1.1.1.304: diacetyl reductase [(S)-acetoin forming]
This is an abbreviated version!
For detailed information about diacetyl reductase [(S)-acetoin forming], go to the full flat file.
Word Map on EC 1.1.1.304
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1.1.1.304
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lactis
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alpha-dicarbonyls
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2,3-pentanedione
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pigeon
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l-xylulose
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xylitol
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alpha-acetolactate
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diacetylactis
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lager
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s-acetoin
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synthesis
- 1.1.1.304
- lactis
-
alpha-dicarbonyls
- 2,3-pentanedione
- pigeon
- l-xylulose
- xylitol
- alpha-acetolactate
- diacetylactis
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lager
-
s-acetoin
- synthesis
Reaction
Synonyms
acetoin(diacetyl) reductase, ADH, AdR, ADS1, ardII, BSDR, budC, DAR, diacetyl reductase, EC 1.1.1.5, FQU75_06005, Kp-BudC, Kpdar, NADH-dependent Kp-BudC, Ppdar, ReADR, S-stereospecific diacetyl reductase
ECTree
1.1.1.304 diacetyl reductase [(S)-acetoin forming]Advanced search results
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results (Substrates Products
Substrates Products on EC 1.1.1.304 - diacetyl reductase [(S)-acetoin 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
(3S)-acetoin + NADH + H+
(2S,3S)-2,3-butanediol + NAD+
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97% of the activity with diacetyl
97.3% enantiomeric excess and 96.5% diastereomeric excess
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r
1,2-propanediol + NAD+
? + NADH + H+
-
-
0.5% of the activity with 2,3-butanediol
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r
2,3-hexanedione + NADH + H+
? + NAD+
-
-
66% of the activity with diacetyl
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?
2,3-pentanedione + beta-NADH + H+
L-3-hydroxy-2-pentanone + beta-NAD+
-
-
-
-
ir
2,3-pentanedione + NADH + H+
? + NAD+
-
-
69% of the activity with diacetyl
-
?
3,4-hexanedione + NADH + H+
? + NAD+
-
-
10% of the activity with diacetyl
-
?
diacetyl + beta-NADH + H+
(S)-acetoin + beta-NAD+
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86.9% of the activity with pentane-2,3-dione
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-
ir
diacetyl + NADH + H+
(3S)-acetoin + NAD+
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97.3% enantiomeric excess
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ir
ethyl pyruvate + beta-NADH + H+
? + beta-NAD+
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38.4% of the activity with pentane-2,3-dione
-
-
ir
ethyl pyruvate + NADH + H+
? + NAD+
-
57.7% of the activity with diacetyl
-
-
?
methyl glyoxal + NADH + H+
? + NAD+
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11% of the activity with diacetyl
-
-
?
methyl pyruvate + beta-NADH + H+
? + beta-NAD+
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22.8% of the activity with pentane-2,3-dione
-
-
ir
methyl pyruvate + NADH + H+
? + NAD+
-
49% of the activity with diacetyl
-
-
?
2,3-pentanedione + NADH + H+
3-hydroxy-2-pentanone + NAD+
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85.6% of the activity with diacetyl
-
-
?
2,3-pentanedione + NADH + H+
3-hydroxy-2-pentanone + NAD+
77% of the (R)-2,3-butanediol dehydrogenase activity with substrate acetoin
-
-
?
diacetyl + NADH + H+
(S)-acetoin + NAD+
stereospecific reaction
-
-
?
diacetyl + NADH + H+
(S)-acetoin + NAD+
87% of the (R)-2,3-butanediol dehydrogenase activity with substrate acetoin
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-
?
additional information
?
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enzyme shows oxidative activity to racemic 2,3-butanediol but no activity toward racemic acetoin in the presence of NAD+
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-
?
additional information
?
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the enzyme shows an S-enantioselectivity in the reversible reduction of acetoin so it might be responsible of the meso-butenediol formation from R-acetoin. It acts on racemic acetoin and (S)-acetoin to form (2S,3S)-butane-2,3-diol, EC 1.1.1.76, but also on the (2R,3R)-butane-2,3-diol isomer in the reverse reaction, EC 1.1.1.4
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-
?
additional information
?
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the enzyme shows an S-enantioselectivity in the reversible reduction of acetoin so it might be responsible of the meso-butenediol formation from R-acetoin. It acts on racemic acetoin and (S)-acetoin to form (2S,3S)-butane-2,3-diol, EC 1.1.1.76, but also on the (2R,3R)-butane-2,3-diol isomer in the reverse reaction, EC 1.1.1.4
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-
?
additional information
?
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KpDAR has clear activities towards diacetyl, (R)/(S)-acetoin (cf. EC 1.1.1.303) and meso-2,3-butanediol with NADH/NAD+ as the cofactor. Diacetyl is the best substrate in the ketone reduction reactions. meso-2,3-Butanediol is the best substrate in the alcohol oxidation reactions, while very low activity is observed with (R)/(S)-acetoin, (2S,3S)-2,3-butanediol (EC 1.1.1.76) and (2R,3R)-2,3-butanediol (EC 1.1.1.4). Optimization of the reaction conditions, overview. Chiral-column GC analyses of products produced by whole-cells of recombinant Escherichia coli
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additional information
?
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the enzyme BudC also catalyzes the reduction of acetoin by NADH, cf. EC 1.1.1.76
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-
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additional information
?
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enzyme shows activity as a reductase specific for (S)-acetoin, EC 1.1.1.76, and both diacetyl reductase (EC 1.1.1.304) and NAD+-dependent alcohol dehydrogenase (EC 1.1.1.1) activities
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-
?
additional information
?
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enzyme shows activity as a reductase specific for (S)-acetoin, EC 1.1.1.76, and both diacetyl reductase (EC 1.1.1.304) and NAD+-dependent alcohol dehydrogenase (EC 1.1.1.1) activities
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-
?
additional information
?
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KC505218
the enzyme also catalyzes the stereospcific reaction of (S)-acetoin reduction to butanediol, EC 1.1.1.76
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-
?
additional information
?
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the enzyme also catalyzes the stereospcific reaction of (S)-acetoin reduction to butanediol, EC 1.1.1.76
-
-
?
additional information
?
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KC505218
the enzyme also catalyzes the stereospcific reaction of (S)-acetoin reduction to butanediol, EC 1.1.1.76
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-
?
additional information
?
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the enzyme also catalyzes the stereospcific reaction of (S)-acetoin reduction to butanediol, EC 1.1.1.76
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-
?
additional information
?
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Rhodococcus erythropolis WZ010 is capable of producing optically pure (2S,3S)-2,3-butanediol in alcoholic fermentation.
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?
additional information
?
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Rhodococcus erythropolis WZ010 is capable of producing optically pure (2S,3S)-2,3-butanediol in alcoholic fermentation.
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-
?
additional information
?
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the enzyme displays absolute stereospecificity in the reduction of diacetyl to (2S,3S)-2,3-butanediol via (S)-acetoin. The enzyme shows higher catalytic efficiency for (S)-1-phenylethanol oxidation than that for acetophenone reduction. ReADR-catalyzed asymmetric reduction of diacetyl is coupled with stereoselective oxidation of 1-phenylethanol, which simultaneously forms both (2S,3S)-2,3-butanediol and (R)-1-phenylethanol in great conversions and enantiomeric excess values.The enzyme accepts a broad range of substrates including aliphatic and aryl alcohols, aldehydes, and ketones
-
-
?
additional information
?
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the enzyme displays absolute stereospecificity in the reduction of diacetyl to (2S,3S)-2,3-butanediol via (S)-acetoin. The enzyme shows higher catalytic efficiency for (S)-1-phenylethanol oxidation than that for acetophenone reduction. ReADR-catalyzed asymmetric reduction of diacetyl is coupled with stereoselective oxidation of 1-phenylethanol, which simultaneously forms both (2S,3S)-2,3-butanediol and (R)-1-phenylethanol in great conversions and enantiomeric excess values.The enzyme accepts a broad range of substrates including aliphatic and aryl alcohols, aldehydes, and ketones
-
-
?
additional information
?
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-
Rhodococcus erythropolis WZ010 is capable of producing optically pure (2S,3S)-2,3-butanediol in alcoholic fermentation.
-
-
?
additional information
?
-
-
the enzyme displays absolute stereospecificity in the reduction of diacetyl to (2S,3S)-2,3-butanediol via (S)-acetoin. The enzyme shows higher catalytic efficiency for (S)-1-phenylethanol oxidation than that for acetophenone reduction. ReADR-catalyzed asymmetric reduction of diacetyl is coupled with stereoselective oxidation of 1-phenylethanol, which simultaneously forms both (2S,3S)-2,3-butanediol and (R)-1-phenylethanol in great conversions and enantiomeric excess values.The enzyme accepts a broad range of substrates including aliphatic and aryl alcohols, aldehydes, and ketones
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-
?
additional information
?
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no activity with alpha-NADH or NADPH
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-
?
