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Ligand acetoin

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

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

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Show Natural Substrate (6 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.71

acetoin + NAD(P)+ = butan-2,3-dione + NAD(P)H + H+

735486

-

1.1.1.71

acetoin + NAD(P)H + H+ = 2,3-butanediol + NAD(P)+

735486

-

1.1.1.B20

acetoin + NADH + H+ = (2R,3S)-butane-2,3-diol + NAD+

742158, 742152

-

1.1.1.B20

acetoin + NADH + H+ = meso-2,3-butanediol + NAD+

742149

-

1.1.1.71

2 entries

1.1.1.B20

2 entries

2.2.1.4

3-hydroxybutan-2-one + D-ribose 5-phosphate = acetaldehyde + 1-deoxy-D-altro-heptulose 7-phosphate

486058

-

5.1.2.4

DL-Acetoin = ?

389576, 389577

-

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

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Show Natural Product (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.10

diacetyl + NAD(P)H = acetoin + NAD(P)+

0

-

1.1.1.162

diacetyl + NAD(P)H = acetoin + NADP+

286091

-

1.1.1.4

(2R,3R)-butane-2,3-diol + NAD+ = (3R,3S)-acetoin + NADH + H+

0

-

1.1.1.B20

(2R,3S)-butane-2,3-diol + NAD+ = acetoin + NADH + H+

0

-

4.1.1.1

pyruvate + acetaldehyde = acetoin + CO2

0

-

Substrate in Enzyme-catalyzed Reactions (47 results)

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Show Substrate (47 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

3-hydroxy-2-butanone + NADH + H+ = 2,3-butanediol + NAD+

744545

-

1.1.1.1

3-hydroxy-2-butanone + NADPH + H+ = 2,3-butanediol + NADP+

744545

-

1.1.1.1

acetoin + NAD+ = diacetyl + NADH

667266

-

1.1.1.1

acetoin + NADH + H+ = 2,3-butanediol + NAD+

735486

-

1.1.1.1

acetoin + NADH + H+ = 3-hydroxy-2-butanol + NAD+

721868

-

1.1.1.1

acetoin + NADH + H+ = butan-2,3-diol + NAD+

667266

-

1.1.1.1

6 entries

1.1.1.103

acetoin + NAD+ = butan-2,3-dione + NADH + H+

729112

-

1.1.1.149

acetoin + NADPH + H+ = ?

740126, 285999

-

1.1.1.153

acetoin + NADPH = ?

286021, 286020

-

1.1.1.162

acetoin + NADPH + H+ = 2,3-butanediol + NADP+

286091

-

1.1.1.184

2-hydroxy-3-butanone + NADPH = 2,3-dihydroxybutanol + NADP+

686056

-

1.1.1.2

acetoin + NADPH + H+ = 2,3-butanediol + NADP+

738511

-

1.1.1.2

acetoin + NADPH + H+ = butan-2,3-diol + NADP+

286184

-

1.1.1.2

2 entries

1.1.1.254

3-hydroxy-2-butanone + NAD+ = 2,3-butandione + NADH

285735

-

1.1.1.4

(3R,3S)-acetoin + NADH = (2R,3R)-2,3-butanediol + meso-2,3-butanediol + NAD+

246409, 246413, 740827

-

1.1.1.4

acetoin + 2 NADPH + 2 H+ = (2R,3R)-2,3-butanediol + meso-2,3-butanediol + 2 NADP+

737501

-

1.1.1.4

acetoin + NAD+ = diacetyl + NADH

667266

-

1.1.1.4

acetoin + NADH + H+ = (R,R)-butanediol + NAD+

740952

-

1.1.1.4

acetoin + NADH + H+ = 2,3-butanediol + NAD+

246407, 246410, 246412, 246411

-

1.1.1.4

acetoin + NADH = 2,3-butanediol + NAD+

695754

-

1.1.1.4

acetoin + NADPH + H+ = (R,R)-butanediol + NADP+

740952

-

1.1.1.4

7 entries

1.1.1.406

acetoin + NADH = ? + NAD+

389404

-

1.1.1.427

(R/S)-acetoin + NADPH = (2S,3S)-2,3-butanediol + NADP+

710944

-

1.1.1.427

acetoin + NADP+ = diacetyl + NADPH + H+

764192

-

1.1.1.427

2 entries

1.1.1.6

acetoin + NADH + H+ = 2,3-butanediol + NAD+

654039

-

1.1.1.71

acetoin + NAD(P)+ = butan-2,3-dione + NAD(P)H + H+

735486

-

1.1.1.71

acetoin + NAD(P)H + H+ = 2,3-butanediol + NAD(P)+

735486

-

1.1.1.71

acetoin + NADPH + H+ = ?

740851

-

1.1.1.76

(R,S)-acetoin + NADH + H+ = (2S,3S)-2,3-butanediol + meso-2,3-butanediol + NAD+

737865

-

1.1.1.76

(R,S)-acetoin + NADPH = (2S,3S)-2,3-butanediol + meso-2,3-butanediol + NADP+

710944

-

1.1.1.76

L-acetoin + NADH + H+ = (S,S)-butane-2,3-diol + NAD+

389580

-

1.1.1.76

L-acetoin + NADH + H+ = (S,S)-butanediol + NAD+

389578

-

1.1.1.76

L-acetoin + NADH = L-2,3-butanediol

389573, 389575, 389576, 389577, 389578, 389580, 389574

-

1.1.1.71

3 entries

1.1.1.76

5 entries

1.1.1.81

acetoin + NAD(P)H + H+ = 2,3-butanediol + NAD(P)+

287375

-

1.1.1.B20

2 (R,S)-acetoin + 2 NADPH + 2 H+ = (2S,3S)-2,3-butanediol + meso-2,3-butanediol + NADP+

710944

-

1.1.1.B20

2 acetoin + 2 NADH + 2 H+ = (2S,3S)-2,3-butanediol + meso-2,3-butanediol + 2 NAD+

741710

-

1.1.1.B20

acetoin + NADH + H+ = (2R,3S)-butane-2,3-diol + NAD+

742158, 742152

-

1.1.1.B20

acetoin + NADH + H+ = meso-2,3-butanediol + NAD+

742149

-

1.1.1.B20

L-acetoin + NADH = L-2,3-butanediol + NAD+

246408

-

1.1.1.B20

5 entries

1.3.1.20

acetoin + NADP+ = ?

349254

-

1.4.1.28

3-hydroxy-2-butanone + NH3 + NADH + H+ = 3-amino-butan-2-ol + NAD+ + H2O

763366

-

1.4.1.28

3-hydroxy-2-butanone + NH3 + NADH + H+ = 3-aminobutan-2-ol + H2O + NAD+

763366

-

1.4.1.28

3-hydroxybutan-2-one + NH3 + NADH + H+ = 3-aminobutan-2-ol + NAD+ + H2O

763489

-

1.4.1.28

3 entries

2.2.1.4

3-hydroxybutan-2-one + D-ribose 5-phosphate = acetaldehyde + 1-deoxy-D-altro-heptulose 7-phosphate

486058

-

2.3.1.190

acetoin + 2,6-dichlorophenolindophenol = acetaldehyde + ?

486168, 703733, 704245

-

2.3.1.190

acetoin + CoA + NAD+ = acetaldehyde + acetyl-CoA + NADH + H+

756608

-

2.3.1.190

2 entries

5.1.2.4

DL-Acetoin = ?

389576, 389577

-

Product in Enzyme-catalyzed Reactions (43 results)

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Show Product (43 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

2,3-butanediol + NAD+ = 3-hydroxy-2-butanone + NADH + H+

0

-

1.1.1.1

2,3-butanediol + NADP+ = 3-hydroxy-2-butanone + NADPH + H+

0

-

1.1.1.1

3-methylbutanol + NAD+ = 3-methylbutanone + NADH + H+

0

-

1.1.1.1

2,3-butanediol + NAD+ = acetoin + NADH + H+

0

-

1.1.1.1

2,3-butanediol + NADP+ = acetoin + NADPH + H+

0

-

1.1.1.1

butan-2,3-diol + NAD+ = acetoin + NADH + H+

0

-

1.1.1.1

diacetyl + NADH + H+ = acetoin + NAD+

0

-

1.1.1.10

diacetyl + NAD(P)H = acetoin + NAD(P)+

0

-

1.1.1.10

diacetyl + NADPH + H+ = acetoin + NADP+

0

-

1.1.1.1

7 entries

1.1.1.10

2 entries

1.1.1.153

diacetyl + NADPH = acetoin + NADP+

0

-

1.1.1.156

2,3-butanediol + NADP+ = 3-hydroxybutan-2-one + NADPH

286042, 286040

-

1.1.1.162

diacetyl + NAD(P)H = acetoin + NADP+

286091

-

1.1.1.184

2,3-butanediol + NADP+ = acetoin + NADPH + H+

0

-

1.1.1.184

diacetyl + NADPH + H+ = acetoin + NADP+

0

-

1.1.1.184

2 entries

1.1.1.185

diacetyl + NADH = L-acetoin + NAD+

0, 286137

-

1.1.1.2

2,3-butanediol + NADP+ = acetoin + NADPH + H+

0

-

1.1.1.2

diacetyl + NADPH + H+ = acetoin + NADP+

0

-

1.1.1.2

2 entries

1.1.1.292

butane-2,3-dione + NADPH = acetoin + NADP+

0

-

1.1.1.4

(2R,3R)-butane-2,3-diol + NAD+ = (3R,3S)-acetoin + NADH + H+

0

-

1.1.1.4

(3R,3S)-butane-2,3-diol + NAD+ = (3R,3S)-acetoin + NADH + H+

0

-

1.1.1.4

2,3-butanediol + NAD+ = acetoin + NADH

246412, 246411, 246407, 0, 246410

-

1.1.1.4

2,3-butanediol + NAD+ = acetoin + NADH + H+

0

-

1.1.1.4

diacetyl + NADH + H+ = acetoin + NAD+

0

-

1.1.1.4

meso-butane-2,3-diol + NAD+ = acetoin + NADH + H+

0

-

1.1.1.4

6 entries

1.1.1.427

diacetyl + NADPH + H+ = acetoin + NADP+

0

-

1.1.1.6

2,3-butanediol + NAD+ = 3-hydroxybutane-2-one + NADH

636283, 0, 636286

-

1.1.1.6

racemic 2,3-butanediol + NAD+ = 3-hydroxybutane-2-one + NADH + H+

0

-

1.1.1.76

(2S,3S)-2,3-butanediol + NAD+ = (R,S)-acetoin + NADH + H+

0

-

1.1.1.76

meso-2,3-butanediol + NAD+ = (R,S)-acetoin + NADH + H+

0

-

1.1.1.76

meso-2,3-butanediol + NAD+ = acetoin + NADH

0

-

1.1.1.76

(S,S)-butane-2,3-diol + NAD+ = L-acetoin + NADH + H+

0

-

1.1.1.76

diacetyl + NADH = L-acetoin + NAD+

389573, 389580

-

1.1.1.6

2 entries

1.1.1.76

5 entries

1.1.1.81

2,3-butandione + NAD(P)H = butan-2-ol-3-one + NAD(P)+

287375

-

1.1.1.B20

(2R,3S)-butane-2,3-diol + NAD+ = acetoin + NADH + H+

0

-

1.1.1.B20

meso-2,3-butanediol + NAD+ = acetoin + NADH

0

-

1.1.1.B20

meso-2,3-butanediol + NAD+ = acetoin + NADH + H+

0

-

1.1.1.B20

3 entries

1.1.9.1

2,3-butanediol + ferricyanide = 3-hydroxybutan-2-one + ferrocyanide

0

-

1.13.12.16

1-hydroxybutyl-2-nitronate + O2 = 3-hydroxy-butane-2-one + HNO2

0

-

1.13.12.16

3-nitro-2-butanol + O2 = 3-hydroxy-butane-2-one + HNO2

0

-

1.13.12.16

2 entries

2.2.1.6

2 butane-2,3-dione = acetylacetoin + acetoin

0

-

4.1.1.1

acetaldehyde + acetaldehyde = acetoin

650671

-

4.1.1.1

pyruvate + acetaldehyde = acetoin + CO2

0

-

4.1.1.1

2 entries

4.1.1.5

alpha-acetolactate + CO2 = acetoin

0

-

Inhibitor in Enzyme-catalyzed Reactions (3 results)

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Show Inhibitors (3 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.185

probably all L(+)-alpha-hydroxycarbonyls products inhibit uncompetitively at non-saturated concentrations

286137

-

1.1.1.304

noncompetitive, product inhibition

287026

-

3.5.1.26

competitive inhibition, Ki: 4.1 mM

209062

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (16 results)

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Show Turnover Number (16 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.1

0.2

-

45°C, pH 6.1, cosubstrate: NADPH, wild-type enzyme

744545

1.1.1.1

0.36

-

45°C, pH 6.1, cosubstrate: NADH, wild-type enzyme

744545

1.1.1.1

1.1

-

45°C, pH 6.1, cosubstrate: NADH, mutant enzyme K249G/H255R

744545

1.1.1.1

1.2

-

45°C, pH 6.1, cosubstrate: NADPH, mutant enzyme K249G/H255R

744545

1.1.1.1

13.7

-

pH 6.0, 70°C

735486

1.1.1.10

0.65

-

pH 7.0, 25°C

656049

1.1.1.10

3

-

pH 7.0, 25°C

656049

1.1.1.10

6.9

-

pH 7.0, 25°C

656049

1.1.1.1

5 entries

1.1.1.10

3 entries

1.1.1.149

0.097

-

at pH 7.4 and 37°C

740126

1.1.1.184

183

-

pH 7.5, 37°C

724899

1.1.1.2

142

-

cosubstrate: NADPH, pH 7.5, 80°C

738511

1.1.1.4

0.5

-

cosubstrate NADPH, pH 7.0, temperature not specified in the publication

740952

1.1.1.4

1.4

-

cosubstrate NADH, pH 7.0, temperature not specified in the publication

740952

1.1.1.4

145

-

pH 7.5, 25°C

737501

1.1.1.4

3 entries

1.1.1.71

13.7

-

with NADH as cosubstrate, at pH 6.0 and 70°C

735486

1.1.1.76

6

-

pH 7.0, 30°C

737865

K_M Value (39 results)

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Show KM Value (39 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.1

0.9

-

45°C, pH 6.1, cosubstrate: NADH, wild-type enzyme

744545

1.1.1.1

5

-

45°C, pH 6.1, cosubstrate: NADPH, mutant enzyme K249G/H255R

744545

1.1.1.1

6.5

-

reduction reaction, pH 6.1, 70°C

667266

1.1.1.1

6.7

-

45°C, pH 6.1, cosubstrate: NADPH, wild-type enzyme

744545

1.1.1.1

13

-

45°C, pH 6.1, cosubstrate: NADH, mutant enzyme K249G/H255R

744545

1.1.1.1

30.2

-

pH 6.0, 70°C

735486

1.1.1.10

1.5

-

pH 7.0, 25°C

656049

1.1.1.10

3.3

-

pH 7.0, 25°C

656049

1.1.1.10

6.9

-

pH 7.0, 25°C

656049

1.1.1.10

9

-

pH 7.0, 25°C

656049

1.1.1.10

13

-

pH 7.0, 25°C

656049

1.1.1.149

0.162

-

at pH 7.4 and 37°C

740126

1.1.1.149

0.186

0.272

-

285999

1.1.1.149

0.272

-

-

285999

1.1.1.1

6 entries

1.1.1.10

5 entries

1.1.1.149

3 entries

1.1.1.153

29

-

-

286021

1.1.1.162

13

-

-

286091

1.1.1.184

16

-

pH 7.5, 37°C

724899

1.1.1.185

2.013

-

pI 6.2 form

286134

1.1.1.185

2.164

-

pI 4.8 form

286134

1.1.1.185

2.59

-

pI 7.2 form

286134

1.1.1.185

3 entries

1.1.1.2

0.32

-

cosubstrate: NADPH, pH 7.5, 80°C

738511

1.1.1.4

0.06

-

pH 7.0, 30°C

721872

1.1.1.4

0.2

-

pH 7.0, 30°C

722559

1.1.1.4

0.3

-

pH 8.0, 22°C

721345

1.1.1.4

0.4

-

-

246412

1.1.1.4

0.53

-

-

246407

1.1.1.4

0.84

-

(S)-acetoin, pH 7.0, 30°C

722559

1.1.1.4

3.4

-

cosubstrate NADH, pH 7.0, temperature not specified in the publication

740952

1.1.1.4

4.5

-

-

246409

1.1.1.4

6.5

-

-

667266

1.1.1.4

13.6

-

cosubstrate NADPH, pH 7.0, temperature not specified in the publication

740952

1.1.1.4

71

-

pH 7.5, 25°C

737501

1.1.1.4

11 entries

1.1.1.406

62

-

-

389404

1.1.1.71

30.2

-

with NADH as cosubstrate, at pH 6.0 and 70°C

735486

1.1.1.76

0.44

-

pH 6.0

389580

1.1.1.76

42.2

-

pH 7.0, 30°C

737865

1.1.1.76

2 entries

1.1.1.B20

0.23

-

racemic (R/S)-acetoin, pH 7.0, 30°C, recombinant enzyme

741710

2.3.1.190

0.0028

-

E1 complex, 80°C, pH 7.0

703733

2.3.1.190

0.055

-

pH 7.4, 30°C

756608

2.3.1.190

2 entries

References & Links

Literature References (65)

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Show Reference (65 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

209062

666738

Effect of different compounds on 1-aspartamido-beta-N-acetylglucosamine amidohydrolase from human liver

1978

Dugal, B.

Biochem. J.

171

799-802

246407

25056

Bacterial 2,3-butanediol dehydrogenases

1978

Höhn-Bentz, H.; Radler, F.

Arch. Microbiol.

116

197-203

246408

10389264

Formation of a chiral acetoinic compound from diacetyl by Escherichia coli expressing meso-2,3-butanediol dehydrogenase

1999

Ui, S.; Mimura, A.; Ohkuma, M.; Kudo, T.

Lett. Appl. Microbiol.

28

457-460

246409

11306064

Characterization and functional role of Saccharomyces cerevisiae 2,3-butanediol dehydrogenase

2001

Gonzalez, E.; Fernandez, M.R.; Larroy, C.; Pares, X.; Biosca, J.A.

Chem. Biol. Interact.

130

425-434

246410

2222122

Purification and characterization of a (R)-2,3-butanediol dehydrogenase from Saccharomyces cerevisiae

1990

Heidlas, J.; Tressl, R.

Arch. Microbiol.

154

267-273

246411

16348209

Properties of 2,3-butanediol dehydrogenase from Lactococcus lactis subsp. lactis in relation to citrate fermentation

1990

Crow, V.L.

Appl. Environ. Microbiol.

56

1656-1665

246412

2040298

Purification, characterization and some properties of diacetyl(acetoin) reductase from Enterobacter aerogenes

1991

Carballo, J.; Martin, R.; Bernardo, A.; Gonzalez, J.

Eur. J. Biochem.

198

327-332

246413

10938079

Characterization of a (2R,3R)-2,3-butaendiol dehydrogenase as the Saccharomyces cerevisiae YAL060W gene product

2000

Gonzalez, E.; Fernandez, M.R.; Larroy, C.; Sola, L.; Pericas, M.A.; Pares, X.; Biosca, J.A.

J. Biol. Chem.

275

35876-35885

285735

9214773

Purification and properties of a new enzyme, D-carnitine dehydrogenase from Agrobacterium sp. 525a

1997

Setyahida, S.; Ueyama, T.; Arimoto, T.; Mori, N.; Kitamoto, Y.

Biosci. Biotechnol. Biochem.

61

1055-1058

285999

7484385

Substrate specificity and kinetic mechanism of Tetrahymena 20alpha-hydroxysteroid dehydrogenase

1995

Hara, A.; Inazu, A.; Deyashiki, Y.; Nozawa, Y.

Adv. Exp. Med. Biol.

372

249-258

286020

6200109

Sepiapterin reductase exhibits a NADPH-dependent dicarbonyl reductase activity

1984

Katoh, S.; Sueoka, T.

Biochem. Biophys. Res. Commun.

118

859-866

286021

3904835

Carbonyl reductase activity of sepiapterin reductase from rat erythrocytes

1985

Sueoka, T.; Katoh, S.

Biochim. Biophys. Acta

843

193-198

286040

2621446

Purification and properties of glycerol:NADP+ 2-oxidoreductase from Schizisaccharomyces pombe

1989

Marshall, J.H.; Kong, Y.C.; Sloan, J.; May, J.W.

J. Gen. Microbiol.

135

697-701

286042

4146296

NADP specific dihydroxyacetone reductase from Dunaliella parva

1973

Amotz-Ben, A.; Avron, M.

FEBS Lett.

29

153-155

286091

9538249

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Links to other databases for acetoin

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