic ketones by the baker's yeast in organic solvent systems. Synth. Commun., 31, 1521-1526 (2001).
24. Goswami, A., Bezbaruah, L. R., Borthakur, N., Dey, D., and Hazarika, K. A., Microbial reduction of ω-bromo-acetophenones in the presence of surfactants. Tetrahedron: Asymmetry, 11, 3701-3709 (2000).
25. Kizaki, N., Yasohara, Y., Hasegawa, J., Wada, M., Kataoka, M., and Shimizu, S., Synthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate by Escherichia coli transformant cells coexpressing carbonyl reductase and glucose dehydrogenase. Appl. Microbiol. Biotechnol., 55, 590-595 (2001).