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

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The expected taxonomic range for this enzyme is: Bacillus cereus

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EC NUMBER
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1.1.1.320
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RECOMMENDED NAME
GeneOntology No.
benzil reductase [(S)-benzoin forming]
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-benzoin + NADP+ = benzil + NADPH + H+
show the reaction diagram
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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].
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CAS REGISTRY NUMBER
COMMENTARY hide
422524-67-2
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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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
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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-(4-fluoro-phenyl)-2-phenyl-ethane-1,2-dione + NADPH + H+
? + NADP+
show the reaction diagram
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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-phenyl-1,2-propanedione + NADPH + H+
? + NADP+
show the reaction diagram
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-
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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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?
sec-phenethyl alcohol + NADP+
1-phenylethanone + NADPH + H+
show the reaction diagram
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?
additional information
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the enzyme is also active with 1,4-naphthoquinone, dichlone, and 4-phenylbenzaldehyde, substrate specificity, overview. 1-acenaphthenol is oxidized, although the kcat/Km ratio is low. No activity with progesterone, daunorubicin, and menaquinone. No or poor activity with benzyl phenyl ketone, benzophenone, dibenzoylmethane, chalcone, 1-phenyl-1,3-butanedione, diacetyl, 3,4-hexanedione, and acetophenone
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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
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
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LITERATURE
IMAGE
0.042
1-phenyl-1,2-propanedione
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recombinant enzyme, pH 6.5, 37°C
0.768
benzil
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recombinant enzyme, pH 6.5, 37°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.75
1-phenyl-1,2-propanedione
Bacillus cereus
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recombinant enzyme, pH 6.5, 37°C
1.07
benzil
Bacillus cereus
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recombinant enzyme, pH 6.5, 37°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
65.33
1-phenyl-1,2-propanedione
Bacillus cereus
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recombinant enzyme, pH 6.5, 37°C
3675
1.4
benzil
Bacillus cereus
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recombinant enzyme, pH 6.5, 37°C
1673
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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
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
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assay at
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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
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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
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LINKS TO OTHER DATABASES (specific for EC-Number 1.1.1.320)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)