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Information on EC 1.1.1.76 - (S,S)-butanediol dehydrogenase
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1.1.1.76 (S,S)-butanediol dehydrogenaseIUBMB Comments
This enzyme catalyses the reversible reduction of (S)-acetoin to (S,S)-butane-2,3-diol. It can also catalyse the irreversible reduction of diacetyl to (S)-acetoin.
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Word Map
- 1.1.1.76
- saccharolyticum
-
s-acetoin
-
brevibacterium
- synthesis
-
corynebacterium
-
klebsiella
- pneumoniae
-
s-configuration
- chimera
The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
Synonyms
l-bdh, 2,3-bdh, (s,s)-butanediol dehydrogenase, acetoin(diacetyl) reductase, s-2,3-butanediol dehydrogenase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(2R,3R)-2,3-BDH
(2R,3R)-2,3-butanediol dehydrogenase
(S,S)-2,3-butanediol dehydrogenase
(S,S)-butanediol dehydrogenase
2,3-butanediol dehydrogenase
acetoin(diacetyl) reductase
AdR
BDH
budC
ButA
L(+)-2,3-butanediol dehydrogenase (L-acetoin forming)
-
-
-
-
L-BDH
L-butanediol dehydrogenase
-
-
-
-
S-2,3-butanediol dehydrogenase
additional information
L-BDH
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2S,3S)-butane-2,3-diol + NAD+ = (S)-acetoin + NADH + H+
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
-
,
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SYSTEMATIC NAME
IUBMB Comments
(S,S)-butane-2,3-diol:NAD+ oxidoreductase
This enzyme catalyses the reversible reduction of (S)-acetoin to (S,S)-butane-2,3-diol. It can also catalyse the irreversible reduction of diacetyl to (S)-acetoin.
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CAS REGISTRY NUMBER
COMMENTARY
37250-14-9
-
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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
(2S,3S)-2,3-butanediol + NAD+
(3S)-acetoin + NADH + H+
-
-
-
?
(2S,3S)-2,3-butanediol + NAD+
(R,S)-acetoin + NADH + H+
-
selective catalysis of S,S- and meso-butanediol, but not R,R-butanediol
-
r
(R,S)-acetoin + NADH + H+
(2S,3S)-2,3-butanediol + meso-2,3-butanediol + NAD+
-
-
-
r
(R,S)-acetoin + NADPH
(2S,3S)-2,3-butanediol + meso-2,3-butanediol + NADP+
-
-
Ara1p is selective toward the acetoin carbonyl group, leading to an S-alcohol
-
r
1,2-propanediol + NAD+
?
-
0.57% activity compared to (2S,3S)-butane-2,3-diol
-
-
?
1-phenylpropanol + NAD+
1-phenylpropan-1-one + NADH + H+
-
-
-
?
2 diacetyl + 2 NADH + 2 H+
(3S)-acetoin + (2S,3S)-butane-2,3-diol + NAD+
-
-
-
-
?
2 rac acetoin + 2 NADH + 2 H+
(2S,3S)-butane-2,3-diol + (2R,3S)-butane-2,3-diol + 2 NAD+
-
-
-
-
?
2,3-hexanedione + NADH + H+
?
-
66% activity compared to diacetyl
-
-
?
3,4-hexanedione + NADH + H+
?
-
10% activity compared to diacetyl
-
-
?
diacetyl + NADH + H+
?
-
35% activity in comparison to L-acetoin
-
-
r
L-acetoin + NADH + H+
(S,S)-butane-2,3-diol + NAD+
-
100% activity
-
-
r
meso-2,3-butanediol + NAD+
(R,S)-acetoin + NADH + H+
-
selective catalysis of S,S- and meso-butanediol, but not R,R-butanediol
-
r
meso-2,3-butanediol + NAD+
acetoin + NADH
poor substrate
-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
preferred substrate
-
-
r
(2S)-acetoin + NADH + H+
(2S,3S)-butane-2,3-diol + NAD+
-
97% activity compared to diacetyl
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-
r
(2S)-acetoin + NADH + H+
(2S,3S)-butane-2,3-diol + NAD+
-
-
-
-
r
(2S)-acetoin + NADH + H+
(2S,3S)-butane-2,3-diol + NAD+
-
-
-
-
r
(2S,3S)-butane-2,3-diol + NAD+
(2S)-acetoin + NADH + H+
-
100% activity
-
-
r
(2S,3S)-butane-2,3-diol + NAD+
(2S)-acetoin + NADH + H+
-
-
-
-
r
(2S,3S)-butane-2,3-diol + NAD+
(2S)-acetoin + NADH + H+
-
-
-
-
r
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
stereoselective interconversion
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
stereoselective interconversion
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
-
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
stereoselective interconversion
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
-
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
stereoselective interconversion
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
-
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
stereoselective interconversion
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
-
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
stereoselective interconversion
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
-
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
stereoselective interconversion
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
-
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
stereoselective interconversion
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
the enzyme displayed absolute stereospecificity in the reduction of diacetyl to (2S,3S)-2,3-butanediol via (S)-acetoin. Physiological role in favor of (2S,3S)-2,3-butanediol formation
-
-
r
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
the enzyme displays absolute stereospecificity in the reduction of diacetyl to (2S,3S)-2,3-butanediol via (S)-acetoin. Under the optimized conditions, the activity of diacetyl reduction is 11.9fold higher than that of (2S,3S)-2,3-butanediol oxidation
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-
r
(S,S)-butane-2,3-diol + NAD+
L-acetoin + NADH + H+
-
-
-
-
?
1,3-dihydroxyacetone + NADH + H+
?
-
low activity with 30 mM
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-
?
1,3-dihydroxyacetone + NADH + H+
?
-
low activity with 30 mM
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-
?
2,3-pentanedione + NADH + H+
?
-
69% activity compared to diacetyl
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-
?
2,3-pentanedione + NADH + H+
?
-
7% activity in comparison to L-acetoin
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r
2,3-pentanedione + NADH + H+
?
-
7% activity in comparison to L-acetoin
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-
r
diacetyl + NADH
L-acetoin + NAD+
-
also reduction of 2,3-pentanedione
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?
diacetyl + NADH
L-acetoin + NAD+
-
also reduction of 2,3-pentanedione
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?
glyceraldehyde + NADH + H+
?
-
low activity with 30 mM
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-
?
L-acetoin + NADH
L-2,3-butanediol
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stereoisomeric specificity for hydroxyl group in L configuration
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?
L-acetoin + NADH
L-2,3-butanediol
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reaction dependent of substrate concentration, incubation time, glucose addition, aeration
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r
L-acetoin + NADH
L-2,3-butanediol
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short chain dehydrogenase reductase family
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r
L-acetoin + NADH
L-2,3-butanediol
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short chain dehydrogenase reductase family
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r
L-acetoin + NADH
L-2,3-butanediol
-
no oxidadion of several alcohols
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r
L-acetoin + NADH
L-2,3-butanediol
-
exhibits marked sequence similarity and common functionally conserved sequence with meso-enzyme
-
r
L-acetoin + NADH
L-2,3-butanediol
-
in presence of adequate amounts of NAD+ and hydrazine and in an alkaline condition acetoin formation is much in favour, acetoin concentrations have no appreciable influence on dehydrogenation of L-butanediol
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r
L-acetoin + NADH
L-2,3-butanediol
-
in presence of adequate amounts of NAD+ and hydrazine and in an alkaline condition acetoin formation is much in favour, acetoin concentrations have no appreciable influence on dehydrogenation of L-butanediol
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r
L-acetoin + NADH
L-2,3-butanediol
-
reaction dependent of substrate concentration, incubation time, glucose addition, aeration
-
r
L-acetoin + NADH
L-2,3-butanediol
-
short chain dehydrogenase reductase family
-
r
L-acetoin + NADH
L-2,3-butanediol
-
exhibits marked sequence similarity and common functionally conserved sequence with meso-enzyme
-
r
L-acetoin + NADH
L-2,3-butanediol
-
short chain dehydrogenase reductase family
-
r
L-acetoin + NADH
L-2,3-butanediol
-
no oxidadion of several alcohols
-
r
L-acetoin + NADH
L-2,3-butanediol
-
stereoisomeric specificity for hydroxyl group in L configuration
-
?
L-acetoin + NADH + H+
(S,S)-butanediol + NAD+
-
To confirm the high production of enzyme, the conversion of L-acetoin, in a racemic mixture, to L-2,3-butanediol is studied. 0.37% L-2,3-butanediol is formed from 1% L-acetoin added to the culture.
-
-
?
L-acetoin + NADH + H+
(S,S)-butanediol + NAD+
-
To confirm the high production of enzyme, the conversion of L-acetoin, in a racemic mixture, to L-2,3-butanediol is studied. 0.37% L-2,3-butanediol is formed from 1% L-acetoin added to the culture.
-
-
?
additional information
?
-
-
the enzyme shows no activity toward racemic acetoin in the presence of NAD+ as well as no activity with NADPH, 1,4-butanediol, 2,5-hexanedione, 2,4-pentanedione, 2-butanone, methanol, mannitol, and glycerol
-
-
?
additional information
?
-
-
not: meso-butanediol, D-butanediol, 2-butanol, 1,2-propanediol, ethanol, acetol, 1,2-butanediol, 1,3-butanediol, n-butanol, n-propanol, D-acetoin, acetol, dihydroxyacetone, 2,4-pentanedione
-
-
?
additional information
?
-
-
not: meso-butanediol, D-butanediol, 2-butanol, 1,2-propanediol, ethanol, acetol, 1,2-butanediol, 1,3-butanediol, n-butanol, n-propanol, D-acetoin, acetol, dihydroxyacetone, 2,4-pentanedione
-
-
?
additional information
?
-
the meso-2,3-butanediol dehydrogenase from Klebsiella pneumoniae is active with meso-2,3-butanediol, but also with (2S,3S)-butane-2,3-diol converting them to (3R)-acetoin and (3S)-acetoin, respectively. Additionally the enzyme also has diacetyl reductase [(S)-acetoin forming] activity (EC 1.1.1.304)
-
-
-
additional information
?
-
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
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
although the gene encoding (S,S)-2,3-butanediol dehydrogenase is found in the genome of Paenibacillus brasilensis strain PB24, only R,R-2,3-butanediol ((R,R)-2,3-butanediol dehydrogenase, EC 1.1.1.4) and meso-2,3-butanediol are detected by gas chromatography under the growth conditions (modified YEPD medium, pH 6.3, 32°C, up to 72 h)
-
-
-
additional information
?
-
-
although the gene encoding (S,S)-2,3-butanediol dehydrogenase is found in the genome of Paenibacillus brasilensis strain PB24, only R,R-2,3-butanediol ((R,R)-2,3-butanediol dehydrogenase, EC 1.1.1.4) and meso-2,3-butanediol are detected by gas chromatography under the growth conditions (modified YEPD medium, pH 6.3, 32°C, up to 72 h)
-
-
-
additional information
?
-
-
no activity with (2R,3R)-butane-2,3-diol and (2R,3S)-butane-2,3-diol, and no activity with 1,3-butanediol, 1,2-pentanediol, 1,3-propanediol, and glycerol in the oxidation reaction. No activity with 2,4-pentanedione, butanone, 2,5-hexanedione, and 1,3-dihydroxypropanone in the reduction reaction. Substrate specificity, overview. (2S,3S)-2,3-BDH reduces diacetyl into (3S)-acetoin and (2S,3S)-2,3-BD, while racemic acetoin is reduced to form (2S,3S)-2,3-BD and meso-2,3-BD
-
-
-
additional information
?
-
-
no activity with (2R,3R)-butane-2,3-diol and (2R,3S)-butane-2,3-diol, and no activity with 1,3-butanediol, 1,2-pentanediol, 1,3-propanediol, and glycerol in the oxidation reaction. No activity with 2,4-pentanedione, butanone, 2,5-hexanedione, and 1,3-dihydroxypropanone in the reduction reaction. Substrate specificity, overview. (2S,3S)-2,3-BDH reduces diacetyl into (3S)-acetoin and (2S,3S)-2,3-BD, while racemic acetoin is reduced to form (2S,3S)-2,3-BD and meso-2,3-BD
-
-
-
additional information
?
-
-
no activity with (2R,3R)-butane-2,3-diol and (2R,3S)-butane-2,3-diol, and no activity with 1,3-butanediol, 1,2-pentanediol, 1,3-propanediol, and glycerol in the oxidation reaction. No activity with 2,4-pentanedione, butanone, 2,5-hexanedione, and 1,3-dihydroxypropanone in the reduction reaction. Substrate specificity, overview. (2S,3S)-2,3-BDH reduces diacetyl into (3S)-acetoin and (2S,3S)-2,3-BD, while racemic acetoin is reduced to form (2S,3S)-2,3-BD and meso-2,3-BD
-
-
-
additional information
?
-
-
no activity with (2R,3R)-butane-2,3-diol and (2R,3S)-butane-2,3-diol, and no activity with 1,3-butanediol, 1,2-pentanediol, 1,3-propanediol, and glycerol in the oxidation reaction. No activity with 2,4-pentanedione, butanone, 2,5-hexanedione, and 1,3-dihydroxypropanone in the reduction reaction. Substrate specificity, overview. (2S,3S)-2,3-BDH reduces diacetyl into (3S)-acetoin and (2S,3S)-2,3-BD, while racemic acetoin is reduced to form (2S,3S)-2,3-BD and meso-2,3-BD
-
-
-
additional information
?
-
-
no activity with (2R,3R)-butane-2,3-diol and (2R,3S)-butane-2,3-diol, and no activity with 1,3-butanediol, 1,2-pentanediol, 1,3-propanediol, and glycerol in the oxidation reaction. No activity with 2,4-pentanedione, butanone, 2,5-hexanedione, and 1,3-dihydroxypropanone in the reduction reaction. Substrate specificity, overview. (2S,3S)-2,3-BDH reduces diacetyl into (3S)-acetoin and (2S,3S)-2,3-BD, while racemic acetoin is reduced to form (2S,3S)-2,3-BD and meso-2,3-BD
-
-
-
additional information
?
-
-
no activity with (2R,3R)-butane-2,3-diol and (2R,3S)-butane-2,3-diol, and no activity with 1,3-butanediol, 1,2-pentanediol, 1,3-propanediol, and glycerol in the oxidation reaction. No activity with 2,4-pentanedione, butanone, 2,5-hexanedione, and 1,3-dihydroxypropanone in the reduction reaction. Substrate specificity, overview. (2S,3S)-2,3-BDH reduces diacetyl into (3S)-acetoin and (2S,3S)-2,3-BD, while racemic acetoin is reduced to form (2S,3S)-2,3-BD and meso-2,3-BD
-
-
-
additional information
?
-
-
no activity with (2R,3R)-butane-2,3-diol and (2R,3S)-butane-2,3-diol, and no activity with 1,3-butanediol, 1,2-pentanediol, 1,3-propanediol, and glycerol in the oxidation reaction. No activity with 2,4-pentanedione, butanone, 2,5-hexanedione, and 1,3-dihydroxypropanone in the reduction reaction. Substrate specificity, overview. (2S,3S)-2,3-BDH reduces diacetyl into (3S)-acetoin and (2S,3S)-2,3-BD, while racemic acetoin is reduced to form (2S,3S)-2,3-BD and meso-2,3-BD
-
-
-
additional information
?
-
-
no activity with (2R,3R)-butane-2,3-diol and (2R,3S)-butane-2,3-diol, and no activity with 1,3-butanediol, 1,2-pentanediol, 1,3-propanediol, and glycerol in the oxidation reaction. No activity with 2,4-pentanedione, butanone, 2,5-hexanedione, and 1,3-dihydroxypropanone in the reduction reaction. Substrate specificity, overview. (2S,3S)-2,3-BDH reduces diacetyl into (3S)-acetoin and (2S,3S)-2,3-BD, while racemic acetoin is reduced to form (2S,3S)-2,3-BD and meso-2,3-BD
-
-
-
additional information
?
-
the enzyme accepts a broad range of substrates including aliphatic and aryl alcohols, aldehydes, and ketones, overview. No activity with 4-chloroacetophenone, (R)-1-phenylethanol, and (2R,3R)-2,3-butanediol, poor activity with 3-methyl-2-acetophenone, 4-bromoacetophenone, 2-bromoacetophenone, benzaldehyde, and isophorone
-
-
?
additional information
?
-
-
the enzyme accepts a broad range of substrates including aliphatic and aryl alcohols, aldehydes, and ketones, overview. No activity with 4-chloroacetophenone, (R)-1-phenylethanol, and (2R,3R)-2,3-butanediol, poor activity with 3-methyl-2-acetophenone, 4-bromoacetophenone, 2-bromoacetophenone, benzaldehyde, and isophorone
-
-
?
additional information
?
-
the enzyme accepts a broad range of substrates including aliphatic and aryl alcohols, aldehydes, and ketones, overview. No activity with 4-chloroacetophenone, (R)-1-phenylethanol, and (2R,3R)-2,3-butanediol, poor activity with 3-methyl-2-acetophenone, 4-bromoacetophenone, 2-bromoacetophenone, benzaldehyde, and isophorone
-
-
?
additional information
?
-
-
the enzyme accepts a broad range of substrates including aliphatic and aryl alcohols, aldehydes, and ketones, overview. No activity with 4-chloroacetophenone, (R)-1-phenylethanol, and (2R,3R)-2,3-butanediol, poor activity with 3-methyl-2-acetophenone, 4-bromoacetophenone, 2-bromoacetophenone, benzaldehyde, and isophorone
-
-
?
additional information
?
-
-
meso-2,3-BDH from Serratia sp. T241 exhibits higher catalytic efficiency compared with the meso-2,3-BDHs from Klebsiella pneumoniae strain XJ-Li and Serratia marcescens strain H30. No activity is detected for (2R,3R)-2,3-BD as substrate by meso-2,3-BDH, but meso-2,3-BDH from Serratia sp. T241 can efficiently convert (2S,3S)-2,3-BD and meso-2,3-BD into (3S)-acetoin and (3R)-acetoin, respectively
-
-
-
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NATURAL SUBSTRATE
NATURAL 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
(2S)-acetoin + NADH + H+
(2S,3S)-butane-2,3-diol + NAD+
-
-
-
-
r
(2S,3S)-butane-2,3-diol + NAD+
(2S)-acetoin + NADH + H+
-
100% activity
-
-
r
(2S,3S)-butane-2,3-diol + NAD+
(2S)-acetoin + NADH + H+
-
-
-
-
r
(2S,3S)-butane-2,3-diol + NAD+
(2S)-acetoin + NADH + H+
-
-
-
-
r
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
-
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
-
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
-
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
-
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
-
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
-
-
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
the enzyme displayed absolute stereospecificity in the reduction of diacetyl to (2S,3S)-2,3-butanediol via (S)-acetoin. Physiological role in favor of (2S,3S)-2,3-butanediol formation
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NAD+
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NAD+
coenzyme binding motif T11G12XXXG16XG18 is conserved in the N-terminal region