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Enzyme Nomenclature
Information on EC 1.1.1.304 - diacetyl reductase [(S)-acetoin forming]
Word Map on EC 1.1.1.304
- 1.1.1.304
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subsp
-
reductases
- lactis
-
lactococcus
-
alpha-dicarbonyls
- l-xylulose
- pigeon
- alpha-acetolactate
-
lipoic
- casei
- xylitol
- synthesis
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
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EC NUMBER 
COMMENTARY 
1.1.1.304
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RECOMMENDED NAME
GeneOntology No.
diacetyl reductase [(S)-acetoin forming]
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(S)-acetoin + NAD+ = diacetyl + NADH + H+
Theorell-Chance mechanism with NADH as the leading substrate
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(S)-acetoin + NAD+ = diacetyl + NADH + H+
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
(S)-acetoin:NAD+ oxidoreductase
The reaction is catalysed in the reverse direction. This activity is usually associated with butanediol dehydrogenase activity (EC 1.1.1.4 or EC 1.1.1.76). While the butanediol dehydrogenase activity is reversible, diacetyl reductase activity is irreversible. This enzyme has been reported in the bacteria Geobacillus stearothermophilus, Enterobacter aerogenes and Klebsiella pneumoniae [1-3]. Different from EC 1.1.1.303, diacetyl reductase [(R)-acetoin forming].
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
bifunctional diacetyl reductase and (R)-2,3-butanediol dehydrogenase
UniProt
bifunctional diacetyl reductase and (R)-2,3-butanediol dehydrogenase
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
metabolism
evolution
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the enzyme belongs to the family of the short-chain dehydrogenase/reductases
evolution
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the enzyme belongs to the family of the short-chain dehydrogenase/reductases
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metabolism
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acetoin(diacetyl) reductase, also known as 2,3-butanediol dehydrogenase, is one of the key enzymes in the microbial production of 2,3-butanediol
metabolism
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the enzyme is involved in the butanediol cycle, overview
metabolism
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the enzyme is involved in the butanediol cycle, overview
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metabolism
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acetoin(diacetyl) reductase, also known as 2,3-butanediol dehydrogenase, is one of the key enzymes in the microbial production of 2,3-butanediol
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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
2,3-pentanedione + beta-NADH + H+
L-3-hydroxy-2-pentanone + beta-NAD+
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ir
diacetyl + beta-NADH + H+
(S)-acetoin + beta-NAD+
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86.9% of the activity with pentane-2,3-dione
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ir
ethyl pyruvate + beta-NADH + H+
? + beta-NAD+
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38.4% of the activity with pentane-2,3-dione
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ir
ethyl pyruvate + NADH + H+
? + NAD+
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57.7% of the activity with diacetyl
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?
methyl glyoxal + NADH + H+
? + NAD+
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11% of the activity with diacetyl
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?
methyl pyruvate + beta-NADH + H+
? + beta-NAD+
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22.8% of the activity with pentane-2,3-dione
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ir
methyl pyruvate + NADH + H+
? + NAD+
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49% of the activity with diacetyl
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?
2,3-pentanedione + NADH + H+
3-hydroxy-2-pentanone + NAD+
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85.6% of the activity with diacetyl
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?
2,3-pentanedione + NADH + H+
3-hydroxy-2-pentanone + NAD+
77% of the (R)-2,3-butanediol dehydrogenase activity with substrate acetoin
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?
diacetyl + NADH + H+
(S)-acetoin + NAD+
87% of the (R)-2,3-butanediol dehydrogenase activity with substrate acetoin
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?
additional information
?
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the enzyme shows an S-enantioselectivity in the reversible reduction of acetoin so it might be responsible of the meso-butenediol formation from R-acetoin. It acts on racemic acetoin and (S)-acetoin to form (2S,3S)-butane-2,3-diol, EC 1.1.1.76, but also on the (2R,3R)-butane-2,3-diol isomer in the reverse reaction, EC 1.1.1.4
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additional information
?
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the enzyme shows an S-enantioselectivity in the reversible reduction of acetoin so it might be responsible of the meso-butenediol formation from R-acetoin. It acts on racemic acetoin and (S)-acetoin to form (2S,3S)-butane-2,3-diol, EC 1.1.1.76, but also on the (2R,3R)-butane-2,3-diol isomer in the reverse reaction, EC 1.1.1.4
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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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KC505218
the enzyme also catalyzes the stereospcific reaction of (S)-acetoin reduction to butanediol, EC 1.1.1.76
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additional information
?
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the enzyme also catalyzes the stereospcific reaction of (S)-acetoin reduction to butanediol, EC 1.1.1.76
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additional information
?
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KC505218
the enzyme also catalyzes the stereospcific reaction of (S)-acetoin reduction to butanediol, EC 1.1.1.76
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additional information
?
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the enzyme also catalyzes the stereospcific reaction of (S)-acetoin reduction to butanediol, EC 1.1.1.76
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additional information
?
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Rhodococcus erythropolis WZ010 is capable of producing optically pure (2S,3S)-2,3-butanediol in alcoholic fermentation.
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additional information
?
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the enzyme displays absolute stereospecificity in the reduction of diacetyl to (2S,3S)-2,3-butanediol via (S)-acetoin. The enzyme shows higher catalytic efficiency for (S)-1-phenylethanol oxidation than that for acetophenone reduction. ReADR-catalyzed asymmetric reduction of diacetyl is coupled with stereoselective oxidation of 1-phenylethanol, which simultaneously forms both (2S,3S)-2,3-butanediol and (R)-1-phenylethanol in great conversions and enantiomeric excess values.The enzyme accepts a broad range of substrates including aliphatic and aryl alcohols, aldehydes, and ketones
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additional information
?
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Rhodococcus erythropolis WZ010 is capable of producing optically pure (2S,3S)-2,3-butanediol in alcoholic fermentation.
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-
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additional information
?
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the enzyme displays absolute stereospecificity in the reduction of diacetyl to (2S,3S)-2,3-butanediol via (S)-acetoin. The enzyme shows higher catalytic efficiency for (S)-1-phenylethanol oxidation than that for acetophenone reduction. ReADR-catalyzed asymmetric reduction of diacetyl is coupled with stereoselective oxidation of 1-phenylethanol, which simultaneously forms both (2S,3S)-2,3-butanediol and (R)-1-phenylethanol in great conversions and enantiomeric excess values.The enzyme accepts a broad range of substrates including aliphatic and aryl alcohols, aldehydes, and ketones
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additional information
?
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no activity with alpha-NADH or NADPH
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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
additional information
?
-
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the enzyme shows an S-enantioselectivity in the reversible reduction of acetoin so it might be responsible of the meso-butenediol formation from R-acetoin. It acts on racemic acetoin and (S)-acetoin to form (2S,3S)-butane-2,3-diol, EC 1.1.1.76, but also on the (2R,3R)-butane-2,3-diol isomer in the reverse reaction, EC 1.1.1.4
-
-
-
additional information
?
-
-
the enzyme shows an S-enantioselectivity in the reversible reduction of acetoin so it might be responsible of the meso-butenediol formation from R-acetoin. It acts on racemic acetoin and (S)-acetoin to form (2S,3S)-butane-2,3-diol, EC 1.1.1.76, but also on the (2R,3R)-butane-2,3-diol isomer in the reverse reaction, EC 1.1.1.4
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additional information
?
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KC505218
the enzyme also catalyzes the stereospcific reaction of (S)-acetoin reduction to butanediol, EC 1.1.1.76
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-
-
additional information
?
-
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the enzyme also catalyzes the stereospcific reaction of (S)-acetoin reduction to butanediol, EC 1.1.1.76
-
-
-
additional information
?
-
KC505218
the enzyme also catalyzes the stereospcific reaction of (S)-acetoin reduction to butanediol, EC 1.1.1.76
-
-
-
additional information
?
-
-
the enzyme also catalyzes the stereospcific reaction of (S)-acetoin reduction to butanediol, EC 1.1.1.76
-
-
-
additional information
?
-
-
Rhodococcus erythropolis WZ010 is capable of producing optically pure (2S,3S)-2,3-butanediol in alcoholic fermentation.
-
-
-
additional information
?
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Rhodococcus erythropolis WZ010 is capable of producing optically pure (2S,3S)-2,3-butanediol in alcoholic fermentation.
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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addition of EDTA or the cations at 1 mM, such as Na+, K+, Mn2+, Mg2+, and Ca2+, have no significant effect on the activity of ReADR
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Methyl pyruvate
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substrate inhibition at concentrations above 80-90 mM
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
DMSO
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DMSO at a final concentration of 30% v/v added into the assay mixture, increases the activity up to 120% of the control enzyme activity
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
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Michaelis-Menten-type kinetics
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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PDB
SCOP
CATH
ORGANISM
UNIPROT
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
homodimer
tetramer
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
unstable to dilution, kept diluted at 0°C for ca. 60 min it will lose 62% of activity. This inactivation is almost completely reversed by the addition of NAD+
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ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
DMSO
DMSO
-
the enzyme retains 53.6% of the initial activity after 4 h incubation with 30% v/v DMSO at 4°C
DMSO
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the enzyme retains 53.6% of the initial activity after 4 h incubation with 30% v/v DMSO at 4°C
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
storage at 0°C in the presence of 20% glycerol, 0.1 mM EDTA, 5 mM 2-mercaptoethanol and 0.6 mM NAD+ in TEA buffer, pH 7.5, half-life of one month
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme by adsorption on diethylaminoethyl–Sepharose and hydrophobic interaction chromatography
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recombinant enzyme from Escherichia coli strain Rosetta (DE3)
KC505218
recombinant His-tagged enzyme from Escherichia coli by nickel affinity chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene adr, DNA and amino acid sequence determination and analysis, sequence comparison, expression of His-tagged enzyme in Escherichia coli
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gene dar, fucntional expression in Escherichia coli strain Rosetta (DE3), resulting in production of S-acetoin with higher than 99.9% optical purity from diacetyl
KC505218
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
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acetoin(diacetyl) reductase, i.e. 2,3-butanediol dehydrogenase, is one of the key enzymes in the microbial production of 2,3-butanediol, a platform with extensive industrial applications in the production of plastics, printing inks, perfumes, fumigants, spandex, moistening and softening agents, plasticizers, and pharmaceutical carrier
synthesis
KC505218
the enzyme is used for production of S-acetoin with higher than 99.9% optical purity from diacetyl using whole cells of engineered Escherichia coli
synthesis
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the enzyme is used for production of S-acetoin with higher than 99.9% optical purity from diacetyl using whole cells of engineered Escherichia coli
-
synthesis
-
acetoin(diacetyl) reductase, i.e. 2,3-butanediol dehydrogenase, is one of the key enzymes in the microbial production of 2,3-butanediol, a platform with extensive industrial applications in the production of plastics, printing inks, perfumes, fumigants, spandex, moistening and softening agents, plasticizers, and pharmaceutical carrier
-
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LINKS TO OTHER DATABASES (specific for EC-Number 1.1.1.304)
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