Information on EC 1.1.1.320 - benzil reductase [(S)-benzoin forming]

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
1.1.1.320
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RECOMMENDED NAME
GeneOntology No.
benzil reductase [(S)-benzoin forming]
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-benzoin + NADP+ = benzil + NADPH + H+
show the reaction diagram
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-
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SYSTEMATIC NAME
IUBMB Comments
(S)-benzoin:NADP+ oxidoreductase
The enzyme also reduces 1-phenylpropane-1,2-dione. The enzyme from Bacillus cereus in addition reduces 1,4-naphthoquinone and 1-(4-methylphenyl)-2-phenylethane-1,2-dione with high efficiency [2].
CAS REGISTRY NUMBER
COMMENTARY hide
422524-67-2
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
physiological function
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amino acid differences in the benzil reductase among Bacillus cereus strains
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(S)-benzoin + NADP+
benzil + NADPH + H+
show the reaction diagram
1-(2-fluorophenyl)ethanone + NADPH + H+
(1S)-1-(2-fluorophenyl)ethanol + NADP+
show the reaction diagram
76% of the rate with 1-(4-nitrophenyl)ethanone, 97% yield, 94% enantiomeric excess
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-
?
1-(2-nitrophenyl)ethanone + NADPH + H+
(1S)-1-(2-nitrophenyl)ethanol + NADP+
show the reaction diagram
53% of the rate with 1-(4-nitrophenyl)ethanone, 78% yield, 98% enantiomeric excess
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-
?
1-(3-fluorophenyl)ethanone + NADPH + H+
(1S)-1-(3-fluorophenyl)ethanol + NADP+
show the reaction diagram
61% of the rate with 1-(4-nitrophenyl)ethanone, 85% yield, 98% enantiomeric excess
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-
?
1-(4-fluoro-phenyl)-2-phenyl-ethane-1,2-dione + NADPH + H+
? + NADP+
show the reaction diagram
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-
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?
1-(4-methyl-phenyl)-2-phenyl-ethane-1,2-dione + NADPH + H+
? + NADP+
show the reaction diagram
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-
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-
?
1-(4-nitrophenyl)ethanone + NADPH + H+
(1S)-1-(4-nitrophenyl)ethanol + NADP+
show the reaction diagram
100% yield, 98% enantiomeric excess
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-
?
1-(furan-2-yl)ethanone + NADPH + H+
(1S)-1-(furan-2-yl)ethanol + NADP+
show the reaction diagram
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48% of the activity with benzil, 95% yield, 98% enantiomeric excess
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?
1-(pyridin-3-yl)ethanone + NADPH + H+
(S)-(1-pyridin-3yl)ethanol + NADP+
show the reaction diagram
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58% of the activity with benzil, 95% yield, 98% enantiomeric excess
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?
1-(pyridin-3-yl)propan-1-one + NADPH + H+
(S)-(1-pyridin-3-yl)propanol + NADP+
show the reaction diagram
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60% of the activity with benzil, 95% yield, 98% enantiomeric excess
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?
1-(thiophen-2-yl)ethanone + NADPH + H+
(1S)-1-(thiophen-2-yl)ethanol + NADP+
show the reaction diagram
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51% of the activity with benzil, 95% yield, 98% enantiomeric excess
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?
1-phenyl-1,2-propanedione + NADPH + H+
? + NADP+
show the reaction diagram
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-
-
-
?
2-acetylbenzonitrile + NADPH + H+
2-[(1S)-1-hydroxyethyl]benzonitrile + NADP+
show the reaction diagram
82% of the rate with 1-(4-nitrophenyl)ethanone, 98% yield, 98% enantiomeric excess
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?
2-hydroxy-1-phenyl-1-propanone + NADP+
1-phenylpropane-1,2-dione + NADPH + H+
show the reaction diagram
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?
3-oxo-3-phenylpropanenitrile + NADPH + H+
(3S)-3-hydroxy-3-phenylpropanenitrile + NADP+
show the reaction diagram
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55% of the activity with benzil, 95% yield, 95% enantiomeric excess
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?
4-acetylbenzonitrile + NADPH + H+
4-[(1S)-1-hydroxyethyl]benzonitrile + NADP+
show the reaction diagram
68% of the rate with 1-(4-nitrophenyl)ethanone, 70% yield, 97% enantiomeric excess
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?
benzil + NADPH + H+
(S)-benzoin + NADP+
show the reaction diagram
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98% enantiomeric excess
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?
benzophenone + NADPH + H+
diphenylmethanol + NADP+
show the reaction diagram
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66% yield
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?
ethyl 2-oxo-2-phenylacetate + NADPH + H+
ethyl (2S)-hydroxy(phenyl)acetate + NADP+
show the reaction diagram
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115% yield, 40% enantiomeric excess
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?
sec-phenethyl alcohol + NADP+
1-phenylethanone + NADPH + H+
show the reaction diagram
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(S)-benzoin + NADP+
benzil + NADPH + H+
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.042
1-phenyl-1,2-propanedione
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recombinant enzyme, pH 6.5, 37°C
0.64 - 0.768
benzil
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.75
1-phenyl-1,2-propanedione
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recombinant enzyme, pH 6.5, 37°C
0.14 - 1.07
benzil
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
65.33
1-phenyl-1,2-propanedione
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recombinant enzyme, pH 6.5, 37°C
0.22 - 1.4
benzil
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5
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assay at, reduction reaction
10
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assay at, oxidation reaction
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
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assay at
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6
90% of maximum activity
739919
8
90% of maximum activity
739919
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant enzyme from Escherichia coli strain DH5alpha by ammonium sulfate fractionation
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression of GFP-tagged enzyme in Bacillus cereus strain IFO3563, subcloning in Escherichia coli
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gene yueD, Bacillus cereus library screening in Escherichia coli and cloning of the gene encoding the benzil reductase, DNA and amino acid sequence determination and analysis, sequence comparisons, expression in Escherichia coli strain DH5alpha
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
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asymmetric reduction with Bacillus cereus benzil reductase can be utilized to produce important chiral compounds