Yeast Reduction of Ethyl Acetoacetate: (
            <i>S</i>
            )‐( + )‐Ethyl 3‐Hydroxybutanoate

Seebàch, Dieter; Sutter, Marc; Weber, Roland H.; Züger, Max F.

doi:10.1002/0471264180.os063.01

Cited by 14 publications

(13 citation statements)

References 32 publications

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“…The observation that more glucose is needed than ethanol as cosubstrate fits previously reported whole cell bioreductions of carbonyl compounds. For example, in the first reported bioreduction of (i) BCO2,6D to BCO2one6ol (Mori and Nagano, 1990) and of (ii) ethylacetoacetate to (S)-ethyl-3-hydroxybutanoate (Kometani et al, 1991;Seebach et al, 1984), >200 g/L sucrose was needed to convert 5 to 10 g/L of the carbonyl substrates under anaerobic conditions. With ethanol as cosubstrate, the same amount of ethylacetoacetate was converted using ten times less ethanol (in grams per liter) as compared with glucose.…”

Section: Discussionmentioning

confidence: 99%

Efficient anaerobic whole cell stereoselective bioreduction with recombinant saccharomyces cerevisiae

Katz

Frejd

Hahn‐Hägerdal

et al. 2003

Biotech & Bioengineering

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In this study we investigate the NADPH-dependent stereoselective reduction of the bicyclic diketone bicyclo[2.2.2]octane-2,6-dione (BCO2,6D) to the chiral ketoalcohol (1R,4S,6S)-6-hydroxybicyclo[2.2.2]octane-2-one (BCO2one6ol). Our aim was to develop a whole cell batch process for reduction of carbonyl substrates with (i) a high cosubstrate yield (formed product/consumed cosubstrate) and (ii) a high conversion rate under anaerobic conditions with Saccharomyces cerevisiae as biocatalyst and glucose as cosubstrate. Five open reading frames (ORFs), YMR226c, YDR368w, YOR120w, YGL157w, and YGL039w, encoding reductases involved in the conversion of BCO2,6D were identified using cell-free extract from strains belonging to the ExClone collection (yeast ORF expression clones; ResGen, Invitrogen Corp., UK). We report the one-step purification and characterization of three major BCO2,6D reductases, YMR226cp, YDR368wp (YPR1p), and YOR120wp (GCY1p). The reductases were overexpressed under a strong constitutive promoter and the impact on cosubstrate yield, conversion time, glucose consumption rate, and reduction rate was investigated when reductases were overexpressed either alone or in combination with low phosphoglucose isomerase activity (encoded by YBR196c). Combining overexpression of BCO2,6D reductase with reduced glycolytic rate (low phosphoglucose isomerase activity) offers a fast whole cell stereoselective bioreduction system useful for facilitated anaerobic batch conversions.

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Section: Discussionmentioning

confidence: 99%

Efficient anaerobic whole cell stereoselective bioreduction with recombinant saccharomyces cerevisiae

Katz

Frejd

Hahn‐Hägerdal

et al. 2003

Biotech & Bioengineering

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“…There is an obvious structural relationship between these γ-ketoesters and β-ketoesters which have been selectively and efficiently reduced using baker's yeast, Saccharomyces cerevisiae 10 . Indeed this method has also been applied to a range of γ-ketoacids giving, after acid catalysed lactonization, the corresponding γ-substituted γ-lactones in 13-79% yield (R = n-alkyl: C 1 -C 5 , C 8 , C 11 and C 13 ) and with enantiomeric excesses which were consistently greater than 98% 11 .…”

Section: Resultsmentioning

confidence: 99%

A versatile kinetic alkylation-ozonolysis route for the synthesis of lactones: chiral γ-lactones and racemic δ-lactones

Geraghty¹,

Costello²

2003

Arkivoc

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A robust and versatile kinetic alkylation-ozonolysis procedure, previously used for the synthesis of 2-alkyl-2-cyclopenten-1-ones and racemic γ-substituted-γ-lactones, has now been applied to the synthesis of chiral γ-substituted-γ-lactones and δ-substituted-δ-lactones. In addition to the synthesis of lactones with simple alkyl substituents, the method allows terminal ester and halogen groups, and an alkyne bond to be incorporated into the side chain.

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“…As we expected, the cis fused lactone 12 predominates (78%). Due to the difficulties in isolation of the products from the concentrated yeast medium, reduction under more dilute conditions following a modification of the procedure described by Seebach 14 was next attempted (Table 1, entry 2, procedure B). Isolation of the products is easier from the less concentrated medium, resulting in higher yields.…”

Section: Methodsmentioning

confidence: 99%

Chemoenzymatic methods in the asymmetric synthesis of α-diazosulfoxides

Maguire¹,

Collins²,

Ford³

2003

Arkivoc

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Asymmetric synthesis of the sulfide lactones 12 and 13 in excellent enantiopurity is achieved by reduction of cyclohexanone derivative 10 using baker's yeast, followed by acid catalysed cyclisation. The outcome of the yeast reduction is very sensitive to the reaction conditions employed. Transformation of 12 to the α-diazosulfoxide 4 (≥98%ee) and rhodium acetate catalysed decomposition of this are also described.

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Yeast Reduction of Ethyl Acetoacetate: ( S )‐( + )‐Ethyl 3‐Hydroxybutanoate

Cited by 14 publications

References 32 publications

Efficient anaerobic whole cell stereoselective bioreduction with recombinant saccharomyces cerevisiae

Efficient anaerobic whole cell stereoselective bioreduction with recombinant saccharomyces cerevisiae

A versatile kinetic alkylation-ozonolysis route for the synthesis of lactones: chiral γ-lactones and racemic δ-lactones

Chemoenzymatic methods in the asymmetric synthesis of α-diazosulfoxides

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