1.1.1.4: (R,R)-butanediol dehydrogenase
This is an abbreviated version!
For detailed information about (R,R)-butanediol dehydrogenase, go to the full flat file.
Word Map on EC 1.1.1.4
-
1.1.1.4
-
2r,3r-2,3-butanediol
-
acetolactate
-
r-acetoin
-
alpha-acetolactate
-
meso-2,3-bd
-
polymyxa
-
synthesis
- 1.1.1.4
-
2r,3r-2,3-butanediol
- acetolactate
-
r-acetoin
- alpha-acetolactate
-
meso-2,3-bd
- polymyxa
- synthesis
Reaction
Synonyms
(2R,3R)-2,3-BDH, (2R,3R)-2,3-butanediol dehydrogenase, (R)-2,3-butanediol dehydrogenase, (R)-diacetyl reductase, (R,R)-butane-2,3-diol dehydrogenase, 1-amino-2-propanol dehydrogenase, 1-amino-2-propanol oxidoreductase, 2,3-BDH/AR, 2,3-butanediol dehydrogenase, 2,3-butanediol dehydrogenase/acetoin reductase, 2R,3R-2,3-BD dehydrogenase, 2R-3R-BDH, acetoin reductase, acetoin/diacetyl reductase, ADH-9, aminopropanol oxidoreductase, AR/BDH, BaBdhA, BcBDH, BDH, BDH1, Bdh1p, BDH2, Bdh2p, BDH99::67, BdhA, BtBDH, ButA, butanediol dehydrogenase, ButB, butylene glycol dehydrogenase, butyleneglycol dehydrogenase, D-(-)-butanediol dehydrogenase, D-1-amino-2-propanol dehydrogenase, D-1-amino-2-propanol:NAD+ oxidoreductase, D-2,3-BD dehydrogenase, D-aminopropanol dehydrogenase, dehydrogenase, D-aminopropanol, dehydrogenase, D-butanediol, DHAD, diacetyl reductase (acetoin), EC 1.1.1.74, GDH, GldA, meso-2,3-butanediol dehydrogenase, meso-BDH, MF996569, More, NAD(H)-dependent 2,3-butanediol dehydrogenase, NADH-dependent 2,3-butanediol dehydrogenase, PA4153, PB24_3312, R,R-2,3-butanediol dehydrogenase/meso-2,3-butanediol dehydrogenase/diacetyl reductase, R,R-BD-DH, R,R-BDH, R-selective 2,3-butanediol dehydrogenase, SLAC
ECTree
1.1.1.4 (R,R)-butanediol dehydrogenaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 1.1.1.4 - (R,R)-butanediol dehydrogenase
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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
(2R,3R)-2,3-butanediol + NADP+
(R)-acetoin + NADPH + H+
no detectable activity with (2S,3S)-2,3-butanediol
-
-
r
(2R,3R)-butane-2,3-diol + NAD+
?
69.5% activity compared to (2R,3R)-butane-2,3-diol
-
-
?
(R)-1,2-propanediol + NAD+
hydroxyacetone + NADH + H+
73% activity compared to (2R,3R)-butane-2,3-diol in the oxidation reaction, very low activity with the (S)-enantiomer
-
-
?
(R)-1-phenyl-1,2-ethanediol + NAD+
?
32.2% activity compared to (2R,3R)-butane-2,3-diol
-
-
?
(R)-acetoin + NADPH + H+
(2R,3R)-2,3-butanediol + NAD+
-
-
-
?
(R)-acetoin + NADPH + H+
(2R,3R)-butane-2,3-diol + NADP+
wild type enzyme does not use NADPH as coenzyme
-
-
?
(R,S)-3-hydroxy-2-pentanone + NADH
2,3-pentanediol + NAD+
-
-
-
r
(R,S)-4-hydroxy-3-pentanone + NADH
2,3-pentanediol + NAD+
-
-
-
r
1,2-hexanediol + NAD+
? + NADH + H+
50% activity compared to (2R,3R)-butane-2,3-diol in the oxidation reaction
-
-
?
1,2-pentanediol + NAD+
? + NADH + H+
74% activity compared to (2R,3R)-butane-2,3-diol in the oxidation reaction
-
-
?
2-hydroxyacetophenone + NADH + H+
?
8.7% activity compared to (R)-acetoin
-
-
?
2-octanone + NADH + H+
?
9.3% activity compared to (R)-acetoin
-
-
?
3,4-hexanedione + 2 NADH + 2 H+
(3R,4R)-3,4-hexanediol + 2 NAD+
-
-
-
r
3-methyl-2-butenal + NADH + H+
?
16.7% activity compared to (R)-acetoin
-
-
?
acetoin + 2 NADPH + 2 H+
(2R,3R)-2,3-butanediol + meso-2,3-butanediol + 2 NADP+
-
-
-
r
acetoin + NAD+
diacetyl + NADH
-
18% of the activity with 2,3-butanediol, in the reverse reaction 150% of the activity with acetoin
-
-
r
butane-1,3-diol + NAD+
?
14.7% activity compared to (2R,3R)-butane-2,3-diol
-
-
?
butane-1,4-diol + NAD+
?
2.9% activity compared to (R,R)-butane-2,3-diol
-
-
?
diacetyl + 2 NADH + 2 H+
(2R,3R)-butane-2,3-diol + 2 NAD+
-
-
-
r
dihydroxyacetone phosphate + NADH
?
-
82% of the activity with acetoin
-
-
?
ethyl 4-chloro-3-hydroxybutyrate + NAD+
?
12.2% activity compared to (2R,3R)-butane-2,3-diol
-
-
?
furfural + NADPH + H+
(furan-2-yl)methanol + NADP+
-
-
-
?
isobutanol + NAD+
?
0.4% activity compared to (R,R)-butane-2,3-diol
-
-
?
propane-1,3-diol + NAD+
?
1.4% activity compared to (R,R)-butane-2,3-diol
-
-
?
sodium lactate + NAD+
?
10.2% activity compared to (2R,3R)-butane-2,3-diol
-
-
?
(2R,3R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
r
(2R,3R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
Alkalihalobacillus clausii DSM 8716T
-
-
-
r
(2R,3R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
r
(2R,3R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
r
(2R,3R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
-
?
(2R,3R)-butane-2,3-diol + NAD+
(3R,3S)-acetoin + NADH + H+
preferred substrate
-
-
r
(2R,3R)-butane-2,3-diol + NAD+
(3R,3S)-acetoin + NADH + H+
preferred substrate, very low activity with the (S)-enantiomer
-
-
r
(2R,3R)-butane-2,3-diol + NAD+
(3R,3S)-acetoin + NADH + H+
Paenibacillus polymyxa ATCC 12321 has the ability to form almost exclusively the R isomer of 2,3-BDL (over 98%) when grown under anaerobic conditions
-
-
r
(2R,3R)-butane-2,3-diol + NAD+
(3R,3S)-acetoin + NADH + H+
sole product in the reduction reaction, preferred substrate in the oxidation reaction
preferred substrate in the reduction reaction
-
r
(2R,3R)-butane-2,3-diol + NAD+
(3R,3S)-acetoin + NADH + H+
Paenibacillus polymyxa ATCC 12321 has the ability to form almost exclusively the R isomer of 2,3-BDL (over 98%) when grown under anaerobic conditions
-
-
r
(2R,3R)-butane-2,3-diol + NAD+
(3R,3S)-acetoin + NADH + H+
sole product in the reduction reaction, preferred substrate in the oxidation reaction
preferred substrate in the reduction reaction
-
r
(2R,3R)-butane-2,3-diol + NAD+
(3R,3S)-acetoin + NADH + H+
-
-
-
-
r
(2R,3R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
slightly preferred substrate
-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
slightly preferred substrate
-
-
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
-
-
?
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
-
-
?
(2S)-acetoin + NADH + H+
(2S,3S)-butane-2,3-diol + NAD+
-
the enzyme is not absolutely specific for (S)-acetoin, though this is the preferred substrate
-
-
?
(2S)-acetoin + NADH + H+
(2S,3S)-butane-2,3-diol + NAD+
-
the enzyme is not absolutely specific for (S)-acetoin, though this is the preferred substrate
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(2S)-acetoin + NADH + H+
-
very low activity
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(2S)-acetoin + NADH + H+
-
very low activity
-
-
?
(2S,3S)-butane-2,3-diol + NAD+
(2S)-acetoin + NADH + H+
-
-
-
-
?
(3R,3S)-acetoin + NADH
(2R,3R)-2,3-butanediol + meso-2,3-butanediol + NAD+
-
-
-
r
(3R,3S)-acetoin + NADH
(2R,3R)-2,3-butanediol + meso-2,3-butanediol + NAD+
-
-
-
r
(3R,3S)-acetoin + NADH
(2R,3R)-2,3-butanediol + meso-2,3-butanediol + NAD+
-
the enzyme shows lower Km value and higher catalytic efficiency for (3S/3R)-acetoin in comparison to those for (2R,3R)-2,3-butanediol and meso-2,3-butanediol, the reduction reaction is preferred, low activity with (2R,3R)-2,3-butanediol
-
-
r
(3R,3S)-acetoin + NADH
(2R,3R)-2,3-butanediol + meso-2,3-butanediol + NAD+
-
the enzyme shows lower Km value and higher catalytic efficiency for (3S/3R)-acetoin in comparison to those for (2R,3R)-2,3-butanediol and meso-2,3-butanediol, the reduction reaction is preferred, low activity with (2R,3R)-2,3-butanediol
-
-
r
(3R,3S)-butane-2,3-diol + NAD+
(3R,3S)-acetoin + NADH + H+
-
-
-
-
?
(R)-acetoin + NADH + H+
(2R,3R)-butane-2,3-diol + NAD+
the activity of (R)-acetoin reduction is 7.7times higher than that of (2R,3R)-butane-2,3-diol oxidation at pH 7.0
-
-
r
(R)-acetoin + NADH + H+
(2R,3R)-butane-2,3-diol + NAD+
the activity of (R)-acetoin reduction is 7.7times higher than that of (2R,3R)-butane-2,3-diol oxidation at pH 7.0
-
-
r
(R)-acetoin + NADH + H+
(2R,3R)-butane-2,3-diol + NAD+
-
-
-
?
(R)-acetoin + NADH + H+
(R,R)-butane-2,3-diol + NAD+
-
low activity
-
-
r
(R)-acetoin + NADH + H+
(R,R)-butane-2,3-diol + NAD+
-
low activity
-
-
r
(R)-acetoin + NADH + H+
(R,R)-butane-2,3-diol + NAD+
-
high level production of (R,R)-butane-2,3-diol
-
-
r
(R)-acetoin + NADH + H+
(R,R)-butane-2,3-diol + NAD+
Paenibacillus polymyxa DSM 365
-
high level production of (R,R)-butane-2,3-diol
-
-
r
(R,R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
-
-
r
(R,R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
-
-
r
(R,R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
-
-
r
(R,R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
-
-
r
(R,R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
-
-
r
(R,R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
-
-
r
(R,R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
-
-
r
(R,R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
stereoselective interconversion
-
-
r
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
-
-
r
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
preferred substrate, 100% activity
-
-
?
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
preferred substrate, 100% activity
-
-
?
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
-
-
r
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
-
-
r
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
-
-
-
r
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
effects of growth substrate on enzyme activity in vivo, overview
-
-
r
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
effects of growth substrate on enzyme activity in vivo, overview
-
-
r
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
effects of growth substrate on enzyme activity in vivo, overview
-
-
r
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
effects of growth substrate on enzyme activity in vivo, overview
-
-
r
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
-
-
?
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
-
-
?
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
-
-
r
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
-
-
r
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
-
-
r
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
-
-
r
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
-
-
r
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
-
-
r
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
-
-
r
(R,R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
-
-
?
2,2,2-trifluoroacetophenone + NADH + H+
?
28% activity compared to (R)-acetoin
-
-
?
2,2,2-trifluoroacetophenone + NADH + H+
?
28% activity compared to (R)-acetoin
-
-
?
2,3-butanediol + NAD+
acetoin + NADH
-
2,3-butanediol without specification of stereochemistry
-
-
?
2,3-butanediol + NAD+
acetoin + NADH
-
2,3-butanediol without specification of stereochemistry
-
r
2,3-butanediol + NAD+
acetoin + NADH
-
oxidation occurs selectively at the (R)-center of 2,3-butanediol
-
r
2,3-hexanedione + NADH + H+
(3R)-3-hydroxy-2-hexanone + NAD+
small amounts of (2R)-2-hydroxy-3-hexanone are produced as by-product
-
-
r
2,3-hexanedione + NADH + H+
(3R)-3-hydroxy-2-hexanone + NAD+
Alkalihalobacillus clausii DSM 8716T
small amounts of (2R)-2-hydroxy-3-hexanone are produced as by-product
-
-
r
2,3-pentanediol + NAD+
4-hydroxy-3-pentanone + 3-hydroxy-2-pentanone + NADH
-
-
-
-
?
2,3-pentanediol + NAD+
4-hydroxy-3-pentanone + 3-hydroxy-2-pentanone + NADH
-
racemate
-
r
2,3-pentanedione + NADH + H+
3-hydroxy-2-pentanone + NAD+
small amounts of 2,3-pentanediol are produced as by-product
-
-
r
2,3-pentanedione + NADH + H+
3-hydroxy-2-pentanone + NAD+
Alkalihalobacillus clausii DSM 8716T
small amounts of 2,3-pentanediol are produced as by-product
-
-
r
2-hydroxyacetophenone + NADH + H+
(R)-1-phenyl-1,2-ethanediol + NAD+
-
-
-
?
2-hydroxyacetophenone + NADH + H+
(R)-1-phenyl-1,2-ethanediol + NAD+
over 99% enantiomeric excess
-
-
?
2-hydroxyacetophenone + NADH + H+
(R)-1-phenyl-1,2-ethanediol + NAD+
-
-
-
?
2-hydroxyacetophenone + NADH + H+
(R)-1-phenyl-1,2-ethanediol + NAD+
over 99% enantiomeric excess
-
-
?
5-methyl-2,3-hexanedione + NADH + H+
(3R)-5-methyl-3-hydroxy-2-hexanone + NAD+
small amounts of 5-methyl-2-hydroxy-3-hexanone and traces of (3S)-5-methyl-3-hydroxy-2-hexanone are produced as by-products
-
-
r
5-methyl-2,3-hexanedione + NADH + H+
(3R)-5-methyl-3-hydroxy-2-hexanone + NAD+
Alkalihalobacillus clausii DSM 8716T
small amounts of 5-methyl-2-hydroxy-3-hexanone and traces of (3S)-5-methyl-3-hydroxy-2-hexanone are produced as by-products
-
-
r
acetaldehyde + NADH + H+
ethanol + NAD+
-
-
-
?
acetaldehyde + NADPH + H+
ethanol + NADP+
-
-
-
?
acetoin + NADH + H+
2,3-butanediol + NAD+
-
-
enzyme 1, only meso-2,3-butanediol is formed, enzyme 2 gives mixture of meso- and optical isomers
r
butane-1,2-diol + NAD+
?
76.6% activity compared to (R,R)-butane-2,3-diol
-
-
?
butane-1,2-diol + NAD+
?
76.6% activity compared to (R,R)-butane-2,3-diol
-
-
?
diacetyl + NADH
2,3-butanediol + NAD+
-
-
enzyme 1, only meso-2,3-butanediol is formed, enzyme 2 gives mixture of meso- and optical isomers
r
diacetyl + NADH + H+
(R)-acetoin + NAD+
69.3% activity compared to (R)-acetoin
-
-
r
diacetyl + NADH + H+
(R)-acetoin + NAD+
69.3% activity compared to (R)-acetoin
-
-
r
diacetyl + NADH + H+
acetoin + NAD+
88.2% activity compared to acetoin
-
-
?
diacetyl + NADH + H+
acetoin + NAD+
88.2% activity compared to acetoin
-
-
?
diacetyl + NADH + H+
acetoin + NAD+
91% activity compared to (3R,3S)-acetoin in the reduction reaction, cf. EC 1.1.1.303
-
-
?
diacetyl + NADH + H+
acetoin + NAD+
91% activity compared to (3R,3S)-acetoin in the reduction reaction, cf. EC 1.1.1.303
-
-
?
diacetyl + NADH + H+
acetoin + NAD+
-
diacetyl can be converted into 2,3-butanediol via acetoin by the enzyme
-
-
?
diacetyl + NADH + H+
acetoin + NAD+
-
diacetyl can be converted into 2,3-butanediol via acetoin by the enzyme
-
-
?
furfural + NADH + H+
(furan-2-yl)methanol + NAD+
-
-
-
?
glycerol + NAD+
?
16.3% activity compared to (2R,3R)-butane-2,3-diol
-
-
?
glycerol + NAD+
?
16.3% activity compared to (2R,3R)-butane-2,3-diol
-
-
?
meso-2,3-butanediol + NAD+
D-(-)-acetoin + NADH
-
-
(3S)-acetoin
r
meso-butane-2,3-diol + NAD+
(3S)-acetoin + NADH + H+
-
-
-
-
?
meso-butane-2,3-diol + NAD+
acetoin + NADH + H+
93.6% activity compared to (R,R)-butane-2,3-diol
-
-
?
meso-butane-2,3-diol + NAD+
acetoin + NADH + H+
93.6% activity compared to (R,R)-butane-2,3-diol
-
-
?
meso-butane-2,3-diol + NAD+
acetoin + NADH + H+
61% activity compared to (2R,3R)-butane-2,3-diol in the oxidation reaction
-
-
r
meso-butane-2,3-diol + NAD+
acetoin + NADH + H+
72% activity compared to (2R,3R)-butane-2,3-diol in the oxidation reaction
-
-
r
propane-1,2-diol + NAD+
?
58.6% activity compared to (R,R)-butane-2,3-diol
-
-
?
rac-1,2-propanediol + NAD+
hydroxyacetone + NADH + H+
68% activity compared to (2R,3R)-butane-2,3-diol in the oxidation reaction
-
-
?
additional information
?
-
substrate specificity analysis, overview. Enzyme BcBDH catalyzes the selective asymmetric reduction of prochiral 1,2-diketones to the corresponding HK and, in some cases, the reduction of the same to the corresponding 1,2-diols. Aliphatic diketones, like 2,3-pentanedione, 2,3-hexanedione, 5-methyl-2,3-hexanedione, 3,4-hexanedione, and 2,3-heptanedione are well transformed. In addition, surprisingly alkyl phenyl dicarbonyls, like 2-hydroxy-1-phenylpropan-1-one and phenylglyoxal are accepted, whereas their derivatives with two phenyl groups are not substrates. The biocatalytic reduction of 5-methyl-2,3-hexanedione to mainly 5-methyl-3-hydroxy-2-hexanone with only small amounts of 5-methyl-2-hydroxy-3-hexanone within an enzyme membrane reactor is demonstrated. Stereoselectivity and conversion is analyzed by carrying out the reduction reaction of selected diketones and alpha-hydroxyketones
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-
-
additional information
?
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Alkalihalobacillus clausii DSM 8716T
substrate specificity analysis, overview. Enzyme BcBDH catalyzes the selective asymmetric reduction of prochiral 1,2-diketones to the corresponding HK and, in some cases, the reduction of the same to the corresponding 1,2-diols. Aliphatic diketones, like 2,3-pentanedione, 2,3-hexanedione, 5-methyl-2,3-hexanedione, 3,4-hexanedione, and 2,3-heptanedione are well transformed. In addition, surprisingly alkyl phenyl dicarbonyls, like 2-hydroxy-1-phenylpropan-1-one and phenylglyoxal are accepted, whereas their derivatives with two phenyl groups are not substrates. The biocatalytic reduction of 5-methyl-2,3-hexanedione to mainly 5-methyl-3-hydroxy-2-hexanone with only small amounts of 5-methyl-2-hydroxy-3-hexanone within an enzyme membrane reactor is demonstrated. Stereoselectivity and conversion is analyzed by carrying out the reduction reaction of selected diketones and alpha-hydroxyketones
-
-
-
additional information
?
-
-
no activity with meso-butane-2,3-diol, glycerol, glycerol-3-phosphate, 1,3-dihydroxyacetone, dihydroxyacetonephosphate, glyceraldehyde-3-phosphate, 2-butanol, and 1,3-butanediol
-
-
?
additional information
?
-
-
no activity with meso-butane-2,3-diol, glycerol, glycerol-3-phosphate, 1,3-dihydroxyacetone, dihydroxyacetonephosphate, glyceraldehyde-3-phosphate, 2-butanol, and 1,3-butanediol
-
-
?
additional information
?
-
no activity with (S,S)-butane-2,3-diol
-
-
?
additional information
?
-
no activity with (S,S)-butane-2,3-diol
-
-
?
additional information
?
-
an enantiocomplementary carbonyl reductase, 2,3-butanediol dehydrogenase (BDHA) from Bacillus subtilis is discovered to convert 2-hydroxyacetophenone (2-HAP) to (R)-1-phenyl-1,2-ethanediol ((R)-PED) with excellent stereochemical selectivity. No activity with NADPH
-
-
-
additional information
?
-
an enantiocomplementary carbonyl reductase, 2,3-butanediol dehydrogenase (BDHA) from Bacillus subtilis is discovered to convert 2-hydroxyacetophenone (2-HAP) to (R)-1-phenyl-1,2-ethanediol ((R)-PED) with excellent stereochemical selectivity. No activity with NADPH
-
-
-
additional information
?
-
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
-
-
-
additional information
?
-
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
-
-
-
additional information
?
-
enzyme is a strictly NADPH-dependent primary-secondary alcohol dehydrogenase able to reduce acetoin to 2,3-butanediol. The enzyme accepts a range of 2-, 3-, and 4-carbon substrates, including the nonphysiological ketones acetone and butanone
-
-
?
additional information
?
-
-
enzyme is a strictly NADPH-dependent primary-secondary alcohol dehydrogenase able to reduce acetoin to 2,3-butanediol. The enzyme accepts a range of 2-, 3-, and 4-carbon substrates, including the nonphysiological ketones acetone and butanone
-
-
?
additional information
?
-
-
no activity with (2S,3S)-butane-2,3-diol or diacetyl
-
-
?
additional information
?
-
-
no activity with (2S,3S)-butane-2,3-diol or diacetyl
-
-
?
additional information
?
-
substrate specificity, overview. No or poor activity with ethanol, ethylene glycol, diethylene glycol, 1-propanol, 2-propanol, 1,3-propanediol, glycerol, dipropylene glycol, 1-butanol, 1,4-butanediol, 1,2,4-butanetriol, (2S,3S)-butane-2,3-diol, 1,5-pentanediol, 2,4-pentanediol, 3-methyl-1,5-pentandiol, and 1,2,6-hexantriol
-
-
?
additional information
?
-
production of 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
-
-
-
additional information
?
-
production of 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
-
-
-
additional information
?
-
the enzyme is also active in reduction reaction with diacetyl (91% compared to (2R,3S)-acetoin) and glyceraldehyde-3-phosphate (12% compared to (2R,3S)-acetoin), cf. EC 1.1.1.303 and EC 1.1.1.8, respectively, but not with dihydroxyacetone phosphate. It shows low activity in oxidation reaction with ethanol, n-propanol, n-butanol, 1,3-propanediol, and 1,5-pentanediol
-
-
?
additional information
?
-
the enzyme is also active in reduction reaction with diacetyl (91% compared to (2R,3S)-acetoin) and glyceraldehyde-3-phosphate (12% compared to (2R,3S)-acetoin), cf. EC 1.1.1.303 and EC 1.1.1.8, respectively, but not with dihydroxyacetone phosphate. It shows low activity in oxidation reaction with ethanol, n-propanol, n-butanol, 1,3-propanediol, and 1,5-pentanediol
-
-
?
additional information
?
-
-
the enzyme is also active in reduction reaction with diacetyl (91% compared to (2R,3S)-acetoin) and glyceraldehyde-3-phosphate (12% compared to (2R,3S)-acetoin), cf. EC 1.1.1.303 and EC 1.1.1.8, respectively, but not with dihydroxyacetone phosphate. It shows low activity in oxidation reaction with ethanol, n-propanol, n-butanol, 1,3-propanediol, and 1,5-pentanediol
-
-
?
additional information
?
-
no activity with (2S,3S)-2,3-butane-2,3-diol, but the (2R,3R)-2,3-butanediol dehydrogenase is also active with meso-2,3-butanediol. 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
-
-
-
additional information
?
-
-
no activity with (2S,3S)-2,3-butane-2,3-diol, but the (2R,3R)-2,3-butanediol dehydrogenase is also active with meso-2,3-butanediol. 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
-
-
-
additional information
?
-
no activity with (2S,3S)-2,3-butane-2,3-diol, but the (2R,3R)-2,3-butanediol dehydrogenase is also active with meso-2,3-butanediol. 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
-
-
-
additional information
?
-
no activity with (2S,3S)-2,3-butane-2,3-diol, but the (2R,3R)-2,3-butanediol dehydrogenase is also active with meso-2,3-butanediol. 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
-
-
-
additional information
?
-
no activity with (2S,3S)-2,3-butane-2,3-diol, but the (2R,3R)-2,3-butanediol dehydrogenase is also active with meso-2,3-butanediol. 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
-
-
-
additional information
?
-
no activity with (2S,3S)-2,3-butane-2,3-diol, but the (2R,3R)-2,3-butanediol dehydrogenase is also active with meso-2,3-butanediol. 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
-
-
-
additional information
?
-
no activity with (2S,3S)-2,3-butane-2,3-diol, but the (2R,3R)-2,3-butanediol dehydrogenase is also active with meso-2,3-butanediol. 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
-
-
-
additional information
?
-
no activity with (2S,3S)-2,3-butane-2,3-diol, but the (2R,3R)-2,3-butanediol dehydrogenase is also active with meso-2,3-butanediol. 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
-
-
-
additional information
?
-
no activity with (2S,3S)-2,3-butane-2,3-diol, but the (2R,3R)-2,3-butanediol dehydrogenase is also active with meso-2,3-butanediol. 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
-
-
-
additional information
?
-
no activity with acetoin plus NAD+ or (2S,3S)-butane-2,3-diol witrh NAD+, or (S)-1-phenyl-1,2-ethanediol plus NAD+. 5% or less activity with 2-butanol, ethyl lactate, isopropanol, 1-butanol, cyclohexanol, 2-pentanol, 2-octanol, acetophenone, and 4-hydroxy-2-butanone
-
-
?
additional information
?
-
no activity with acetoin plus NAD+ or (2S,3S)-butane-2,3-diol witrh NAD+, or (S)-1-phenyl-1,2-ethanediol plus NAD+. 5% or less activity with 2-butanol, ethyl lactate, isopropanol, 1-butanol, cyclohexanol, 2-pentanol, 2-octanol, acetophenone, and 4-hydroxy-2-butanone
-
-
?
additional information
?
-
-
no activity with acetoin plus NAD+ or (2S,3S)-butane-2,3-diol witrh NAD+, or (S)-1-phenyl-1,2-ethanediol plus NAD+. 5% or less activity with 2-butanol, ethyl lactate, isopropanol, 1-butanol, cyclohexanol, 2-pentanol, 2-octanol, acetophenone, and 4-hydroxy-2-butanone
-
-
?
additional information
?
-
-
3S)-2,3-butanediol, (3R/3S)-acetoin, glycerol, sorbitol or xylitol are no substrates
-
-
?
additional information
?
-
enzyme Bdh1p exhibits (2R,3R)-2,3-butanediol dehydrogenase activity, but Bdh1p also exhibit reductive activities towards lignocellulosic aldehyde inhibitors, such as acetaldehyde, glycolaldehyde, and furfural. No activity for glycolaldehyde or hexaldehyde with NADPH. Propionaldehyde is a poor substrate, no activity with glutaraldehyde
-
-
-
additional information
?
-
enzyme Bdh1p exhibits (2R,3R)-2,3-butanediol dehydrogenase activity, but Bdh1p also exhibit reductive activities towards lignocellulosic aldehyde inhibitors, such as acetaldehyde, glycolaldehyde, and furfural. No activity for glycolaldehyde or hexaldehyde with NADPH. Propionaldehyde is a poor substrate, no activity with glutaraldehyde
-
-
-
additional information
?
-
-
enzyme Bdh1p exhibits (2R,3R)-2,3-butanediol dehydrogenase activity, but Bdh1p also exhibit reductive activities towards lignocellulosic aldehyde inhibitors, such as acetaldehyde, glycolaldehyde, and furfural. No activity for glycolaldehyde or hexaldehyde with NADPH. Propionaldehyde is a poor substrate, no activity with glutaraldehyde
-
-
-
additional information
?
-
enzyme Bdh1p exhibits (2R,3R)-2,3-butanediol dehydrogenase activity, but Bdh2p also exhibit reductive activities towards lignocellulosic aldehyde inhibitors, such as acetaldehyde, glycolaldehyde, and furfural. No activity for furfural, propionaldehyde, or hexaldehyde with NADPH. Glutaraldehyde is a poor substrate
-
-
-
additional information
?
-
enzyme Bdh1p exhibits (2R,3R)-2,3-butanediol dehydrogenase activity, but Bdh2p also exhibit reductive activities towards lignocellulosic aldehyde inhibitors, such as acetaldehyde, glycolaldehyde, and furfural. No activity for furfural, propionaldehyde, or hexaldehyde with NADPH. Glutaraldehyde is a poor substrate
-
-
-
additional information
?
-
-
enzyme Bdh1p exhibits (2R,3R)-2,3-butanediol dehydrogenase activity, but Bdh2p also exhibit reductive activities towards lignocellulosic aldehyde inhibitors, such as acetaldehyde, glycolaldehyde, and furfural. No activity for furfural, propionaldehyde, or hexaldehyde with NADPH. Glutaraldehyde is a poor substrate
-
-
-
additional information
?
-
Saccharomyces cerevisiae YBA_08
enzyme Bdh1p exhibits (2R,3R)-2,3-butanediol dehydrogenase activity, but Bdh1p also exhibit reductive activities towards lignocellulosic aldehyde inhibitors, such as acetaldehyde, glycolaldehyde, and furfural. No activity for glycolaldehyde or hexaldehyde with NADPH. Propionaldehyde is a poor substrate, no activity with glutaraldehyde
-
-
-
additional information
?
-
Saccharomyces cerevisiae YBA_08
enzyme Bdh1p exhibits (2R,3R)-2,3-butanediol dehydrogenase activity, but Bdh1p also exhibit reductive activities towards lignocellulosic aldehyde inhibitors, such as acetaldehyde, glycolaldehyde, and furfural. No activity for glycolaldehyde or hexaldehyde with NADPH. Propionaldehyde is a poor substrate, no activity with glutaraldehyde
-
-
-
additional information
?
-
Saccharomyces cerevisiae YBA_08
enzyme Bdh1p exhibits (2R,3R)-2,3-butanediol dehydrogenase activity, but Bdh2p also exhibit reductive activities towards lignocellulosic aldehyde inhibitors, such as acetaldehyde, glycolaldehyde, and furfural. No activity for furfural, propionaldehyde, or hexaldehyde with NADPH. Glutaraldehyde is a poor substrate
-
-
-
additional information
?
-
Saccharomyces cerevisiae YBA_08
enzyme Bdh1p exhibits (2R,3R)-2,3-butanediol dehydrogenase activity, but Bdh2p also exhibit reductive activities towards lignocellulosic aldehyde inhibitors, such as acetaldehyde, glycolaldehyde, and furfural. No activity for furfural, propionaldehyde, or hexaldehyde with NADPH. Glutaraldehyde is a poor substrate
-
-
-
additional information
?
-
-
the purified enzyme glycerol dehydrogenase, GDH EC 1.1.1.6, also catalyzes the interconversion of (3S)-acetoin/meso-2,3-butanediol and (3R)-acetoin/(2R,3R)-2,3-butanediol. (2S,3S)-2,3-Butanediol is not a substrate for the GDH at all. Also no activity with 1-propanol, 1-butanol, isopentanol, ethylene glycol, ethanol, and (3S/3R)-acetoin in the oxidation reaction, and poor activity with formaldehyde in the reduction reaction
-
-
?
additional information
?
-
-
the purified enzyme glycerol dehydrogenase, GDH EC 1.1.1.6, also catalyzes the interconversion of (3S)-acetoin/meso-2,3-butanediol and (3R)-acetoin/(2R,3R)-2,3-butanediol. (2S,3S)-2,3-Butanediol is not a substrate for the GDH at all. Also no activity with 1-propanol, 1-butanol, isopentanol, ethylene glycol, ethanol, and (3S/3R)-acetoin in the oxidation reaction, and poor activity with formaldehyde in the reduction reaction
-
-
?
