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Literature summary for 1.1.1.1 extracted from
- Asymmetric ketone reduction by a hyperthermophilic alcohol dehydrogenase. The substrate specificity, enantioselectivity and tolerance of organic solvents (2006), Tetrahedron Asymmetry, 17, 3010-3014 .
No PubMed abstract available
Application
| Application | Comment | Organism |
|---|---|---|
| synthesis | the alcohol dehydrogenase from Pyrococcus furiosus is a very robust enzyme in some organic solvents. From a synthetic point of view, this property is particularly important and useful for the reduction of ketones with a low solubility in aqueous buffers | Pyrococcus furiosus |
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| expression in Escherichia coli | Pyrococcus furiosus |
Organic Solvent Stability
| Organic Solvent | Comment | Organism |
|---|---|---|
| dimethyl sulfoxide | the enzyme shows a high tolerance of organic solvents, this property is particularly important and useful for the reduction of ketones with a low solubility in aqueous buffers | Pyrococcus furiosus |
| hexane | the enzyme shows a high tolerance of organic solvents, this property is particularly important and useful for the reduction of ketones with a low solubility in aqueous buffers | Pyrococcus furiosus |
| isopropanol | the enzyme shows a high tolerance of organic solvents, this property is particularly important and useful for the reduction of ketones with a low solubility in aqueous buffers | Pyrococcus furiosus |
| methyl-tert-butylether | the enzyme shows a high tolerance of organic solvents, this property is particularly important and useful for the reduction of ketones with a low solubility in aqueous buffers | Pyrococcus furiosus |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Pyrococcus furiosus | E7FHL9 | - |
- |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
| recombinant enzyme | Pyrococcus furiosus |
Storage Stability
| Storage Stability | Organism |
|---|---|
| 4°C, stable for 4 months | Pyrococcus furiosus |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| ethyl (2,4-dichlorophenyl)(oxo)acetate + NADH + H+ | the enzyme catalyzes the reduction of aromatic alpha-ketoesters to the corresponding enantiomerically pure (R)-configured alpha-hydroxyesters | Pyrococcus furiosus | ethyl (2R)-(2,4-dichlorophenyl)(hydroxy)acetate + NAD+ | - |
? |  |
| ethyl (3,5-difluorophenyl)(oxo)acetate + NADH + H+ | the enzyme catalyzes the reduction of aromatic alpha-ketoesters to the corresponding enantiomerically pure (R)-configured alpha-hydroxyesters | Pyrococcus furiosus | ethyl (2R)-(3,5-difluorophenyl)(hydroxy)acetate + NAD+ | - |
? | |
| ethyl (4-bromophenyl)(oxo)acetate + NADH + H+ | the enzyme catalyzes the reduction of aromatic alpha-ketoesters to the corresponding enantiomerically pure (R)-configured alpha-hydroxyesters | Pyrococcus furiosus | ethyl (2R)-(4-bromophenyl)(hydroxy)acetate + NAD+ | - |
? | |
| ethyl (4-chlorophenyl)(oxo)acetate + NADH + H+ | the enzyme catalyzes the reduction of aromatic alpha-ketoesters to the corresponding enantiomerically pure (R)-configured alpha-hydroxyesters | Pyrococcus furiosus | ethyl (2R)-(4-chlorophenyl)(hydroxy)acetate + NAD+ | - |
? | |
| ethyl (4-cyanophenyl)(oxo)acetate + NADH + H+ | the enzyme catalyzes the reduction of aromatic alpha-ketoesters to the corresponding enantiomerically pure (R)-configured alpha-hydroxyesters | Pyrococcus furiosus | ethyl (2R)-(4-cyanophenyl)(hydroxy)acetate + NAD+ | - |
? | |
| ethyl (4-fluorophenyl)(oxo)acetate + NADH + H+ | the enzyme catalyzes the reduction of aromatic alpha-ketoesters to the corresponding enantiomerically pure (R)-configured alpha-hydroxyesters | Pyrococcus furiosus | ethyl (2R)-(4-fluorophenyl)(hydroxy)acetate + NAD+ | - |
? | |
| ethyl (4-methylphenyl)(oxo)acetate + NADH + H+ | the enzyme catalyzes the reduction of aromatic alpha-ketoesters to the corresponding enantiomerically pure (R)-configured alpha-hydroxyesters | Pyrococcus furiosus | ethyl (2R)-hydroxy(4-methylphenyl)acetate + NAD+ | - |
? | |
| ethyl 3,3-dimethyl-2-oxobutanoate + NADH + H+ | enantioselectivity of the aliphatic a-ketoester reduction is moderate with the major product is the (S)-enantiomer, 71% enantiomeric excess of ethyl (2S)-2-hydroxy-3,3-dimethylbutanoate | Pyrococcus furiosus | ethyl (2R)-2-hydroxy-3,3-dimethylbutanoate + NAD+ | - |
? | |
| ethyl 3,3-dimethyl-2-oxobutanoate + NADH + H+ | enantioselectivity of the aliphatic a-ketoester reduction is moderate with the major product is the (S)-enantiomer, 71% enantiomeric excess of ethyl (2S)-2-hydroxy-3,3-dimethylbutanoate | Pyrococcus furiosus | ethyl (2S)-2-hydroxy-3,3-dimethylbutanoate + NAD+ | - |
? | |
| ethyl 3-methyl-2-oxobutanoate + NADH + H+ | enantioselectivity of the aliphatic a-ketoester reduction is moderate with the major product is the (S)-enantiomer, 44% enantiomeric excess of ethyl (2S)-2-hydroxy-3-methylbutanoate | Pyrococcus furiosus | ethyl (2R)-2-hydroxy-3-methylbutanoate + NAD+ | - |
? | |
| ethyl 3-methyl-2-oxobutanoate + NADH + H+ | enantioselectivity of the aliphatic a-ketoester reduction is moderate with the major product is the (S)-enantiomer, 44% enantiomeric excess of ethyl (2S)-2-hydroxy-3-methylbutanoate | Pyrococcus furiosus | ethyl (2S)-2-hydroxy-3-methylbutanoate + NAD+ | - |
? | |
| ethyl 3-oxo-3-phenylpropanoate + NADH + H+ | ethyl (3S)-3-hydroxy-3-phenylpropanoate is produced with 99% enantiomeric excess | Pyrococcus furiosus | ethyl (3S)-3-hydroxy-3-phenylpropanoate + NAD+ | - |
? | |
| ethyl 3-oxobutanoate + NADH + H+ | ethyl (3S)-3-hydroxybutanoate is produced with 95% enantiomeric excess | Pyrococcus furiosus | ethyl (3S)-3-hydroxybutanoate + NAD+ | - |
? | |
| ethyl 3-oxohexanoate + NADH + H+ | ethyl (3R)-3-hydroxyhexanoate is produced with 24% enantiomeric excess | Pyrococcus furiosus | ethyl (3R)-3-hydroxyhexanoate + NAD+ | - |
? | |
| ethyl 3-oxopentanoate + NADH + H+ | ethyl (3S)-3-hydroxypentanoate + NAD+is produced with 60% enantiomeric excess | Pyrococcus furiosus | ethyl (3S)-3-hydroxypentanoate + NAD+ | - |
? | |
| ethyl 4-chloro-3-oxobutanoate + NADH + H+ | ethyl (3R)-4-chloro-3-hydroxybutanoate is produced with 4% enantiomeric excess | Pyrococcus furiosus | ethyl (3R)-4-chloro-3-hydroxybutanoate + NAD+ | - |
? | |
| ethyl 4-methyl-3-oxopentanoate + NADH + H+ | ethyl (3S)-3-hydroxy-4-methylpentanoate is produced with 16% enantiomeric excess | Pyrococcus furiosus | ethyl (3S)-3-hydroxy-4-methylpentanoate + NAD+ | - |
? | |
| ethyl oxo(phenyl)acetate + NADH + H+ | the enzyme catalyzes the reduction of aromatic alpha-ketoesters to the corresponding enantiomerically pure (R)-configured alpha-hydroxyesters | Pyrococcus furiosus | ethyl (2R)-hydroxy(phenyl)acetate + NAD+ | - |
? | |
| additional information | the enzyme catalyzes the reduction of acetophenone derivatives to the corresponding (S)-chiral alcohols in an enantiomerically pure form. The substituents on the benzene ring of the aryl ketones exert some effect on the enzyme activity, although the influence is not dramatic. The enantioselectivity of the reduction is not affected by the substituents and pattern of the substitution. The alpha-chlorinated acetophenone shows a much higher activity than the unsubstituted one (more than 10 times) | Pyrococcus furiosus | ? | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| AdhD | - |
Pyrococcus furiosus |
| PFADH | - |
Pyrococcus furiosus |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 37 | - |
assay at | Pyrococcus furiosus |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 6.5 | - |
assay at | Pyrococcus furiosus |
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Release 2023.1 (January 2023)
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