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Ligand 2-butanol

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Natural Substrate (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.71

2-butanol + NAD(P)+ = butan-2-one + NAD(P)H + H+

735486

-

1.1.1.80

butan-2-ol + NADP+ = butanone + NADPH + H+

724969

-

1.1.3.18

2-butanol + O2 = butan-2-one + H2O2

724152

-

Substrate in Enzyme-catalyzed Reactions (40 results)

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Show Substrate (40 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

2-butanol + NAD+ = 2-butanone + NADH + H+

760247, 684612, 728012, 668532, 684614, 687850, 695811

-

1.1.1.1

butan-2-ol + NAD+ = butan-2-one + NADH

285619, 285575, 285608, 285602, 285650, 285640, 285647, 285621, 285614, 285639, 285616, 285638, 285652, 285630, 285586

-

1.1.1.1

butan-2-ol + NAD+ = butanone + NADH + H+

736243

-

1.1.1.1

3 entries

1.1.1.16

2-butanol + NAD+ = ? + NADH + H+

740390

-

1.1.1.184

2-butanol + NADP+ = 2-butanone + NADPH + H+

724899

-

1.1.1.2

2-butanol + NADP+ = 2-butanone + NADPH

654493

1bxz, 3D-view

1.1.1.2

2-butanol + NADP+ = 2-butanone + NADPH + H+

738511

1bxz, 3D-view

1.1.1.2

2-butanol + NADP+ = ?

689955

1bxz, 3D-view

1.1.1.2

2-butanol + NADP+ = butan-2-one + NADPH

286191, 286206, 286197, 286209

1bxz, 3D-view

1.1.1.2

2-butanol + NADP+ = butanone + NADPH

654493

1bxz, 3D-view

1.1.1.2

butan-2-ol + NADP+ = butanone + NADPH + H+

735625, 736940

-

1.1.1.2

6 entries

1.1.1.202

2-butanol + NAD+ = NADH + butanone

389496, 389494

-

1.1.1.245

2-butanol + NAD+ = 2-butanone + NADH

286383

-

1.1.1.6

2-butanol + NAD+ = 2-butanone + NADH + H+

747295

-

1.1.1.71

2-butanol + NAD(P)+ = butan-2-one + NAD(P)H + H+

735486

-

1.1.1.71

2-butanol + NADP+ = 2-butanone + NADPH + H+

722208

-

1.1.1.71

2-butanol + NADP+ = butanone + NADPH + H+

728288, 726769

-

1.1.1.71

butan-2-ol + NADP+ = butan-2-one + NADPH + H+

740200

-

1.1.1.71

4 entries

1.1.1.76

2-butanol + NAD+ = 2-butanone + NADH + H+

756608, 721396

-

1.1.1.80

butan-2-ol + NADP+ = butanone + NADPH + H+

724969

-

1.1.1.B4

2-butanol + NAD+ = 2-butanone + NADH

687864

-

1.1.2.9

2-butanol + ferricytochrome c = 2-butanone + ferrocytochrome c + H+

688853

-

1.1.3.13

2-butanol + O2 = 2-butanone + H2O2

484925

-

1.1.3.18

2-butanol + O2 = 2-butanone + H2O2

348181, 287626, 348175, 348177

-

1.1.3.18

2-butanol + O2 = butan-2-one + H2O2

724152

-

1.1.3.30

2-butanol + O2 = 2-butanone + H2O2

287626

-

1.1.3.30

3-butanol + O2 = 3-butanone + H2O2

287626

-

1.1.5.11

2-butanol + a quinone = 2-butanone + a quinol

738514

-

1.1.5.11

butan-2-ol + a quinone = 2-butanone + a quinol

687366

-

1.1.3.18

2 entries

1.1.3.30

2 entries

1.1.5.11

2 entries

1.1.5.5

2-butanol + ubiquinone = 2-butanone + ubiquinol

725298

-

1.1.5.7

2-butanol + pyrroloquinoline quinone = butane-2-one + reduced pyrroloquinoline quinone

696803

-

1.1.9.1

2-butanol + ferricyanide = butanone + ferrocyanide

705187, 687362

-

1.1.9.1

2-butanol + ferrocyanide = butanone + ferricyanide

701774

-

1.1.9.1

2 entries

1.1.99.12

2-butanol + acceptor = 2-butanone + reduced acceptor

287728

-

1.1.99.36

2-butanol + N,N-dimethyl-4-nitrosoaniline = butanone + 4-(hydroxylamino)-N,N-dimethylaniline

708364

-

2.8.2.22

4-nitrophenyl sulfate + 2-butanol = 4-nitrophenol + 2-butyl sulfate

723897

-

3.1.1.3

isophthalate + 2-butanol = isophthalic acid mono(1-methylpropyl)ester + isophthalic acid di(1-methylpropyl)ester + H2O

693692

-

3.2.1.52

di-N-acetylchitobiose + 2-butanol = ?

655769

-

3.4.21.63

N-Cbz-L-Asp + sec-butanol = N-Cbz-L-Asp-sec-butyl ester

650680

-

3.4.21.63

N-Cbz-L-Tyr + sec-butanol = N-Cbz-L-Tyr-sec-butyl ester

650680

-

3.4.21.63

2 entries

Product in Enzyme-catalyzed Reactions (27 results)

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Show Product (27 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

2-butanone + NADH + H+ = 2-butanol + NAD+

-

-

1.1.1.1

2-butanone + NADH + H+ = butan-2-ol + NAD+

-

-

1.1.1.1

2-butanone + NADPH + H+ = butan-2-ol + NADP+

-

-

1.1.1.1

butan-2-one + NADH = butan-2-ol + NAD+

285586,

-

1.1.1.1

4 entries

1.1.1.184

2-butanone + NADPH = 2-butanol + NADP+

-

-

1.1.1.2

2-butanone + NADP+ = 2-butanol + NADPH + H+

-

1bxz, 3D-view

1.1.1.2

2-butanone + NADPH + H+ = 2-butanol + NADP+

-

1bxz, 3D-view

1.1.1.2

butanone + NADPH + H+ = butan-2-ol + NADP+

-

-

1.1.1.4

2-butanone + NADP+ = 2-butanol + NADPH + H+

-

-

1.1.1.4

butanone + NADPH + H+ = butan-2-ol + NADP+

-

-

1.1.1.2

3 entries

1.1.1.4

2 entries

1.1.1.71

butan-2-one + NADPH + H+ = butan-2-ol + NADP+

-

-

1.1.1.73

butan-2-one + NADH + H+ = butan-2-ol + NAD+

-

-

1.1.1.80

2-butanone + NADPH + H+ = 2-butanol + NADP+

-

-

1.1.1.80

butanone + NADPH + H+ = butan-2-ol + NADP+

-

-

1.1.1.B4

2-butanone + NAD+ = 2-butanol + NADH + H+

-

-

1.1.1.B4

2-butanone + NADH = 2-butanol + NAD+

-

-

1.1.1.80

2 entries

1.1.1.B4

2 entries

1.1.98.5

2-butanone + reduced coenzyme F420 = 2-butanol + oxidized coenzyme F420

-

-

1.14.13.230

butane + NADH + H+ + O2 = butan-2-ol + NAD+ + H2O

-

-

1.14.13.25

butane + NAD(P)H + O2 = 1-butanol + 2-butanol + NAD(P)+ + H2O

438920, , 438947

-

1.14.18.3

2 butane + 2 reduced acceptor + 2 H+ + 2 O2 = 1-butanol + 2-butanol + 2 acceptor + 2 H2O

-

-

1.14.18.3

butane + duroquinol + O2 = 2-butanol + butanal + duroquinone + H2O

-

-

1.14.18.3

n-butane + reduced acceptor + O2 = 2-butanol + acceptor + H2O

-

-

1.14.18.3

3 entries

3.1.1.1

sec-butyl acetate + H2O = sec-butanol + acetate

-

-

3.1.1.73

2-butyl ferulate + H2O = ferulic acid + 2-butanol

-

-

3.8.1.5

2-bromobutane + H2O = 2-butanol + bromide

-

-

3.8.1.5

2-chlorobutane + H2O = 2-butanol + chloride

-

-

3.8.1.5

2-iodobutane + H2O = 2-butanol + iodide

-

-

3.8.1.5

3 entries

Activator in Enzyme-catalyzed Reactions (4 results)

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Show Activating Compound (4 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.7.1.30

activates

641299

-

3.1.1.3

2-butanol enhances lipase activity

693692

-

3.2.1.21

3fold activation

677741

-

4.6.1.1

isoform AC6 shows about 60% stimulation of activity with 100 mM 2-butanol, isoform AC7 shows about 70% stimulation of activity with 100 mM 2-butanol, isoform AC9 shows about 60% stimulation of activity with 100 mM 2-butanol

713708

-

Inhibitor in Enzyme-catalyzed Reactions (7 results)

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Show Inhibitors (7 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.99.36

substrate inhibition

708364

-

2.3.1.20

-

486485

-

3.1.1.1

10% (v/v), 52% inhibition; 10% (w/v), 42% inhibition

724578

-

3.1.1.6

-

35233

-

3.2.1.21

highest decrease of activity in comparison to ethanol and 2-propanol

326283

-

3.4.24.23

-

668007

-

3.4.24.27

-

651799, 668007

-

3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (2 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.1.1.2

1bxz, 3D-view

2.7.11.1

4ejn, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (8 results)

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Show Turnover Number (8 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.1

0.31

-

mutant enzyme W54L

285647

1.1.1.1

0.48

-

pH 8.0, 60°C

728012

1.1.1.1

3.55

-

-

285621

1.1.1.1

4.75

-

-

285602

1.1.1.1

11.9

-

wild-type enzyme Adh 1

285647

1.1.1.1

5 entries

1.1.1.184

149

-

pH 7.5, 37°C

724899

1.1.1.2

833

-

cosubstrate: NADP+, pH 7.5, 80°C

738511

1.1.98.5

49

-

pH 5.8, 37°C

724899

K_M Value (24 results)

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Show KM Value (24 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.1

0.35

-

-

285621

1.1.1.1

0.41

-

-

285619

1.1.1.1

0.86

-

-

285619

1.1.1.1

1.05

-

pH 8.0, 60°C

728012

1.1.1.1

1.6

-

-

285619

1.1.1.1

11.9

-

33°C, pH 8

684612

1.1.1.1

93.3

-

wilde-type enzyme ADh1

285647

1.1.1.1

7 entries

1.1.1.184

3.5

-

pH 7.5, 37°C

724899

1.1.1.2

0.31

-

pH 7.8, 40°C

735625

1.1.1.2

0.38

-

cosubstrate: NADP+, pH 7.5, 80°C

738511

1.1.1.2

0.51

-

2° Adh

286197

1.1.1.2

7

-

r-TBADH, wild-type, mutant D150C-TBADH

286201

1.1.1.2

7.17

-

mutant H59Q-TBADH

286201

1.1.1.2

9.2

-

mutant C37A-TBADH

286201

1.1.1.2

170

-

-

286206

1.1.1.2

7 entries

1.1.1.6

0.3

-

pH and temperature not specified in the publication

747295

1.1.1.80

0.00078

-

37°C, pH 9.0

724969

1.1.1.B4

0.065

-

pH 8.5, 30°C

687864

1.1.5.11

0.662

-

at pH 7.0 and 30°C

738514

1.1.9.1

8

-

pH 7.5, 25°C

705187

1.1.9.1

8

-

soluble enzyme, pH 7.7, presence of CaCl2

701774

1.1.9.1

12

-

enzyme electrode, pH 7.7, presence of CaCl2

701774

1.1.9.1

3 entries

1.1.98.5

1.2

-

pH 5.8, 37°C

724899

1.1.99.36

10.1

-

pH 7.0, 45°C

708364

K_i Value (4 results)

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Show KI Value (4 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.99.36

4.4

-

pH 7.0, 45°C

708364

3.4.24.23

11700

-

pH 7.5, 25°C

668007

3.4.24.27

40

-

pH 7.5, 25°C

651799

3.4.24.27

370

-

pH 7.5, 25°C

668007

3.4.24.27

2 entries

References & Links

Literature References (79)

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Show Reference (79 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

35233

4436255

Purification and characterization of the nocardial acetylesterase involved in 2-butanone degradation

1974

Eubanks, E.F.; Forney, F.W.; Larson, A.D.

J. Bacteriol.

120

1133-1143

285575

2819035

Purification and steady-state kinetic characterization of human liver beta 3 beta 3 alcohol dehydrogenase

1989

Burnell, J.C.; Li, T.K.; Bosron, W.F.

Biochemistry

28

6810-6815

285586

1935957

Substrate specificity and stereoselectivity of horse liver alcohol dehydrogenase. Kinetic evaluation of binding and activation parameters controlling the catalytic cycles of unbranched, acyclic secondary alcohols and ketones as substrates of the native and active-site-specific Co(II)-substituted enzyme

1991

Adolph, H.W.; Maurer, P.; Schneider-Bernloehr, H.; Sartorius, C.; Zeppezauer, M.

Eur. J. Biochem.

201

615-625

285602

3178842

A genuine organ specific alcohol dehydrogenase from hamster testes: isolation, characterization and developmental changes

1988

Keung, W.M.

Biochem. Biophys. Res. Commun.

156

38-45

285608

7876099

Expression and kinetic characterization of recombinant human stomach alcohol dehydrogenase. Active-site amino acid sequence explains substrate specificity copared with liver isozymes

1995

Kedishvili, N.Y.; Bosron, W.F.; Stone, C.L.; Hurley, T.D.; Peggs, C.F.; Thomasson, H.R.; Popov, K.M.; Carr, L.G.; Edenberg, H.J.; Li, T.K.

J. Biol. Chem.

270

3625-3630

285614

640168

Purification and properties of an alcohol dehydrogenase from the liver and intestinal caecum of rainbow trout (Salmo gairdnerii)

1978

Bauermeister, A.; Sargent, J.

Biochem. Soc. Trans.

6

222-224

285616

2943270

Biochemical properties of alcohol dehydrogenase from Drosophila lebanonensis

1986

Winberg, J.O.; Hovik, R.; McKinley-McKee, J.S.; Juan, E.; Gonzalez-Duarte, R.

Biochem. J.

235

481-490

285619

6796069

Determination of some biochemical and structural features of alcohol dehydrogenases from Drosophila simulans and Drosophila virilis. Comparison of their properties with the Drosophila melanogaster Adhs enzyme

1981

Juan, E.; Gonzalez-Duarte, R.

Biochem. J.

195

61-69

285621

3115775

A novel archaebacterial NAD+-dependent alcohol dehydrogenase. Purification and properties

1987

Rella, R.; Raia, C.A.; Pensa, M.; Pisani, F.M.; Gambacorta, A.; de Rosa, M.; Rossi, M.

Eur. J. Biochem.

167

475-479

285630

-

Purification and characterization of three non-allelic alcohol dehydrogenase isoenzymes in maize

1982

Lai, Y.K.; Chandlee, J.M.; Scandalios, J.G.

Biochim. Biophys. Acta

706

9-18

285638

4455216

The partial purification and characterization of cytosol alcohol dehydrogenase from Astasia

1974

Morosoli, R.; Begin-Heick, N.

Biochem. J.

141

469-475

285639

-

Purification and properties of an alcohol dehydrogenase from Sporotrichum pulverulentum

1986

Rudge, J.; Bickerstaff, G.F.

Enzyme Microb. Technol.

8

120-124

285640

-

Purification and properties of alcohol dehydrogenase from a mutant strain of Candida guilliermondii

1992

Indrati, R.; Ohita, Y.

Can. J. Microbiol.

38

953-957

285647

8532667

Engineering yeast alcohol dehydrogenase. Replacing Trp54 by Leu broadens substrate specificity

1995

Weinhold, E.G.; Benner, S.A.

Protein Eng.

8

457-461

285650

8730210

Isolation and characterization of three alcohol dehydrogenase isozymes from Syrian golden hamster

1996

Keung, W.M.

Alcohol. Clin. Exp. Res.

20

213-220

285652

8166623

Characterization of mutation-induced changes in the maize (Zea mays L.) ADH1-1S1108 alcohol dehydrogenase

1993

Osterman, J.C.; Chiang, Y.; Markwell, J.

Biochem. Genet.

31

497-506

286191

-

Purification and properties of primary and secondary alcohol dehydrogenases from Thermoanaerobacter ethanolicus

1988

Bryant, F.O.; Wiegel, J.; Ljungdahl, L.G.

Appl. Environ. Microbiol.

2

460-465

286197

8068002

Purification of acetaldehyde dehydrogenase and alcohol dehydrogenases from Thermoanaerobacter ethanolicus 39E and characterization of the secondary-alcohol dehydrogenase (2 degrees Adh) as a bifunctional alcohol dehydrogenase-acetyl-CoA reductive thioesterase

1994

Burdette, D.; Zeikus, J.G.

Biochem. J.

302

163-170

286201

9041649

Thermoanaerobacter brockii alcohol dehydrogenase: characterization of the active site metal and its ligand amino acids

1997

Bogin, O.; Peretz, M.; Burstein, Y.

Protein Sci.

6

450-458

286206

10473548

Structural and enzymatic properties of a gastric NADP(H)-dependent and retinal-active alcohol dehydrogenase

1999

Peralba, J.M.; Cederlund, E.; Crosas, B.; Moreno, A.; Julia, P.; Martinez, S.E.; Persson, B.; Farr s, J.; Pares, X.; Jornvall, H.

J. Biol. Chem.

274

26021-26026

286209

10651277

Crystal structure of a thermophilic alcohol dehydrogenase substrate complex suggests determinants of substrate specificity and thermostability

1999

Li, C.; Heatwole, J.; Soelaiman, S.; Shoham, M.

Proteins

37

619-627

286383

-

Purification and characterization of a cyclohexanol dehydrogenase from Rhodococcus sp. TK6

2002

Tae-Kang, K.; Choi, J.H.; Rhee, I.K.

J. Microbiol. Biotechnol.

12

39-45

287626

-

Purification and properties of polyvinyl alcohol oxidase with broad substrate range obtained from Pseudomonas vesicularis var. povalolyticus PH

1997

Kawagoshi, Y.; Fujita, M.

World J. Microbiol. Biotechnol.

13

273-277

287728

27392874

Isolation and Characterization of a New Quinoprotein Dehydrogenase, L-Sorbose/L-Sorbosone Dehydrogenase.

1999

Asakura, A.; Hoshino, T.

Biosci. Biotechnol. Biochem.

63

46-53

326283

8987723

Properties of an intracellular beta-glucosidase purified from the cellobiose-fermenting yeast Candida wickerhamii

1996

Skory, C.D.; Freer, S.N.; Bothast, R.J.

Appl. Microbiol. Biotechnol.

546

353-359

348175

-

A secondary alcohol oxidase: a component of a polyvinyl alcohol degrading enzyme preparation

1977

Morita, M.; Watanabe, Y.

Agric. Biol. Chem.

41

1535-1537

348177

-

Purification and properties of secondary alcohol oxidase from a strain of Pseudomonas

1979

Morita, M.; Hamada, N.; Sakai, K.; Watanabe, Y.

Agric. Biol. Chem.

43

1225-1235

348181

-

Purification and properties of secondary alcohol oxidase with an acidic isoelectric point

1985

Sakai, K.; Hamada, N.; Watanabe, Y.

Agric. Biol. Chem.

49

817-825

389494

7721705

Purification of 1,3-propanediol dehydrogenase from Citrobacter freundii and cloning, sequencing, and overexpression of the corresponding gene in Escherichia coli

1995

Daniel, R.; Boenigk, R.; Gottschalk, G.

J. Bacteriol.

177

2151-2156

389496

10938419

Purification and characterization of the 1,3-propanediol dehydrogenase of Clostridium butyricum E5

2000

Malaoui, H.; Marczak, R.

Enzyme Microb. Technol.

27

399-405

438920

411486

The soluble methane mono-oxygenase of Methylococcus capsulatus (Bath). Its ability to oxygenate n-alkanes, n-alkenes, ethers, and alicyclic, aromatic and heterocyclic compounds

1977

Colby, J.; Stirling, D.I.; Dalton, H.

Biochem. J.

165

395-402

438947

10473397

Purification and characterization of the soluble methane monooxygenase of the type II methanotrophic bacterium Methylocystis sp. strain WI 14

1999

Grosse, S.; Laramee, L.; Wendlandt, K.D.; McDonald, I.R.; Miguez, C.B.; Kleber, H.P.

Appl. Environ. Microbiol.

65

3929-3935

484925

9142745

Purification and properties of alcohol oxidase from Candida methanosorbosa M-2003

1997

Suye, S.

Curr. Microbiol.

34

374-377

486485

947894

Triacylglycerol synthesis in isolated fat cells. Studies on the microsomal diacylglycerol acyltransferase activity using ethanol-dispersed diacylglycerols

1976

Coleman, R.A.; Bell, R.M.

J. Biol. Chem.

251

4537-4543

641299

238627

Activation of bovine liver glycerol kinase by ethanol

1975

Schneider, P.B.

Biochim. Biophys. Acta

397

110-116

650680

-

Enzymes catalyzed esterification of N-protcted amino acids with secondary alcohol

1997

Shih, I.L.; Chiu, L.C.; Lai, C.T.; Liaw, W.C.; Tai, D.F.

Biotechnol. Lett.

19

857-859

651799

12473197

Inhibitory effects of alcohols on thermolysin activity as examined using a fluorescent substrate

2002

Muta, Y.; Inouye, K.

J. Biochem.

132

945-951

654493

11742541

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Links to other databases for 2-butanol

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