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Ligand 3-buten-2-one

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Product in Enzyme-catalyzed Reactions (4 results)

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Show Natural Product (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.58

(3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2 = (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O

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-

1.14.14.58

(3S,6E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2 = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O

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-

1.14.14.58

(E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2 = 4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O

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-

1.14.14.58

(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2 = (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O

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-

1.14.14.58

4 entries

Substrate in Enzyme-catalyzed Reactions (14 results)

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Show Substrate (14 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.27

3-buten-2-one + NADPH + H+ = butan-2-one + NADP+

724703

-

1.3.1.31

but-3-en-2-one + NADPH = butan-2-one + NADP+

684248

-

1.3.1.48

methyl vinyl ketone + NADPH = ?

690204

-

1.3.1.48

trans-methylvinylketone + NAD(P)H = butane-2-one + NAD(P)+

390826, 390830

-

1.3.1.74

3-buten-2-one + NAD(P)H = 2-butanone + NAD(P)+

636484

-

1.3.1.74

3-buten-2-one + NADH = 2-butanone + NAD+

725462

-

1.3.1.74

3-buten-2-one + NADPH = 2-butanone + NADP+

725462

-

1.3.1.74

methyl vinyl ketone + NAD(P)H = dimethylketone + NAD(P)+

390830

-

1.3.1.95

3-buten-2-one + NADH + H+ = ?

697707

-

1.3.1.95

methyl vinyl ketone + methyl viologen = ?

696519

-

1.3.1.48

2 entries

1.3.1.74

4 entries

1.3.1.95

2 entries

1.6.5.5

3-buten-2-one + NADPH = 2-butanone + NADP+

724703

-

2.2.1.12

pyruvate + but-3-en-2-one = hexane-2,5-dione + CO2

729088

-

4.1.2.46

cyanide + methyl vinyl ketone = (2R)-2-hydroxy-2-methyl-3-butenenitrile

5143

-

4.1.2.46

cyanide + methyl vinyl ketone = (2R)-2-hydroxy-2-methylbut-3-enenitrile

706342

-

4.1.2.46

2 entries

Product in Enzyme-catalyzed Reactions (7 results)

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Show Product (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.165

1-butene-3-ol + NAD+ = 1-buten-3-one + NADH

286099

-

1.14.14.58

(3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2 = (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O

-

-

1.14.14.58

(3S,6E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2 = (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O

-

-

1.14.14.58

(E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2 = 4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O

-

-

1.14.14.58

(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2 = (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O

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-

1.14.14.58

(6E,10E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2 = (3E,7E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + [oxidized NADPH-hemoprotein reductase] + but-3-en-2-one + 2 H2O

-

-

1.14.14.58

5 entries

1.14.14.59

(3S,6E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2 = (3E)-4,8-dimethylnona-1,3,7-triene + [oxidized NADPH-hemoprotein reductase] + but-3-en-2-one + 2 H2O

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-

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.184

74% inhibition at 10 mM

655017

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (9 results)

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Show Turnover Number (9 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.3.1.27

0.167

-

wild-type, pH 7.5, temperature not specified in the publication

724703

1.3.1.48

156

-

-

390830

1.3.1.74

1.38

-

pH 6

636484

1.3.1.74

3.5

-

pH 7.0, 25°C

725462

1.3.1.74

74

-

pH 7.0, 25°C

725462

1.3.1.74

3 entries

1.3.1.95

29

-

in 50 mM Tris/HCl, pH 7.0, at 25°C

697707

1.6.5.5

0.16

-

pH 7, 25°C, wild-type

724703

1.6.5.5

0.28

-

pH 7, 25°C, mutant T59F

724703

1.6.5.5

0.97

-

pH 7, 25°C, mutant T53F

724703

1.6.5.5

3 entries

K_M Value (10 results)

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Show KM Value (10 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.3.1.27

0.035

-

wild-type, pH 7.5, temperature not specified in the publication

724703

1.3.1.48

0.1289

-

in 100 mM phosphate buffer (pH 7.4), at 25°C

690204

1.3.1.48

0.58

-

-

390830

1.3.1.74

0.055

-

pH 6

636484

1.3.1.74

0.13

-

pH 7.0, 25°C

725462

1.3.1.74

2.88

-

pH 7.0, 25°C

725462

1.3.1.48

2 entries

1.3.1.74

3 entries

1.3.1.95

1.8

-

apparent value, in 50 mM Tris/HCl, pH 7.0, at 25°C

697707

1.6.5.5

0.035

-

pH 7, 25°C, wild-type

724703

1.6.5.5

0.06

-

pH 7, 25°C, mutant T59F

724703

1.6.5.5

0.13

-

pH 7, 25°C, mutant T53F

724703

1.6.5.5

3 entries

References & Links

Literature References (14)

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Show Reference (14 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

5143

8387315

Improved purification of an (R)-oxynitrilase from Linum usitatissimum (flax) and investigation of the substrate range

1993

Albrecht, J.; Jansen, I.; Kula, M.R.

Biotechnol. Appl. Biochem.

17

191-203

286099

-

Purification and characterization of 2-alkyne-1-ol dehydrogenase induced by 2-butyne-1,4-diol in Fusarium merismoides B11

1974

Miyoshi, T.; Sato, H.; Harada, T.

Biochim. Biophys. Acta

358

231-239

390826

7693121

Purification of a 15-ketoprostaglandin DELTA13-reductase from rat liver and its ability to reduce the double bond of xenobiotics

1993

Kitamura, S.; Katsura, H.; Tatsumi, K.

Biochem. Mol. Biol. Int.

30

839-847

390830

11524419

Antioxidative function and substrate specificity of NAD(P)H-dependent alkenal/one oxidoreductase. A new role for leukotriene B4 12-hydroxydehydrogenase/15-oxoprostaglandin 13-reductase

2001

Dick, R.A.; Kwak, M.K.; Sutter, T.R.; Kensler, T.W.

J. Biol. Chem.

276

40803-40810

636484

12514241

The NADPH:quinone oxidoreductase P1-x-crystallin in Arabidopsis catalyzes the alpha,beta-hydrogenation of 2-alkenals: Detoxication of the lipid peroxide-derived reactive aldehydes

2002

Mano, J.i.; Torii, Y.; Hayashi, S.i.; Takimoto, K.; Matsui, K.; Nakamura, K.; Inze, D.; Babiychuk, E.; Kushnir, S.; Asada, K.

Plant Cell Physiol.

43

1445-1455

655017

12353647

Purification and properties of a carbonyl reductase useful for production of ethyl (S)-4-chloro-3-hydroxybutanoate from Kluyveromyces lactis

2002

Yamamoto, H.; Kimoto, N.; Matsuyama, A.; Kobayashi, Y.

Biosci. Biotechnol. Biochem.

66

1775-1778

684248

-

Comparison of three enoate reductases and their potential use for biotransformations

2007

Chaparro-Riggers, J.F.; Rogers, T.A.; Vazquez-Figueroa, E.; Polizzi, K.M.; Bommarius, A.S.

Adv. Synth. Catal.

349

1521-1531

690204

18274955

Leukotriene B4 12-hydroxydehydrogenase/15-ketoprostaglandin DELTA13-reductase (LTB4 12-HD/PGR) responsible for the reduction of a double-bond of the alpha,beta-unsaturated ketone of an aryl propionic acid non-steroidal anti-inflammatory agent CS-670

2008

Itoh, K.; Yamamoto, K.; Adachi, M.; Kosaka, T.; Tanaka, Y.

Xenobiotica

38

249-263

696519

4063066

Purification and some properties of an acryloyl-CoA reductase of Clostridium kluyveri

1985

Sedlmeier, H.; Simon, H.

Biol. Chem. Hoppe-Seyler

366

953-961

697707

12603323

Acryloyl-CoA reductase from Clostridium propionicum: An enzyme complex of propionyl-CoA dehydrogenase and electron-transferring flavoprotein

2003

Hetzel, M.; Brock, M.; Selmer, T.; Pierik, A.; Golding, B.; Buckel, W.

Eur. J. Biochem.

270

902-910

706342

-

Expression of the Zn2+-containing hydroxynitrile lyase from flax (Linum usitatissimum) in Pichia pastoris - utilization of the recombinant enzyme for enzymatic analysis and site-directed mutagenesis

1998

Trummler, K.; Roos, J.; Schwaneberg, U.; Effenberger, F.; Förster, S.; Pfizenmaier, K.; Wajant, H.

Plant Sci.

139

19-27

724703

20835842

Kinetic and structural evidence of the alkenal/one reductase specificity of human zeta-crystallin

2011

Porte, S.; Moeini, A.; Reche, I.; Shafqat, N.; Oppermann, U.; Farres, J.; Pares, X.

Cell. Mol. Life Sci.

68

1065-1077

725462

21169366

NADPH-dependent reductases involved in the detoxification of reactive carbonyls in plants

2011

Yamauchi, Y.; Hasegawa, A.; Taninaka, A.; Mizutani, M.; Sugimoto, Y.

J. Biol. Chem.

286

6999-7009

729088

24957249

Asymmetric Stetter reactions catalyzed by thiamine diphosphate-dependent enzymes

2014

Kasparyan, E.; Richter, M.; Dresen, C.; Walter, L.S.; Fuchs, G.; Leeper, F.J.; Wacker, T.; Andrade, S.L.; Kolter, G.; Pohl, M.; Mueller, M.

Appl. Microbiol. Biotechnol.

98

9681-9690

Links to other databases for 3-buten-2-one

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Show Links (1 entry)

ChEBI

PubChem

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