Nad+-dependent (s)-specific secondary alcohol dehydrogenase involved in stereoinversion of 3-pentyn-2-ol catalyzed by nocardia fusca AKU 2123

Bioscience, Biotechnology and Biochemistry

Volumn 63, Issue 10, 1999, Pages 1721-1729

  Xie, Sheng Xue ^a   Ogawa, Jun ^a   Shimizu, Sakayu ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Acetylenic alcohol; Nocardia fusca; Secondary alcohol dehydrogenase; Stereoinversion; Stereospecific reduction

Indexed keywords

3 PENTYN 2 OL; 3-PENTYN-2-OL; ALCOHOL DEHYDROGENASE; ALKYNE; NICOTINAMIDE ADENINE DINUCLEOTIDE;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL MODEL; CHEMISTRY; ENZYME SPECIFICITY; ENZYMOLOGY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; KINETICS; METABOLISM; MOLECULAR GENETICS; NOCARDIA; PH; SEQUENCE HOMOLOGY; STEREOISOMERISM; TEMPERATURE;

ALCOHOL DEHYDROGENASE; ALKYNES; AMINO ACID SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROGEN-ION CONCENTRATION; KINETICS; MODELS, CHEMICAL; MOLECULAR SEQUENCE DATA; NAD; NOCARDIA; SEQUENCE HOMOLOGY, AMINO ACID; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TEMPERATURE;

EID: 0033203225     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.63.1721     Document Type: Article

References (24)

1. Glänzer, B. I., Faber, K., and Griengl, H., Enantioselective hydrolysis by baker’s yeast-III. Microbial resolution of alkynyl esters using lyophilized yeast. Tetrahedron, 43, 5791-5796 (1987).
2. Burgess, K. and Jennings, L. D., Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp. J. Am. Chem. Soc., 113, 6129-6139 (1991).
3. Shimizu, M., Kawanami, H., and Fujisawa, T., A lipase mediated asymmetric hydrolysis of 3-acyloxy-l-octyns and 3-(E)-acyloxy-l-octens. Chem. Lett., 107-110 (1992).
4. Ogawa, J., Xie, S.-X., and Shimizu, S., Production of (i?)-3-pentyn-2-ol through stereospecific hydrolysis of racemic 3-pen-tyn-2-ol esters with microbial enzymes. Appl. Microbiol. Biotechnol., 51, 53-57 (1999).
5. Xie, S.-X., Ogawa, J., and Shimizu, S., (S)-3-Pentyn-2-ol production through microbial enzyme-catalyzed, highly enantioselective hydrolysis of racemic 3-pentyn-2-ol esters. Biotechnol. Lett., 20, 935-938 (1998).
6. Ogawa, J., Xie, S.-X., and Shimizu, S., Stereoinversion of optically active 3-pentyn-2-ol byNocardiaspecies. Biotechnol. Lett., 21, 331-335 (1999).
7. Xie, S.-X., Ogawa, J., and Shimizu, S., Production of (R)-3-pentyn-2-ol through stereoinversion of racemic 3-pentyn-2-ol by Nocardia fusca AKU 2123. Appl. Microbiol. Biotechnol. in press (1999).
8. Ogawa, J., Soong, C.-L., Honda, M., and Shimizu, S., Imidase, a dihydropyrimidinase-like enzyme involved in the metabolism of cyclic imides. Eur. J. Biochem., 243, 322-327 (1997).
9. Shimizu, S., Kataoka, M., Chung, M. C.-M., and Yamada, H., Ketopantoic acid reductase of Pseudomonas maltophilia 845: purification and characterization, and role in pantothenate biosynthesis. J. Biol. Chem., 263, 12077-12084 (1988).
10. Shimizu, S., Kataoka, M., Katoh, M., Morikawa, T., Miyoshi, T., and Yamada, H., Stereoselective reduction of ethyl 4-chloro-3-oxobutanoate by a microbial aldehyde reductase in an organic solvent-water diphasic system. Appl. Environ. Microbiol., 56, 2374-2377 (1990).
11. Kataoka, M., Rohani, L. P. S., Yamamoto, K., Wada, M., Kawabata, H., Kita, K., Yanase, H., and Shimizu, S., Enzymatic production of ethyl (i?)-4-chloro-3-hydroxybutanoate: asymmetric reduction of ethyl 4-chloro-3-oxobutanoate by an Escherichia coli transformant expressing the aldehyde reductase gene from yeast. Appl. Microbiol. Biotechnol., 48, 699-703 (1997).
12. Zelinski, T., Peters, J., and Kula, M.-R., Purification and characterization of a novel carbonyl reductase isolated from Rhodococcus erythropolis. J. Biotechnol., 33, 283-292 (1994).
13. Itoh, N., Morihama, R., Wang, J.-C., Okada, K., and Mizuguchi, N., Purification and characterization of phenylacetal-dehyde reductase from a styrene-assimilating Corynebacterium strain, ST-10. Appl. Environ. Microbiol., 63, 3783-3788 (1997).
14. Peters, J., Minuth, T., and Kula, M.-R., Kinetic and mechanistic studies of a novel carbonyl reductase isolated from Candida parapsilosis. Biocatalysis, 8, 31-46 (1993).
15. Zelinski, T. and Kula, M.-R., A kinetic study and application of a novel carbonyl reductase isolated from Rhodococcus erythropolis. Bioorg. Med. Chem., 2, 421-428 (1994).
16. Itoh, N., Mizuguchi, N., and Mabuchi, M., Production of chiral alcohols by enantioselective reduction with NADH-dependent phenylacetaldehyde reductase from Corynebacterium strain ST-10. J. Molec. Catal. B: Enzymatic, 6, 41-50 (1999).
17. Bränden, C.-I., Jörnvall, H., Eklund, H., and Furugren, B., Alcohol dehydrogenases. In “The Enzymes, 3rd edn., Vol. 11”, ed. by Boyer, P. D., Academic Press, New York, pp. 103-190 (1975).
18. Muheim, A., Waldner, R., Sanglard, D., Reiser, J., Schoemaker, H. E., and Leisola, M. S. A., Purification and properties of an aryl-alcohol dehydrogenase from the white-rot fungus Phanerochaete chrysosporium. Eur. J. Biochem., 195, 369-375 (1991).
19. Shaw, J. P., Rekik, M., Schwager, F., and Harayama, S., Kinetic studies on benzyl alcohol dehydrogenase encoded by TOL plasmid pWWO. J. Biol. Chem., 268, 10842-10850 (1993).
20. Hummel, W., Reduction of acetophenone to i?(+)-phenylethanol by a new alcohol dehydrogenase from Lactobacillus kefir. Appl. Microbiol. Biotechnol., 34, 15-19 (1990).
21. Ludwig, B., Akundi, A., and Kendall, K., A long-chain secondary alcohol dehydrogenase from Rhodococcus erythropolis ATCC 4277. Appl. Environ. Microbiol., 61, 3729-3733 (1995).
22. Hummel, W. and Riebel, B., Chiral alcohols by enantioselective enzymatic oxidation. Ann. N.Y. Acad. Sei., Vol. 799 (Enzyme Engineering 13) 713-716 (1996).
23. Peters, J., Mimuth, T., and Kula, M.-R., A novel NADH-depen-dent carbonyl reductase with an extremely broad substrate range from Candida parapsilosis: purification and characterization. Enzyme. Microb. Technol., 15, 950-958 (1993).
24. Hummel, W., New alcohol dehydrogenases for the synthesis of chiral compounds. Adv. Biochem. Eng. Biotechnol., 58, 144-184 (1997).