Ligand acetoin

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Basic Ligand Information

Molecular Structure
Picture of acetoin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C4H8O2
acetoin
ROWKJAVDOGWPAT-UHFFFAOYSA-N
Synonyms:
(3R,3S)-acetoin, (R,S)-acetoin, (R/S)-acetoin, 2-hydroxy-3-butanone, 3-hydroxy-2-butanone, 3-hydroxy-butane-2-one, 3-hydroxybutan-2-one, 3-hydroxybutane-2-one, 3-hydroxybutanone, 3-methylbutanone, butan-2-ol-3-one, DL-acetoin, L-acetoin

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-hydroxybutan-2-one + D-ribose 5-phosphate = acetaldehyde + 1-deoxy-D-altro-heptulose 7-phosphate
show the reaction diagram
-
DL-Acetoin = ?
show the reaction diagram
-

In Vivo Product 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
-
-
diacetyl + NAD(P)H = acetoin + NADP+
show the reaction diagram
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(2R,3R)-butane-2,3-diol + NAD+ = (3R,3S)-acetoin + NADH + H+
show the reaction diagram
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-
(2R,3S)-butane-2,3-diol + NAD+ = acetoin + NADH + H+
show the reaction diagram
-
-
pyruvate + acetaldehyde = acetoin + CO2
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (42 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetoin + NAD+ = butan-2,3-dione + NADH + H+
show the reaction diagram
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acetoin + NADPH + H+ = ?
show the reaction diagram
-
acetoin + NADPH = ?
show the reaction diagram
-
acetoin + NADPH + H+ = 2,3-butanediol + NADP+
show the reaction diagram
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2-hydroxy-3-butanone + NADPH = 2,3-dihydroxybutanol + NADP+
show the reaction diagram
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3-hydroxy-2-butanone + NAD+ = 2,3-butandione + NADH
show the reaction diagram
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acetoin + NADH = ? + NAD+
show the reaction diagram
-
acetoin + NADH + H+ = 2,3-butanediol + NAD+
show the reaction diagram
-
acetoin + NAD(P)H + H+ = 2,3-butanediol + NAD(P)+
show the reaction diagram
-
(R/S)-acetoin + NADPH = (2S,3S)-2,3-butanediol + NADP+
show the reaction diagram
-
acetoin + NADP+ = ?
show the reaction diagram
-
3-hydroxybutan-2-one + D-ribose 5-phosphate = acetaldehyde + 1-deoxy-D-altro-heptulose 7-phosphate
show the reaction diagram
-
acetoin + 2,6-dichlorophenolindophenol = acetaldehyde + ?
show the reaction diagram
-
DL-Acetoin = ?
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (42 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
diacetyl + NADPH = acetoin + NADP+
show the reaction diagram
-
-
2,3-butanediol + NADP+ = 3-hydroxybutan-2-one + NADPH
show the reaction diagram
-
diacetyl + NAD(P)H = acetoin + NADP+
show the reaction diagram
-
diacetyl + NADH = L-acetoin + NAD+
show the reaction diagram
-
diacetyl + NADPH + H+ = acetoin + NADP+
show the reaction diagram
-
-
butane-2,3-dione + NADPH = acetoin + NADP+
show the reaction diagram
-
-
2,3-butanediol + NAD+ = 3-hydroxybutane-2-one + NADH
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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2,3-butanediol + ferricyanide = 3-hydroxybutan-2-one + ferrocyanide
show the reaction diagram
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2 butane-2,3-dione = acetylacetoin + acetoin
show the reaction diagram
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alpha-acetolactate + CO2 = acetoin
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
probably all L(+)-alpha-hydroxycarbonyls products inhibit uncompetitively at non-saturated concentrations
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noncompetitive, product inhibition
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competitive inhibition, Ki: 4.1 mM
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (16 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.097
-
at pH 7.4 and 37°C
183
-
pH 7.5, 37°C
142
-
cosubstrate: NADPH, pH 7.5, 80°C
13.7
-
with NADH as cosubstrate, at pH 6.0 and 70°C
6
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pH 7.0, 30°C

KM Value (37 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
29
-
-
13
-
-
16
-
pH 7.5, 37°C
0.32
-
cosubstrate: NADPH, pH 7.5, 80°C
62
-
-
30.2
-
with NADH as cosubstrate, at pH 6.0 and 70°C
0.23
-
racemic (R/S)-acetoin, pH 7.0, 30°C, recombinant enzyme
0.0028
-
E1 complex, 80°C, pH 7.0; E1 complex, 80°C, pH 7.0

References & Links

Links to other databases for acetoin

ChEBI
PubChem
ChEBI
PubChem