1.1.1.320: benzil reductase [(S)-benzoin forming]
This is an abbreviated version!
For detailed information about benzil reductase [(S)-benzoin forming], go to the full flat file.
Word Map on EC 1.1.1.320
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1.1.1.320
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reductases
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pichia
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ketoreductase
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sepiapterin
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stereoselective
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cereus
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enantioselective
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non-conventional
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synthesis
- 1.1.1.320
- reductases
-
pichia
- ketoreductase
- sepiapterin
-
stereoselective
- cereus
-
enantioselective
-
non-conventional
- synthesis
Reaction
Synonyms
benzil reductase, KRED1-Pglu
ECTree
1.1.1.320 benzil reductase [(S)-benzoin forming]Advanced search results
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results (Substrates Products
Substrates Products on EC 1.1.1.320 - benzil reductase [(S)-benzoin forming]
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1-(2-fluorophenyl)ethanone + NADPH + H+
(1S)-1-(2-fluorophenyl)ethanol + NADP+
76% of the rate with 1-(4-nitrophenyl)ethanone, 97% yield, 94% enantiomeric excess
-
-
?
1-(2-nitrophenyl)ethanone + NADPH + H+
(1S)-1-(2-nitrophenyl)ethanol + NADP+
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+
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+
-
-
-
-
?
1-(4-methyl-phenyl)-2-phenyl-ethane-1,2-dione + NADPH + H+
? + NADP+
-
-
-
-
?
1-(4-nitrophenyl)ethanone + NADPH + H+
(1S)-1-(4-nitrophenyl)ethanol + NADP+
100% yield, 98% enantiomeric excess
-
-
?
1-(furan-2-yl)ethanone + NADPH + H+
(1S)-1-(furan-2-yl)ethanol + NADP+
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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+
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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+
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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+
-
51% of the activity with benzil, 95% yield, 98% enantiomeric excess
-
?
2-acetylbenzonitrile + NADPH + H+
2-[(1S)-1-hydroxyethyl]benzonitrile + NADP+
82% of the rate with 1-(4-nitrophenyl)ethanone, 98% yield, 98% enantiomeric excess
-
-
?
2-hydroxy-1-phenyl-1-propanone + NADP+
1-phenylpropane-1,2-dione + NADPH + H+
-
-
-
-
?
3-oxo-3-phenylpropanenitrile + NADPH + H+
(3S)-3-hydroxy-3-phenylpropanenitrile + NADP+
-
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+
68% of the rate with 1-(4-nitrophenyl)ethanone, 70% yield, 97% enantiomeric excess
-
-
?
benzophenone + NADPH + H+
diphenylmethanol + NADP+
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66% yield
-
?
ethyl 2-oxo-2-phenylacetate + NADPH + H+
ethyl (2S)-hydroxy(phenyl)acetate + NADP+
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115% yield, 40% enantiomeric excess
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?
(S)-benzoin + NADP+
benzil + NADPH + H+
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stereospecific asymmetric reduction of benzil to (S)-benzoin
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-
r
(S)-benzoin + NADP+
benzil + NADPH + H+
stereospecific asymmetric reduction of benzil to (S)-benzoin
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r
(S)-benzoin + NADP+
benzil + NADPH + H+
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stereospecific asymmetric reduction of benzil to (S)-benzoin, recombinant Bacillus cereus benzil reductase produces optically pure (S)-benzoin with NADPH in vitro
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r
(S)-benzoin + NADP+
benzil + NADPH + H+
stereospecific asymmetric reduction of benzil to (S)-benzoin
-
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r
benzil + NADPH + H+
(S)-benzoin + NADP+
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98% enantiomeric excess
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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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?
additional information
?
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for the enantioselective reduction of mono-substituted acetophenones, reaction rates of meta- and para-derivatives are consistent with the electronic effects described by delta-Hammett coefficients. Enantioselectivity is determined by an opposite orientation of the substrate in the binding pocket. Reduction of ortho-derivatives occurs only with substrates bearing substituents with low steric impact, and reactivity is controlled by stereoelectronic features
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?
additional information
?
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for the enantioselective reduction of mono-substituted acetophenones, reaction rates of meta- and para-derivatives are consistent with the electronic effects described by delta-Hammett coefficients. Enantioselectivity is determined by an opposite orientation of the substrate in the binding pocket. Reduction of ortho-derivatives occurs only with substrates bearing substituents with low steric impact, and reactivity is controlled by stereoelectronic features
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?
additional information
?
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the enzyme prefers space-demanding substrates, which are often converted with high stereoselectivity
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?
additional information
?
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the enzyme prefers space-demanding substrates, which are often converted with high stereoselectivity
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?
additional information
?
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the enzyme is preferentiallly active on aromatic 1,2-diketones. It catalyzes the stereoselective monoreduction and desymmerization of bulky dicarbonyls. Mechanism and in silico prediction of substrates reactivity, overview
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additional information
?
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the enzyme is preferentiallly active on aromatic 1,2-diketones. It catalyzes the stereoselective monoreduction and desymmerization of bulky dicarbonyls. Mechanism and in silico prediction of substrates reactivity, overview
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