Stereoselective reduction of ethyl 4-chloro-3-oxobutanoate by Escherichia coli transformant cells coexpressing the aldehyde reductase and glucose dehydrogenase genes

Applied Microbiology and Biotechnology

Volumn 51, Issue 4, 1999, Pages 486-490

  Kataoka, M ^a   Yamamoto, K ^a   Kawabata, H ^a   Wada, M ^a,c   Kita, K ^b   Yanase, H ^b   Shimizu, S ^a  

^a KYOTO UNIVERSITY   (Japan)

^b TOTTORI UNIVERSITY   (Japan)

^c FUKUI PREFECTURAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOACETIC ACID DERIVATIVE; ALDEHYDE REDUCTASE; GLUCOSE DEHYDROGENASE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; ORGANIC SOLVENT; WATER;

ARTICLE; BACILLUS MEGATERIUM; BACTERIAL GENE; BACTERIUM TRANSFORMATION; CATALYST; ENANTIOMER; ESCHERICHIA COLI; GENE EXPRESSION; NONHUMAN; REDUCTION; STEREOCHEMISTRY;

ACETOACETATES; ALDEHYDE REDUCTASE; BACILLUS; ESCHERICHIA COLI; GLUCOSE 1-DEHYDROGENASE; GLUCOSE DEHYDROGENASES; MITOSPORIC FUNGI; OXIDATION-REDUCTION; PLASMIDS; STEREOISOMERISM; TRANSFORMATION, BACTERIAL;

BACILLUS MEGATERIUM; BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; NEGIBACTERIA; SPORIDIOBOLUS SALMONICOLOR;

EID: 0032951737     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s002530051421     Document Type: Article

References (20)

1. Bradford MM (1976) 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
2. Chang ACY, Cohen SN (1978) Construction and characterization of amplifiable multicopy DNA cloning vehicles derived from the P15 A cryptic miniplasmid. J Bacteriol 134: 1141-1156
3. Devaux-Basseguy R, Bergel A, Comta M (1997) Potential applications of NAD(P)-dependent oxidoreductases in synthesis: a survey. Enzyme Microb Technol 20: 248-258
4. Grunwald J, Wirz B, Scollar MP, Klibanov AM (1986) Asymmetric oxidoreductions catalyzed by alcohol dehydrogenase in organic solvents. J Am Chem Soc 108: 6732-6734
5. Hummel W, Kula MR (1989) Dehydrogenases for the synthesis of chiral compounds. Eur J Biochem 184: 1-13
6. Kataoka M, Sakai H, Morikawa T, Katoh M, Miyoshi T, Shimizu S, Yamada H (1992) Characterizaion of aldehyde reductase of Sporobolomyces salmonicolor. Biochim Biophys Acta 1122: 57-62
7. Kataoka M, Rohani LPS, Yamamoto K, Wada M, Kawabata H, Kita K, Yanase H, Shimizu S (1997) Enzymatic production of ethyl (R)-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
8. Kataoka M, Rohani LPS, Wada M, Kita K, Yanase H, Urabe I, Shimizu S (1998) Escherichia coli transformant expressing the glucose dehydrogenase gene from Bacillus megaterium as a co-factor regenerator in a chiral alcohol production system. Biosci Biotech Biochem 62: 167-169
9. Kita K, Matsuzaki K, Hashimoto T, Yanase H, Kato N, Chung MCM, Kataoka M, Shimizu S (1996) Cloning of the aldehyde reductase gene from a red yeast, Sporobolomyces salmonicolor, and characterization of the gene and its product. Appl Environ Microbiol 62: 2303-2310
10. Makino Y, Negoro S, Urabe I, Okada H (1989) Stability-increasing mutants of glucose dehydrogenase from Bacillus megaterium IWG3. J Biol Chem 264: 6381-6385
11. Rose RE (1988) The nucleotide sequence of pACYC177. Nucleic Acids Res 16: 356
12. Shieh WR, Gopalan AS, Sih CJ (1985) Stereochemical control of yeast reductions. 5. Characterization of the oxidoreductases involved in the reduction of β-keto esters. J Am Chem Soc 10: 2993-2994
13. Shimizu S, Yamada H (1992) Enzymatic synthesis of chiral intermediates for D-pantothenate synthesis. In: Heinemann R, Walnak B (eds) Opportunities with industrial enzymes. Walnak, Chicago, pp 22-37
14. Shimizu S, Kataoka M, Katoh M, Morikawa T, Miyoshi T, Yamada H (1990a) 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
15. Shimizu S, Kataoka M, Morishita A, Katoh M, Morikawa T, Miyoshi T, Yamada H (1990b) Microbial asymmetric reduction of ethyl 4-chloro-3-oxobutanoate to optically active ethyl 4-chloro-3-hydroxybutanoate. Biotechnol Lett 12: 593-596
16. Wong CH, Drueckhammer DG, Sweers HM (1985) Enzyme vs. fermentative synthesis: thermostable glucose dehydrogenase catalyzed regeneration of NAD(P)H for use in enzymatic synthesis. J Am Chem Soc 107: 4028-4031
17. Yamada H, Shimizu S (1988) Microbial and enzymatic processes for the production of biologically and chemically useful compounds. Angew Chem Int Ed Eng 27: 622-642
18. Yamada H, Shimizu S (1992) Microbial and enzymatic processes for the production of biologically and chemically useful compounds. In: Yoshida Z, Ohshiro Y (eds) New aspects of organic chemistry II. Kodansha, Tokyo, pp 455-468
19. Yamada H, Shimizu S, Kataoka M, Sakai H, Miyoshi T (1990) A novel NADPH-dependent aldehyde reductase, catalyzing asymmetric reduction of β-keto acid esters, from Sporobolomyces salmonicolor: purification and characterization. FEMS Microbiol Lett 70: 45-48
20. Zhou B, Gopalan AS, VanMiddlesworth F, Shieh WR, Sih CJ (1983) Stereochemical control of yeast reductions. 1. Asymmetric synthesis of L-carnitine. J Am Chem Soc 105: 5925-5926