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Information on EC 1.1.1.4 - (R,R)-butanediol dehydrogenase
for references in articles please use BRENDA:EC1.1.1.4
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EC Tree 1 Oxidoreductases
1.1 Acting on the CH-OH group of donors
1.1.1 With NAD+ or NADP+ as acceptor
1.1.1.4 (R,R)-butanediol dehydrogenase
IUBMB Comments
Also converts diacetyl into acetoin with NADH as reductant.
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
- 1.1.1.4
-
2r,3r-2,3-butanediol
- acetolactate
-
r-acetoin
- alpha-acetolactate
-
meso-2,3-bd
- polymyxa
- synthesis
showSynonyms
acetoin reductase, 2,3-butanediol dehydrogenase, butanediol dehydrogenase, (2r,3r)-2,3-butanediol dehydrogenase, meso-2,3-butanediol dehydrogenase, meso-bdh, bdh1p, ar/bdh, bdh2p, bdh99::67, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(2R,3R)-2,3-BDH
(2R,3R)-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
aminopropanol oxidoreductase
-
-
-
-
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
-
-
formerly
-
GDH
GldA
meso-2,3-butanediol dehydrogenase
MF996569
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
additional information
(2R,3R)-2,3-butanediol dehydrogenase
-
-
2,3-butanediol dehydrogenase
-
-
-
-
BDH1
-
essentially responsible for the formation of (2R,3R)-butane-2,3-diol and part of meso-butane-2,3-diol from (3R)-acetoin and (3S)-acetoin, respectively
R,R-2,3-butanediol dehydrogenase/meso-2,3-butanediol dehydrogenase/diacetyl reductase
-
R,R-2,3-butanediol dehydrogenase/meso-2,3-butanediol dehydrogenase/diacetyl reductase
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(R,R)-butane-2,3-diol + NAD+ = (R)-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
MetaCyc
(R,R)-butanediol biosynthesis, (R,R)-butanediol degradation
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SYSTEMATIC NAME
IUBMB Comments
(R,R)-butane-2,3-diol:NAD+ oxidoreductase
Also converts diacetyl into acetoin with NADH as reductant.
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CAS REGISTRY NUMBER
COMMENTARY
37250-09-2
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2R,3R)-2,3-butanediol + NAD+
(3R)-acetoin + NADH
-
Substrates: -
Products: -
Products: -
r
(2R,3R)-2,3-butanediol + NADP+
(R)-acetoin + NADPH + H+
Substrates: no detectable activity with (2S,3S)-2,3-butanediol
Products: -
Products: -
r
(2R,3R)-butane-2,3-diol + NAD+
?
Substrates: 69.5% activity compared to (2R,3R)-butane-2,3-diol
Products: -
Products: -
?
(3R)-acetoin + NADH + H+
(2R,3R)-butane-2,3-diol + NAD+
-
Substrates: -
Products: -
Products: -
?
(3S)-acetoin + NADH + H+
(2R,3S)-butane-2,3-diol + NAD+
-
Substrates: -
Products: -
Products: -
?
(R)-1,2-propanediol + NAD+
hydroxyacetone + NADH + H+
Substrates: 73% activity compared to (2R,3R)-butane-2,3-diol in the oxidation reaction, very low activity with the (S)-enantiomer
Products: -
Products: -
?
(R)-1-phenyl-1,2-ethanediol + NAD+
?
Substrates: 32.2% activity compared to (2R,3R)-butane-2,3-diol
Products: -
Products: -
?
(R)-acetoin + NADPH + H+
(2R,3R)-2,3-butanediol + NAD+
Substrates: -
Products: -
Products: -
?
(R)-acetoin + NADPH + H+
(2R,3R)-butane-2,3-diol + NADP+
Substrates: wild type enzyme does not use NADPH as coenzyme
Products: -
Products: -
?
(R,S)-3-hydroxy-2-pentanone + NADH
2,3-pentanediol + NAD+
-
Substrates: -
Products: -
Products: -
r
(R,S)-4-hydroxy-3-pentanone + NADH
2,3-pentanediol + NAD+
-
Substrates: -
Products: -
Products: -
r
1,2-hexanediol + NAD+
? + NADH + H+
Substrates: 50% activity compared to (2R,3R)-butane-2,3-diol in the oxidation reaction
Products: -
Products: -
?
1,2-pentandiol + NAD+
? + NADH + H+
Substrates: -
Products: -
Products: -
r
1,2-pentanediol + NAD+
? + NADH + H+
Substrates: 74% activity compared to (2R,3R)-butane-2,3-diol in the oxidation reaction
Products: -
Products: -
?
1,2-propandiol + NAD+
? + NADH + H+
Substrates: -
Products: -
Products: -
r
1,3-dihydroxyacetone + NADH + H+
?
-
Substrates: low activity
Products: -
Products: -
?
1-hydroxy-2-butanone + NADH + H+
?
-
Substrates: low activity
Products: -
Products: -
?
1-hydroxy-2-butanone + NADH + H+
? + NAD+
Substrates: -
Products: -
Products: -
?
1-hydroxy-2-propanone + NADH + H+
propane-1,2-diol + NAD+
-
Substrates: -
Products: -
Products: -
r
2,3-pentandione + NADH + H+
? + NAD+
Substrates: -
Products: -
Products: -
?
2-butanone + NADP+
2-butanol + NADPH + H+
Substrates: -
Products: -
Products: -
?
2-hydroxyacetophenone + NADH + H+
?
Substrates: 8.7% activity compared to (R)-acetoin
Products: -
Products: -
?
2-octanone + NADH + H+
?
Substrates: 9.3% activity compared to (R)-acetoin
Products: -
Products: -
?
2-pentanone + NADH + H+
(S)-2-pentanol + NAD+
-
Substrates: -
Products: -
Products: -
?
3,4-hexanedione + 2 NADH + 2 H+
(3R,4R)-3,4-hexanediol + 2 NAD+
Substrates: -
Products: -
Products: -
r
3-methyl-2-butenal + NADH + H+
?
Substrates: 16.7% activity compared to (R)-acetoin
Products: -
Products: -
?
acetoin + 2 NADPH + 2 H+
(2R,3R)-2,3-butanediol + meso-2,3-butanediol + 2 NADP+
Substrates: -
Products: -
Products: -
r
acetoin + NAD+
diacetyl + NADH
-
Substrates: 18% of the activity with 2,3-butanediol, in the reverse reaction 150% of the activity with acetoin
Products: -
Products: -
r
acetone + NADPH + H+
propan-2-ol + NADP+
Substrates: -
Products: -
Products: -
?
butane-1,2-diol + NAD+
? + NADH + H+
Substrates: -
Products: -
Products: -
?
butane-1,3-diol + NAD+
?
Substrates: 14.7% activity compared to (2R,3R)-butane-2,3-diol
Products: -
Products: -
?
butane-1,4-diol + NAD+
?
Substrates: 2.9% activity compared to (R,R)-butane-2,3-diol
Products: -
Products: -
?
butanone + NADPH + H+
butan-2-ol + NADP+
Substrates: -
Products: -
Products: -
?
cyclohexanone + NADH
?
-
Substrates: 38% of the activity with acetoin
Products: -
Products: -
?
diacetyl + 2 NADH + 2 H+
(2R,3R)-butane-2,3-diol + 2 NAD+
Substrates: -
Products: -
Products: -
r
diacetyl + NADH + H+
(3R)-acetoin + NAD+
Substrates: -
Products: -
Products: -
r
dihydroxyacetone + NADH
?
-
Substrates: 36% of the activity with acetoin
Products: -
Products: -
?
dihydroxyacetone phosphate + NADH
?
-
Substrates: 82% of the activity with acetoin
Products: -
Products: -
?
ethyl 4-chloro-3-hydroxybutyrate + NAD+
?
Substrates: 12.2% activity compared to (2R,3R)-butane-2,3-diol
Products: -
Products: -
?
formaldehyde + NADH + H+
? + NAD+
Substrates: -
Products: -
Products: -
?
formaldehyde + NADPH + H+
? + NADP+
Substrates: -
Products: -
Products: -
?
furfural + NADPH + H+
(furan-2-yl)methanol + NADP+
Substrates: -
Products: -
Products: -
?
glycolaldehyde + NADH + H+
? + NAD+
Substrates: -
Products: -
Products: -
?
hexaldehyde + NADH + H+
? + NAD+
Substrates: -
Products: -
Products: -
?
hexane-2,5-dione + NADH + H+
?
-
Substrates: low activity
Products: -
Products: -
?
isobutanol + NAD+
?
Substrates: 0.4% activity compared to (R,R)-butane-2,3-diol
Products: -
Products: -
?
meso-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
Substrates: -
Products: -
Products: -
?
n-butylaldehyde + NADH + H+
?
-
Substrates: low activity
Products: -
Products: -
?
pentane-1,2-diol + NAD+
?
-
Substrates: very low activity
Products: -
Products: -
?
pentane-2,3-dione + NADH + H+
?
-
Substrates: low activity
Products: -
Products: -
?
pentane-2,4-dione + NADH + H+
?
-
Substrates: low activity
Products: -
Products: -
?
propane-1,2-diol + NAD+
? + NADH + H+
Substrates: -
Products: -
Products: -
?
propane-1,3-diol + NAD+
?
Substrates: 1.4% activity compared to (R,R)-butane-2,3-diol
Products: -
Products: -
?
propionaldehyde + NADH + H+
? + NAD+
Substrates: -
Products: -
Products: -
?
pyruvic aldehyde + NADH
?
-
Substrates: 81% of the activity with acetoin
Products: -
Products: -
?
rac acetoin + NADH + H+
(2R,3R)-butane-2,3-diol + NAD+
Substrates: -
Products: -
Products: -
?
rac acetoin + NADH + H+
(2R,3S)-butane-2,3-diol + NAD+
Substrates: -
Products: -
Products: -
?
sodium lactate + NAD+
?
Substrates: 10.2% activity compared to (2R,3R)-butane-2,3-diol
Products: -
Products: -
?
(2R,3R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
Substrates: -
Products: -
Products: -
r
(2R,3R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
Alkalihalobacillus clausii DSM 8716T
Substrates: -
Products: -
Products: -
r
(2R,3R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
Substrates: -
Products: -
Products: -
r
(2R,3R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
Substrates: -
Products: -
Products: -
r
(2R,3R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
Substrates: -
Products: -
Products: -
?
(2R,3R)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
-
Substrates: -
Products: -
Products: -
?
(2R,3R)-butane-2,3-diol + NAD+
(3R,3S)-acetoin + NADH + H+
Substrates: preferred substrate
Products: -
Products: -
r
(2R,3R)-butane-2,3-diol + NAD+
(3R,3S)-acetoin + NADH + H+
Substrates: preferred substrate, very low activity with the (S)-enantiomer
Products: -
Products: -
r
(2R,3R)-butane-2,3-diol + NAD+
(3R,3S)-acetoin + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(2R,3R)-butane-2,3-diol + NAD+
(3R,3S)-acetoin + NADH + H+
Substrates: 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
Products: -
Products: -
r
(2R,3R)-butane-2,3-diol + NAD+
(3R,3S)-acetoin + NADH + H+
Substrates: sole product in the reduction reaction, preferred substrate in the oxidation reaction
Products: preferred substrate in the reduction reaction
Products: preferred substrate in the reduction reaction
r
(2R,3R)-butane-2,3-diol + NAD+
(3R,3S)-acetoin + NADH + H+
Substrates: 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
Products: -
Products: -
r
(2R,3R)-butane-2,3-diol + NAD+
(3R,3S)-acetoin + NADH + H+
Substrates: sole product in the reduction reaction, preferred substrate in the oxidation reaction
Products: preferred substrate in the reduction reaction
Products: preferred substrate in the reduction reaction
r
(2R,3R)-butane-2,3-diol + NAD+
(3R,3S)-acetoin + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(2R,3R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(2R,3R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(2R,3R)-butane-2,3-diol + NAD+
(R)-acetoin + NADH + H+
Substrates: -
Products: -
Products: -
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
Substrates: -
Products: -
Products: -
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
Substrates: slightly preferred substrate
Products: -
Products: -
r
(2R,3S)-butane-2,3-diol + NAD+
(3R)-acetoin + NADH + H+
Substrates: -
Products: -
Products: -
r
(2R,3S)-butane-2,3-diol + NAD+