1.1.1.76: (S,S)-butanediol dehydrogenase
This is an abbreviated version!
For detailed information about (S,S)-butanediol dehydrogenase, go to the full flat file.
Word Map on EC 1.1.1.76
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1.1.1.76
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saccharolyticum
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s-acetoin
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brevibacterium
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synthesis
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corynebacterium
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klebsiella
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pneumoniae
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s-configuration
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chimera
- 1.1.1.76
- saccharolyticum
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s-acetoin
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brevibacterium
- synthesis
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corynebacterium
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klebsiella
- pneumoniae
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s-configuration
- chimera
Reaction
Synonyms
(2R,3R)-2,3-BDH, (2R,3R)-2,3-butanediol dehydrogenase, (2S, 3S)-BDH, (2S, 3S)-butanediol dehydrogenase, (S,S)-2,3-BDH, (S,S)-2,3-butanediol dehydrogenase, (S,S)-butanediol dehydrogenase, 2,3-BDH, 2,3-butanediol dehydrogenase, acetoin(diacetyl) reductase, AdR, ADS1, ARA1, BDH, budC, ButA, L(+)-2,3-butanediol dehydrogenase (L-acetoin forming), L-(2S,3S)-butanediol dehydrogenase, L-BDH, L-butanediol dehydrogenase, LBDH, mbdh, meso-2,3-butanediol dehydrogenase, More, S-2,3-butanediol dehydrogenase
ECTree
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Substrates Products
Substrates Products on EC 1.1.1.76 - (S,S)-butanediol dehydrogenase
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REACTION DIAGRAM
(2S,3S)-2,3-butanediol + NAD+
(3S)-acetoin + NADH + H+
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-
?
(2S,3S)-2,3-butanediol + NAD+
(R,S)-acetoin + NADH + H+
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selective catalysis of S,S- and meso-butanediol, but not R,R-butanediol
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r
(R,S)-acetoin + NADH + H+
(2S,3S)-2,3-butanediol + meso-2,3-butanediol + NAD+
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r
(R,S)-acetoin + NADPH
(2S,3S)-2,3-butanediol + meso-2,3-butanediol + NADP+
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Ara1p is selective toward the acetoin carbonyl group, leading to an S-alcohol
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r
1,2-propanediol + NAD+
?
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0.57% activity compared to (2S,3S)-butane-2,3-diol
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-
?
1-phenylpropanol + NAD+
1-phenylpropan-1-one + NADH + H+
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?
2 diacetyl + 2 NADH + 2 H+
(3S)-acetoin + (2S,3S)-butane-2,3-diol + NAD+
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?
2 rac acetoin + 2 NADH + 2 H+
(2S,3S)-butane-2,3-diol + (2R,3S)-butane-2,3-diol + 2 NAD+
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?
2,3-hexanedione + NADH + H+
?
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66% activity compared to diacetyl
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?
3,4-hexanedione + NADH + H+
?
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10% activity compared to diacetyl
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?
diacetyl + NADH + H+
?
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35% activity in comparison to L-acetoin
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r
L-acetoin + NADH + H+
(S,S)-butane-2,3-diol + NAD+
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100% activity
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r
meso-2,3-butanediol + NAD+
(R,S)-acetoin + NADH + H+
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selective catalysis of S,S- and meso-butanediol, but not R,R-butanediol
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r
meso-2,3-butanediol + NAD+
acetoin + NADH
poor substrate
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-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
preferred substrate
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r
(2S,3S)-butane-2,3-diol + NAD+
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97% activity compared to diacetyl
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r
(2S)-acetoin + NADH + H+
(2S,3S)-butane-2,3-diol + NAD+
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r
(2S)-acetoin + NADH + H+
(2S,3S)-butane-2,3-diol + NAD+
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r
(2S)-acetoin + NADH + H+
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100% activity
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r
(2S,3S)-butane-2,3-diol + NAD+
(2S)-acetoin + NADH + H+
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-
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r
(2S,3S)-butane-2,3-diol + NAD+
(2S)-acetoin + NADH + H+
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-
-
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r
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
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stereoselective interconversion
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-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
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stereoselective interconversion
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-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
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-
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
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stereoselective interconversion
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-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
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-
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
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stereoselective interconversion
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?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
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-
-
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?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
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stereoselective interconversion
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?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
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-
-
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?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
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stereoselective interconversion
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?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
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-
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?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
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stereoselective interconversion
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-
?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
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-
-
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?
(2S,3S)-butane-2,3-diol + NAD+
(S)-acetoin + NADH + H+
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stereoselective interconversion
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?
(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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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+
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?
?
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low activity with 30 mM
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?
1,3-dihydroxyacetone + NADH + H+
?
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low activity with 30 mM
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?
?
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69% activity compared to diacetyl
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?
2,3-pentanedione + NADH + H+
?
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7% activity in comparison to L-acetoin
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r
2,3-pentanedione + NADH + H+
?
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7% activity in comparison to L-acetoin
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r
L-acetoin + NAD+
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also reduction of 2,3-pentanedione
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?
diacetyl + NADH
L-acetoin + NAD+
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also reduction of 2,3-pentanedione
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?
glyceraldehyde + NADH + H+
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low activity with 30 mM
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?
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
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no oxidadion of several alcohols
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r
L-acetoin + NADH
L-2,3-butanediol
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exhibits marked sequence similarity and common functionally conserved sequence with meso-enzyme
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r
L-acetoin + NADH
L-2,3-butanediol
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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
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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
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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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exhibits marked sequence similarity and common functionally conserved sequence with meso-enzyme
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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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no oxidadion of several alcohols
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r
L-acetoin + NADH
L-2,3-butanediol
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stereoisomeric specificity for hydroxyl group in L configuration
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?
(S,S)-butanediol + NAD+
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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.
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?
L-acetoin + NADH + H+
(S,S)-butanediol + NAD+
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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.
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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
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?
additional information
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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
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?
additional information
?
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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
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?
additional information
?
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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)
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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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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)
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additional information
?
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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)
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additional information
?
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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
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additional information
?
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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
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additional information
?
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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
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additional information
?
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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
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additional information
?
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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
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additional information
?
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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
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additional information
?
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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
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additional information
?
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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
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additional information
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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
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?
additional information
?
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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
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?
additional information
?
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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
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?
additional information
?
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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
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?
additional information
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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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