Purification and Characterization of<i>α</i>-Keto Ester Reductases from Bakers’ Yeast

Nakamura, Kaoru; Kondo, Shinichi; Kawai, Yasushi; Nakajima, Nobuyoshi; Ohno, Atsuyoshi

doi:10.1271/bbb.58.2236

Cited by 43 publications

(16 citation statements)

References 4 publications

(6 reference statements)

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“…21) Since YKER-I, VI, and VII have a high reducing activity for -keto esters such as ethyl 4-chloroacetoacetate, these three YKER differ from our purified YKAR. Aliphatic -keto esters (ethyl 2-oxobutanoate, ethyl 2-oxopentanoate, ethyl 2-oxohexanoate, ethyl 2-oxoheptanoate, and ethyl 3-methyl-2-oxobutanoate) are not reduced by YKER-II.…”

Section: Comparison With Other Yeast Reductasesmentioning

confidence: 78%

Purification and Characterization of α-Keto Amide Reductase fromSaccharomyces cerevisiae

Ishihara

Yamamoto

Mitsuhashi

et al. 2004

Bioscience, Biotechnology, and Biochemistry

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Section: Comparison With Other Yeast Reductasesmentioning

confidence: 78%

Purification and Characterization of α-Keto Amide Reductase fromSaccharomyces cerevisiae

Ishihara

Yamamoto

Mitsuhashi

et al. 2004

Bioscience, Biotechnology, and Biochemistry

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“…Several enzymes with ethyl 3-oxobutanoate reducing activity have been purified from S. cerevisiae and characterized (Heidlas and Tressl, 1990;Heidlas et al, 1988;Nakamura et al, 1991Nakamura et al, , 1994Shieh and Sih, 1993;Shieh et al, 1985). Heidlas et al (1988) found for the main R-specific enzyme K m ‫ס‬ 17 mM and for the main S-specific enzyme K m ‫ס‬ 0.9 mM towards ethyl 3-oxobutanoate.…”

Section: Enantioselectivitymentioning

confidence: 99%

Influence of the ethanol and glucose supply rate on the rate and enantioselectivity of 3‐oxo ester reduction by baker's yeast

Chin-Joe

Straathof

Pronk

et al. 2001

Biotech & Bioengineering

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Baker's-yeast-mediated reductions of ketones hold great potential for the industrial production of enantiopure alcohols. In this article we describe the stoichiometry and kinetics of asymmetric ketone reduction by cell suspensions of bakers' yeast (Saccharomyces cerevisiae). A system for quantitative analysis of 3-oxo ester reduction was developed and allowed construction of full mass and redox balances as well as determination of the influence of different process parameters on aerobic ketone reduction. The nature of the electron donor (ethanol or glucose) and its specific consumption rate by the biomass (0-1 mol.kg dw(-1).h(-1)) affected the overall stoichiometry and rate of the process and the final enantiomeric excess of the product. Excess glucose as the electron donor, i.e. a very high consumption rate of glucose, resulted in a high rate of alcoholic fermentation, oxygen consumption, and biomass formation and therefore causing low efficiency of glucose utilization. Controlled supply of the electron donor at the highest rates applied prevented alcoholic fermentation but still resulted in biomass formation and a high oxygen requirement, while low rates resulted in a more efficient use of the electron donor. Low supply rates of ethanol resulted in biomass decrease while low supply rates of glucose provided the most efficient strategy for electron donor provision and yielded a high enantiomeric excess of ethyl (S)-3-hydroxybutanoate. In contrast to batchwise conversions with excess glucose as the electron donor, this strategy prevented by-product formation and biomass increase, and resulted in a low oxygen requirement.

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“…18) This high specific activity of the earthworm extract is an advantage for the reduction of -keto esters. As the alkyl chain length of the substrate molecule ( -keto esters) become longer, the reducing activity decreased.…”

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confidence: 99%

Stereoselective Reduction of Carbonyl Compounds Using the Cell-Free Extract of the Earthworm,Lumbricus rubellus, as a Novel Source of Biocatalyst

Ishihara

Nakajima

2006

Bioscience, Biotechnology, and Biochemistry

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We found the reducing activity toward carbonyl compounds in the cell-free extract of the earthworm, Lumbricus rubellus. The earthworm extract had a reducing activity for keto esters in the presence of NADH or NADPH as a coenzyme. The earthworm extract reduced ethyl 3-methyl-2-oxobutanoate to the corresponding alcohol with a high enantiomeric excess (91%, R-form) at 50 C in the presence of NADH. In particular, ethyl 2-oxoheptanoate was exclusively reduced to the corresponding (R)-hydroxyl ester with a high enantiomeric excess (> 99%).

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Purification and Characterization ofα-Keto Ester Reductases from Bakers’ Yeast

Cited by 43 publications

References 4 publications

Purification and Characterization of α-Keto Amide Reductase fromSaccharomyces cerevisiae

Purification and Characterization of α-Keto Amide Reductase fromSaccharomyces cerevisiae

Influence of the ethanol and glucose supply rate on the rate and enantioselectivity of 3‐oxo ester reduction by baker's yeast

Stereoselective Reduction of Carbonyl Compounds Using the Cell-Free Extract of the Earthworm,Lumbricus rubellus, as a Novel Source of Biocatalyst

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