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Literature summary extracted from

  • Rodriguez, S.; Kayser, M.M.; Stewart, J.D.
    Highly stereoselective reagents for beta-keto ester reductions by genetic engineering of bakers yeast (2001), J. Am. Chem. Soc., 123, 1547-1555.
    View publication on PubMed

Application

EC Number Application Comment Organism
1.1.1.283 synthesis engineeering of Sacharomyces cerevisiae for specific reduction of a variety of carbonyl compounds by altering the levels of fatty acid synthase Fas, aldo-keto reductase Ypr1 and R-acetoxy ketone reductase Gre2. By choosing the appropriate engineered yeast strain, it is possible to prepare many of the alcohols in high stereochemical purities and good chemical yields. For example, in the reductions of some alpha-unsubstituted beta-keto esters, genetically disabling Fas virtually eliminates production of (3R)-alcohols. Overexpressing (3S)-selective reductase Gre2 in the Fas knockout strain gives yeast cells that reduce these ketones to the corresponding (3S)-alcohols in >98% ee in each case Saccharomyces cerevisiae

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.283 Saccharomyces cerevisiae Q12068
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Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.283 ethyl (2R)-2-methyl-3-oxobutanoate + NADPH + H+
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 Saccharomyces cerevisiae ethyl (2R,3S)-3-hydroxy-2-methylbutanoate + NADP+ 86% yield, 70% (2R,3S)-enantiomer in a strain lacking fatty acid synthase activity and overexpressing Gre2 ?
1.1.1.283 ethyl 3-oxobutanoate + NADPH + H+
-
 Saccharomyces cerevisiae ethyl (3S)-3-hydroxybutanoate + NADP+ 83% yield, 98% S-enantiomer in a strain lacking fatty acid synthase activity and overexpressing Gre2 ?
1.1.1.283 ethyl 3-oxohexanoate + NADPH + H+
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 Saccharomyces cerevisiae ethyl (3S)-3-hydroxyhexanoate + NADP+ 90% yield, 98% S-enantiomer in a strain lacking fatty acid synthase activity and overexpressing Gre2 ?
1.1.1.283 ethyl 3-oxopentanoate + NADPH + H+
-
 Saccharomyces cerevisiae ethyl (3S)-3-hydroxypentanoate + NADP+ 87% yield, 98% S-enantiomer in a strain lacking fatty acid synthase activity and overexpressing Gre2 ?
1.1.1.283 methyl 3-oxobutanoate + NADPH + H+
-
 Saccharomyces cerevisiae methyl (3S)-3-hydroxybutanoate + NADP+ 76% yield, 98% S-enantiomer in a strain lacking fatty acid synthase activity and overexpressing Gre2 ?
1.1.1.283 methyl 3-oxopentanoate + NADPH + H+
-
 Saccharomyces cerevisiae methyl (3S)-3-hydroxypentanoate + NADP+ 85% yield, 98% S-enantiomer in a strain lacking fatty acid synthase activity and overexpressing Gre2 ?

Synonyms

EC Number Synonyms Comment Organism
1.1.1.283 Gre2
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 Saccharomyces cerevisiae