Ligand butane-2,3-dione

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Basic Ligand Information

Molecular Structure
Picture of butane-2,3-dione (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C4H6O2
butane-2,3-dione
QSJXEFYPDANLFS-UHFFFAOYSA-N
Synonyms:
2,3 butanedione, 2,3-butadione, 2,3-butandione, 2,3-Butanedione, 2,3-butendione, Butan-2,3-dione, butane 2,3-dione, Butanedione, diacetyl, dimethylglyoxal


Show all pahtways known for Show all BRENDA pathways known for butane-2,3-dione

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
diacetyl + NAD(P)H = acetoin + NAD(P)+
show the reaction diagram
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diacetyl + NAD(P)H = acetoin + NADP+
show the reaction diagram
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diacetyl + NADH + H+ = (R)-acetoin + NAD+
show the reaction diagram
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diacetyl + NADH + H+ = (S)-acetoin + NAD+
show the reaction diagram
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diacetyl + NADH + H+ = (3S)-acetoin + NAD+
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetoin + NAD(P)H + H+ = butan-2,3-dione + NAD(P)H + H+
show the reaction diagram
-
-
olmesartan medoxomil + H2O = olmesartan + diacetyl
show the reaction diagram
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-

Substrate in Enzyme-catalyzed Reactions (63 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2,3-butanedione + NAD(P)H = 2,3-butanediol + NAD(P)+
show the reaction diagram
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diacetyl + NADPH = ? + NADP+
show the reaction diagram
-
diacetyl + NAD(P)H = acetoin + NADP+
show the reaction diagram
-
diacetyl + NADH = L-acetoin + NAD+
show the reaction diagram
-
2,3-butanedione + NADPH + H+ = ?
show the reaction diagram
-
diacetyl + NADH = ?
show the reaction diagram
-
2,3-butanedione + NADH + H+ = ? + NAD+
show the reaction diagram
-
diacetyl + NAD(P)H = ? + NAD(P)+
show the reaction diagram
-
diacetyl + NADPH = ? + NADP+
show the reaction diagram
-
butane-2,3-dione + NADPH = acetoin + NADP+
show the reaction diagram
-
diacetyl + NADH + H+ = (R)-acetoin + NAD+
show the reaction diagram
-
diacetyl + NADPH + H+ = ? + NADP+
show the reaction diagram
-
diacetyl + NADPH + H+ = ?
show the reaction diagram
-
diacetyl + NADH = ?
show the reaction diagram
-
dimethylglyoxal + NADPH + H+ = ? + NADP+
show the reaction diagram
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2,3-butandione + NAD(P)H = butan-2-ol-3-one + NAD(P)+
show the reaction diagram
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diacetyl + NADH + H+ = (3S)-acetoin + NAD+
show the reaction diagram
-
2,3-butanedione + NADPH + H+ = (R)-2-hydroxy-3-oxo-butane + NADP+
show the reaction diagram
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diacetyl + NADPH = ?
show the reaction diagram
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diacetyl + 2,6-dichlorophenolindophenol = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetoin + NAD+ = diacetyl + NADH
show the reaction diagram
-
-
acetoin + NAD+ = butan-2,3-dione + NADH + H+
show the reaction diagram
-
-
3-hydroxy-2-butanone + NAD+ = 2,3-butandione + NADH
show the reaction diagram
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acetoin + NAD+ = diacetyl + NADH
show the reaction diagram
-
-
acetoin + NAD(P)H + H+ = butan-2,3-dione + NAD(P)H + H+
show the reaction diagram
-
-
olmesartan medoxomil + H2O = olmesartan + diacetyl
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
115% activity at 10 mM
-
activates
-
140% activity at 0.2 mM
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Inhibitor in Enzyme-catalyzed Reactions (88 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
irreversible inactivation
substrate inhibition at concentrations above 80-90 mM
-
pseudo-first-order loss of oxidative decarboxylase activity
-
inactivation, enzyme regains activity after removal of ketone
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40 mM, pH 8.5, t1/2: 2 h
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90% inactivation at 50 mM after 90 min in 50 mM borate buffer, gel filtration in 50 mM phosphate buffer causes a recovery of 92% activiy
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reversible
-
modification of 12 Arg residues per molecule results in complete inactivation. NAD+ protects
-
inhibitor of transhydrogenase and diaphorase activity, reacts with arginine residue involved in binding of pyridine nucleotides
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10 mM, biphasic kinetic, complete inactivation after 20 min
-
slight inactivation
-
good substrates but not poor substrates protect against inactivation
-
10 mM, complete inhibition after 50 min in borate buffer, inhibition is fully reversible upon removal of borate
-
protection by L-leucine, NADH and 2-oxoglutarate
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1 mM, 55% inhibition
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5 mM, 54% and 21% inhibition of microsomal and mitochondrial acyltransferase respectively
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inactivation
-
at 10 mM, in presence of borate buffer pH 9.0
-
almost complete loss of wild-type enzyme activity after 10 min at 10 mM
-
slight inhibition at high concentrations
-
irreversible. UDP-glucuronic acid protects, no protection by UDP-glucose. Activity of H308R towards UDP-glucose is unaffected by the reagent
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46% residual activity at 10 mM
-
results in a rapid loss of the component B activity. Component A is resistant, retaining the initial activity almost completely. Farnesyl diphosphate, isopentenyl diphosphate, farnesyl monophosphate and inorganic diphosphate protect the synthase against the inactivation by N-ethylmaleimide, farnesyl diphosphate being the most effective. The presence of Mg2+ is essential for the protection by isopentenyl diphosphate and inorganic diphosphate. For protection of the synthase activity against the inactivation by 2,3-butanedione, the presence of farnesyl diphosphate, isopentenyl diphosphate and Mg2+ is more effective than that of the individual substrates and Mg2+. Inorganic diphosphate provides substantial protection. In the absence of component A, the component B activity is not protected by any substrates or its analogue
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in borate buffer, inactivation, implying the presence of an essential arginine
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significant inhibition in the presence of borate, protection by adenosine 5'-phosphosulfate, ATP or MgATP2- plus nitrate
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slow but complete inactivation
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Arg-specific modification reagent; SULT1A1, inactivation
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10 mM, 90% inhibition
-
preincubation with bestatin partially protects enzyme from inactivation
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photochemical inactivation: effect only in the light, proportional to light intensity, modification of 5 Trp-, 3-4 Tyr-, 2 His- and 2Arg-residues, no photoinactivation in the absence of oxygen or in the presence of azide, protection also by Trp, Met, D-Met, L-2-thiol-His, 2-mercaptoethanol, Gly-Met, Ki: 5.1-19.8 mM
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10 mM, 97.4% inhibition
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50 mM, 78% loss of activity, benzylpenicillin or phenylacetate protects
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modification of Arg causes about 50% inhibition of forward and reverse reaction
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inactivation half-life: 21.8 min at 0.1 mM
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phosphoenolpyruvate, ADP and Mn2+, alone or in combination protect against inactivation
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0.1 mM, complete inhibition
-
protection by 5-aminolevulinate
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inactivation, arginine-specific reagent
-
reacts with Arg residues, causes a slight decrease in activity
-
time and concentration dependent inactivation
-
protection by substrates and competitive inhibitors
-
inactivation
-
inactivation by modification of arginine residues, ATP protects
-
magnesiumdiphosphate and analogues protect
-
40 mM, almost complete inactivation of enzyme activity in chromatophores after 12 min, NAD+ and NADP+ partially protect, complete protection by a combination of NAD+ and NADP+
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3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (24 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
28.3
-
pH 7.4, 25°C
0.158
-
at pH 7.4 and 37°C
609
-
pH 7.5, 37°C
202
-
cosubstrate: NADPH, pH 7.5, 80°C
0.333
-
in 0.1 M potassium phosphate, pH 7.4
0.167
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
6.11
-
at pH 10.0 and 45°C
0.167
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
1222
-
at pH 5.0 and 30°C
11.5
-
pH 8.0, 40°C
36.1
-
pH 7.4, 30°C

KM Value (67 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
54
-
pH 7.4, 25°C
0.39
-
-
0.68
-
in 0.1 M potassium phosphate, pH 7.4
0.42
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
4
-
pH 8.8, 45°C
0.9
-
at pH 7.0 and 30°C
0.42
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
72.4
-
at pH 5.0 and 30°C
3.3
-
pH 8.0, 40°C
0.72
-
pH 7.4, 30°C
0.8
-
2,3-butanedione

Ki Value (4 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
300
-
25°C, pH 6.0
23
-
-
5.1
19.8
photochemical inactivation: effect only in the light, proportional to light intensity, modification of 5 Trp-, 3-4 Tyr-, 2 His- and 2Arg-residues, no photoinactivation in the absence of oxygen or in the presence of azide, protection also by Trp, Met, D-Met, L-2-thiol-His, 2-mercaptoethanol, Gly-Met
4.1
-
-

References & Links

Links to other databases for butane-2,3-dione

ChEBI
PubChem
ChEBI
PubChem