1.1.1.B20: meso-2,3-butandiol dehydrogenase
This is an abbreviated version!
For detailed information about meso-2,3-butandiol dehydrogenase, go to the full flat file.
Word Map on EC 1.1.1.B20
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1.1.1.B20
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klebsiella
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diacetyl
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pneumoniae
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fed-batch
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nadh-dependent
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2s,3s-2,3-butanediol
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enterobacter
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synthesis
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serratia
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marcescens
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cloacae
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hydrolysate
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acetobacter
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biofuels
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polymyxa
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lactis
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byproduct
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acetolactate
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1,4-butanediol
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bioconversion
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aerogenes
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racemic
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refolding
- 1.1.1.B20
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klebsiella
- diacetyl
- pneumoniae
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fed-batch
-
nadh-dependent
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2s,3s-2,3-butanediol
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enterobacter
- synthesis
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serratia
- marcescens
- cloacae
- hydrolysate
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acetobacter
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biofuels
- polymyxa
- lactis
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byproduct
- acetolactate
- 1,4-butanediol
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bioconversion
- aerogenes
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racemic
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refolding
Reaction
Synonyms
(2R,3R)-2,3-butanediol dehydrogenase, 2,3-BD dehydrogenase, 2,3-butanediol dehydrogenase, 2,3-butanediol dehydrogenases, ADH-9, ARA1, BDH, BdhA, BS-BDH, BtBDH, budC, butACg, butanediol dehydrogenase, ButB, CG-BDH, Cgl2674, mbdh, meso-2,3-BD dehydrogenase, meso-2,3-BDH, meso-2,3-butanediol dehydrogenase, meso-acetoin reductase, meso-BD, meso-BDH, MF996569, More, NAD(H)-dependent meso-2,3-BDH, NAD(H)-dependent meso-2,3-butanediol dehydrogenase, PA4153, PB24_3312, PF-BDH, PF1960, PT-BDH, R,R-2,3-butanediol dehydrogenase/meso-2,3-butanediol dehydrogenase/diacetyl reductase, SmBdh
ECTree
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Substrates Products
Substrates Products on EC 1.1.1.B20 - meso-2,3-butandiol dehydrogenase
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REACTION DIAGRAM
(2R,3R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
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r
(2S,3S)-2,3-butanediol + NAD+
(3S)-acetoin + NADH
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(2S,3S)-2,3-butanediol is a poor substrate
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?
(R,R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
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-
r
2 (R,S)-acetoin + 2 NADPH + 2 H+
(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
2 acetoin + 2 NADH + 2 H+
(2S,3S)-2,3-butanediol + meso-2,3-butanediol + 2 NAD+
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racemic mixture of (3S/3R)-acetoin
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-
r
2,3-hexanedione + NADH + H+
(S)-3-hydroxy-2-hexanone + NAD+
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-
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?
2,3-pentanedione + NADH + H+
(3S)-3-hydroxy-2-pentanone + NAD+
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-
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?
diacetyl + 2 NADH + 2 H+
(2R,3R)-butane-2,3-diol + 2 NAD+
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-
-
r
meso-2,3-butanediol + NADP+
(R)-acetoin + NADPH + H+
very low activity
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-
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
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-
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?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
slightly preferred substrate
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?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
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-
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r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
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-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
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-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
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-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
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-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
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-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
preferred substrate
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-
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
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-
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?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
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-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
meso-butane-2,3-diol
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?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
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-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
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-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
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-
-
r
(3S)-acetoin + NADH + H+
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-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3S)-acetoin + NADH + H+
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-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3S)-acetoin + NADH + H+
-
-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3S)-acetoin + NADH + H+
-
-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3S)-acetoin + NADH + H+
-
-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3S)-acetoin + NADH + H+
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-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3S)-acetoin + NADH + H+
-
-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3S)-acetoin + NADH + H+
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-
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-
r
(2R,3S)-butane-2,3-diol + NAD+
(3S)-acetoin + NADH + H+
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-
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-
r
(2R,3S)-butane-2,3-diol + NAD+
(3S)-acetoin + NADH + H+
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-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3S)-acetoin + NADH + H+
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-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3S)-acetoin + NADH + H+
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-
-
r
(3S)-acetoin + NADH + H+
low activity
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-
r
(2S,3S)-2,3-butanediol + NAD+
(3S)-acetoin + NADH + H+
low activity
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-
r
(3R)-acetoin + NADH + H+
meso-2,3-butanediol + NAD+
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r
(3R)-acetoin + NADH + H+
meso-2,3-butanediol + NAD+
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low activity in vivo
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r
(2S,3S)-2,3-butanediol + NAD+
at pH 9.0
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r
(3S)-acetoin + NADH + H+
(2S,3S)-2,3-butanediol + NAD+
at pH 9.0
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-
r
(R)-acetoin + NADH + H+
meso-2,3-butanediol + NAD+
preferred reaction direction
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-
r
(R)-acetoin + NADH + H+
meso-2,3-butanediol + NAD+
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-
r
(R)-acetoin + NADH + H+
meso-2,3-butanediol + NAD+
preferred reaction direction
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-
r
meso-2,3-butanediol + NADP+
very low activity
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-
r
(R)-acetoin + NADPH + H+
meso-2,3-butanediol + NADP+
very low activity
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-
r
(S,S)-1,2-cyclohexanediol + NAD+
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-
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?
1,2-cyclohexanedione + NADH + H+
(S,S)-1,2-cyclohexanediol + NAD+
Serratia marcescens CECT 977
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-
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?
(S)-2-hydroxy-1-phenylpropan-1-one + NAD+
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?
1-phenyl-1,2-propanedione + NADH + H+
(S)-2-hydroxy-1-phenylpropan-1-one + NAD+
Serratia marcescens CECT 977
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?
4-methyl-2-pentanol + NAD+
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low activity
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-
r
4-methyl-2-pentanone + NADH + H+
4-methyl-2-pentanol + NAD+
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low activity
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r
meso-2,3-butanediol + NAD+
racemic mixture of (3S/3R)-acetoin
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r
acetoin + NADH + H+
meso-2,3-butanediol + NAD+
racemic mixture of (3S/3R)-acetoin
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-
r
meso-2,3-butanediol + NAD+
(R)-acetoin + NADH + H+
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r
meso-2,3-butanediol + NAD+
(R)-acetoin + NADH + H+
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the (S)-specific ADH-9 produces (R)-acetoin by an oxidative route starting from meso-2,3-butanediol
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r
meso-2,3-butanediol + NAD+
(R)-acetoin + NADH + H+
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enantioselective enzymatic synthesis of the alpha-hydroxy ketone(R)-acetoin from meso-2,3-butanediol
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r
?
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stereoisomeric composition analysis of 2,3-butanediol produced by strain 10-1-A using gas chromatography. Strain 10-1-A produces a mixture of (2R,3R)-2,3-butanediol and meso-2,3-butanediol with a ratio of nearly 1:1. As (3R)-acetoin is the major source of (2R,3R)-2,3-butanediol and meso-2,3-butanediol, a meso-butanediol dehydrogenase and a (2R,3R)-2,3-butanediol dehydrogenase are co-present in strain 10-1-A
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additional information
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most of the Bacillus strains produce 2,3-butanediol but not acetoin as their major product
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additional information
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stereoisomeric composition analysis of 2,3-butanediol produced by strain 10-1-A using gas chromatography. Strain 10-1-A produces a mixture of (2R,3R)-2,3-butanediol and meso-2,3-butanediol with a ratio of nearly 1:1. As (3R)-acetoin is the major source of (2R,3R)-2,3-butanediol and meso-2,3-butanediol, a meso-butanediol dehydrogenase and a (2R,3R)-2,3-butanediol dehydrogenase are co-present in strain 10-1-A
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additional information
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most of the Bacillus strains produce 2,3-butanediol but not acetoin as their major product
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additional information
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meso-2,3-butanediol dehydrogenase (BDH) catalyzes the redox reaction between (R)-acetoin and meso-2,3-butanediol
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additional information
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enzyme BtBDH is active with meso-2,3-butanediol and (2R,3R)-2,3-butanediol, whereas no activity is observed with (2S,3S)-2,3-butanediol. BtBDH shows similar oxidative activity toward meso-2,3-butanediol and (2R,3R)-2,3-butanediol, and it exhibits a 3fold higher reduction activity toward acetoin compared to diacetyl
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additional information
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enzyme BtBDH is active with meso-2,3-butanediol and (2R,3R)-2,3-butanediol, whereas no activity is observed with (2S,3S)-2,3-butanediol. BtBDH shows similar oxidative activity toward meso-2,3-butanediol and (2R,3R)-2,3-butanediol, and it exhibits a 3fold higher reduction activity toward acetoin compared to diacetyl
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additional information
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NMR identification and quantification of reaction products. Meso-2,3-butanediol is the major form (over 95% of the 2,3-butanediol pool, depending on oxygen availability) produced in fermentations using a strain that overexpresses ALS/ALDC of Lactobacillus lactis and BDH of Corynebacterium glutamicum, i.e., strain DELTAaceEDELTApqoDELTAldhA(pEKEx2als,aldB,butACg)
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additional information
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the enzyme is also active with diacetyl and NADH
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additional information
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the enzyme is also active with diacetyl and NADH
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additional information
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the enzyme is highly stereospecific, and shows no significant activities towards 2R,3R-2,3-butanediol, 1,4-butanediol, and 2S,3S-2,3-butanediol
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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 (EC 1.1.1.76) 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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the enzyme is highly stereospecific, and shows no significant activities towards 2R,3R-2,3-butanediol, 1,4-butanediol, and 2S,3S-2,3-butanediol
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?
additional information
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production of S,S- and/or R,R- and meso-2,3-BDO by Paenibacillus brasilensis strain PB24 grown in the modified YEPD medium, pH 6.3, 32°C, up to 72 h
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additional information
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production of S,S- and/or R,R- and meso-2,3-BDO by Paenibacillus brasilensis strain PB24 grown in the modified YEPD medium, pH 6.3, 32°C, up to 72 h
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additional information
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the (2R,3R)-2,3-butanediol dehydrogenase is active with (R,R)-butane-2,3-diol, but also with meso-butane-2,3-diol, but not with with (2S,3S)-2,3-butane-2,3-diol. No activity with 2-butanol, 1,3-butanediol, 1,2-pentanediol, 1,3-propanediol, and glycerol in the oxidation reaction. And no activity with 2,4-pentanedione, butanone, 2,5-hexanedione, n-butanal and 1,3-dihydroxypropanone in the reduction reaction. Substrate specificity, overview. (2R,3R)-2,3-BDH reduces diacetyl into (3R)-acetoin and (2R,3R)-2,3-BD, while racemic acetoin is reduced into (2R,3R)-2,3-BD and meso-2,3-BD
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additional information
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(2R,3R)-2,3-butanediol is no substrate for the enzyme
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additional information
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(2R,3R)-2,3-butanediol is no substrate for the enzyme
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?
additional information
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2,3-butanediol dehydrogenase (BudC) catalyses the selective asymmetric reductions of prochiral alpha-diketones to the corresponding alpha-hydroxy ketones and diols. BudC is highly active towards structurally diverse diketones in combination with nicotinamide cofactor regeneration systems. Aliphatic diketones, cyclic diketones, and alkyl phenyl diketones are well accepted, whereas their derivatives possessing two bulky groups are not converted. In the reverse reaction vicinal diols are preferred over other substrates with hydroxy/keto groups in non-vicinal positions. Substrate specificity and stereoselectivity, overview. In the reductive reaction diacetyl is the preferred substrate of BudC over acetoin, while only meso-2,3-butanediol oxidation is catalysed by the enzyme under the conditions assessed. No activity with (2S,3S)-butane-2,3-diol and (2R,3R)-butane-2,3-diol. BudC is S-selective for the reduction of diacetyl yielding (S,S)-2,3-butanediol ((S,S)-2,3-BDO), rac-acetoin is reduced to both meso-2,3-BDO and (S,S)-2,3-BDO. Here (R)-acetoin is the preferred substrate and 15% (S)-acetoin remains unconverted after 24 h. Thus, BudC shows a stereo-preference consistent with meso-2,3-butanediol dehydrogenases with respect to acetoin. No activity with R-benzoin, rac-benzoin, benzil, acetone, 2,4-pentanediol, 1,3-butanediol, ethanol, and 2-propanol
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additional information
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substrate promiscuity of the SmBdh enzyme, SmBdh has been reported to be able to reduce both (3R)- and (3S)-acetoin to 2,3-BDO, although (3R)-acetoin is more readily converted than (3S)-acetoin. On the other hand, SmBdh is able to oxidize meso-2,3-BDO and (2S,3S)-BDO, while oxidation of (2R,3R)-BDO is not detectable. Moreover, its activity towards (2S,3S)-BDO is only 11% of that towards meso-2,3-BDO. The enzyme is classified as an S-acting Bdh based on production of meso-2,3-BDO and (2S,3S)-BDO from a racemic mixture of acetoin
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additional information
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substrate promiscuity of the SmBdh enzyme, SmBdh has been reported to be able to reduce both (3R)- and (3S)-acetoin to 2,3-BDO, although (3R)-acetoin is more readily converted than (3S)-acetoin. On the other hand, SmBdh is able to oxidize meso-2,3-BDO and (2S,3S)-BDO, while oxidation of (2R,3R)-BDO is not detectable. Moreover, its activity towards (2S,3S)-BDO is only 11% of that towards meso-2,3-BDO. The enzyme is classified as an S-acting Bdh based on production of meso-2,3-BDO and (2S,3S)-BDO from a racemic mixture of acetoin
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additional information
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substrate promiscuity of the SmBdh enzyme, SmBdh has been reported to be able to reduce both (3R)- and (3S)-acetoin to 2,3-BDO, although (3R)-acetoin is more readily converted than (3S)-acetoin. On the other hand, SmBdh is able to oxidize meso-2,3-BDO and (2S,3S)-BDO, while oxidation of (2R,3R)-BDO is not detectable. Moreover, its activity towards (2S,3S)-BDO is only 11% of that towards meso-2,3-BDO. The enzyme is classified as an S-acting Bdh based on production of meso-2,3-BDO and (2S,3S)-BDO from a racemic mixture of acetoin
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additional information
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Serratia marcescens CECT 977
2,3-butanediol dehydrogenase (BudC) catalyses the selective asymmetric reductions of prochiral alpha-diketones to the corresponding alpha-hydroxy ketones and diols. BudC is highly active towards structurally diverse diketones in combination with nicotinamide cofactor regeneration systems. Aliphatic diketones, cyclic diketones, and alkyl phenyl diketones are well accepted, whereas their derivatives possessing two bulky groups are not converted. In the reverse reaction vicinal diols are preferred over other substrates with hydroxy/keto groups in non-vicinal positions. Substrate specificity and stereoselectivity, overview. In the reductive reaction diacetyl is the preferred substrate of BudC over acetoin, while only meso-2,3-butanediol oxidation is catalysed by the enzyme under the conditions assessed. No activity with (2S,3S)-butane-2,3-diol and (2R,3R)-butane-2,3-diol. BudC is S-selective for the reduction of diacetyl yielding (S,S)-2,3-butanediol ((S,S)-2,3-BDO), rac-acetoin is reduced to both meso-2,3-BDO and (S,S)-2,3-BDO. Here (R)-acetoin is the preferred substrate and 15% (S)-acetoin remains unconverted after 24 h. Thus, BudC shows a stereo-preference consistent with meso-2,3-butanediol dehydrogenases with respect to acetoin. No activity with R-benzoin, rac-benzoin, benzil, acetone, 2,4-pentanediol, 1,3-butanediol, ethanol, and 2-propanol
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additional information
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(2R,3R)-2,3-butanediol is no substrate for the enzyme
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additional information
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(2R,3R)-2,3-butanediol is no substrate for the enzyme
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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, cf. EC 1.1.1.76
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additional information
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reaction component identification and quantification by GC-MS. No or very poor activity with isopropanol 2-methyl-1-butanol, 2-methyl-2-butanol, 2,5-hexanediol, 1,4-butanediol
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