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Ligand dodecanal

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

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Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.2

lauryl aldehyde + NADPH = lauryl alcohol + NADP+

286184

-

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.3.20

1-dodecanol + O2 = dodecanal + H2O2

0

-

1.2.1.42

dodecanoyl-CoA + NADPH + H+ = dodecanal + CoA + NADP+

0

-

Substrate in Enzyme-catalyzed Reactions (30 results)

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Show Substrate (30 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.192

dodecanal + NAD+ + H+ = dodecanoic acid + NADH

712962

-

1.1.1.2

dodecanal + NADP+ = dodecan-1-ol + NADPH + H+

763448

-

1.1.1.2

dodecanal + NADPH = dodecanol + NADP+

695771

-

1.1.1.2

lauryl aldehyde + NADPH = lauryl alcohol + NADP+

286181, 286184

-

1.1.1.2

n-dodecanal + NADPH + H+ = n-dodecanol + NADP+

286183, 286210

-

1.1.1.2

4 entries

1.1.1.21

1-dodecanal + NADPH + H+ = dodecanol + NADP+

695881

-

1.1.1.71

dodecanal + NAD(P)H = dodecan-1-ol + NAD(P)+

287282

-

1.1.1.72

dodecanal + NADPH + H+ = dodecanol + NADP+

711743

-

1.1.1.90

dodecanal + NADH + H+ = dodecanol + NAD+

724027

-

1.14.14.3

dodecanal + FMNH + O2 = dodecanoic acid + FMN + H2O + light

348578, 348550, 348560, 348580, 348582, 348585, 348587, 348596, 348556, 348586, 348590, 348591, 348593, 348561, 704579, 348545, 348546, 348547, 348548, 348549, 348551, 348552, 348553, 348554, 348555, 348557, 348558, 348559, 348562, 348564, 348565, 348566, 348567, 348568, 348569, 348570, 348571, 348572, 348573, 348574, 348575, 348576, 348577, 348579, 348581, 348583, 348584, 348588, 348589, 348597, 348599, 348600, 348601, 348602, 348604, 348607, 348608, 348543, 348598, 348544, 348563, 348542, 348592, 348594, 348595, 702318

-

1.14.14.3

dodecanal + FMNH2 + O2 = dodecanoate + FMN + H2O + hn

744492, 657939, 658060

-

1.14.14.3

dodecanal + FMNH2 + O2 = dodecanoic acid + FMN + H2O + hv

726677, 726679

-

1.14.14.3

dodecyl aldehyde + FMNH + O2 = ?

702496

-

1.2.1.3

dodecanal + NAD+ + H2O = dodecanoate + NADH

348706

-

1.2.1.3

dodecanal + NAD+ + H2O = dodecanoate + NADH + H+

724222

-

1.2.1.3

dodecanaldehyde + NAD+ + H2O = dodecanoate + NADH + H+

712957

-

1.14.14.3

4 entries

1.2.1.3

3 entries

1.2.1.4

dodecanal + NADP+ + H2O = dodecanoate + NADPH + H+

348725

-

1.2.1.48

dodecanal + NAD+ + H2O = dodecanoate + NADH + 2 H+

762634

-

1.2.1.48

dodecanal + NAD+ + H2O = dodecanoic acid + NADH

390324, 94404, 390320, 389732

-

1.2.1.48

dodecanal + NAD+ + H2O = dodecanoic acid + NADH + H+

693389, 697840

-

1.2.1.5

dodecanal + NADP+ + H2O = dodecanoate + NADPH + H+

348787

-

1.2.1.5

n-dodecanal + NADP+ + H2O = n-dodecanoate + NADPH + H+

671511

-

1.2.1.48

3 entries

1.2.1.5

2 entries

1.2.1.84

dodecanal + NADPH + H+ = dodecanol + NADP+

762636

-

1.2.3.1

dodecyl aldehyde + H2O + O2 = dodecanoic acid + H2O2

741208

-

1.2.5.2

dodecanal + a quinone + H2O = dodecanoate + a quinol

288472

-

4.1.2.10

HCN + dodecanal = (R)-2-hydroxytridecanenitrile

663419

-

4.1.2.47

cyanide + dodecanal = (2S)-2-hydroxytridecanenitrile

650854

-

4.1.2.47

HCN + dodecanal = (S)-2-hydroxytridecanenitrile

663419

-

4.1.99.5

dodecanal + O2 + 2 NADH + 2 H+ = undecane + formate + H2O + 2 NAD+

726552

-

4.1.99.5

n-dodecanal + O2 + 2 NADPH + 2 H+ = undecane + formate + H2O + 2 NADP+

747351

-

4.1.2.47

2 entries

4.1.99.5

2 entries

Product in Enzyme-catalyzed Reactions (25 results)

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Show Product (25 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

1-dodecanol + NAD+ = dodecanal + NADH

0

-

1.1.1.1

dodecan-1-ol + NAD+ = dodecanal + NADH + H+

0

-

1.1.1.1

dodecanol + NAD+ = dodecanal + NADH + H+

0

-

1.1.1.1

3 entries

1.1.1.2

dodecan-1-ol + NADP+ = dodecanal + NADPH + H+

0

-

1.1.1.245

1-decanol + NAD+ = dodecanal + NADH

0

-

1.1.1.245

1-dodecanol + NAD+ = dodecanal + NADH

0

-

1.1.1.245

2 entries

1.1.1.71

dodecan-1-ol + NADP+ = dodecanal + NADPH

287277

-

1.1.3.13

dodecanol + O2 = dodecanal + H2O2

0

-

1.1.3.13

n-dodecanol + O2 = n-dodecanal + H2O2

0

-

1.1.3.20

1-dodecanol + O2 = dodecanal + H2O2

0

-

1.1.3.20

dodecan-1-ol + O2 = dodecanal + H2O2

0

-

1.1.3.20

dodecanol + O2 = dodecanal + H2O2

0, 389734, 389732

-

1.1.3.13

2 entries

1.1.3.20

3 entries

1.1.99.20

1-dodecanol + acceptor = n-dodecanal + reduced acceptor

389904, 389908

-

1.14.11.77

dodecyl sulfate + 2-oxoglutarate + O2 = dodecanal + succinate + CO2 + sulfate

0

-

1.2.1.30

dodecanoate + NADPH + H+ + ATP = dodecanal + NADP+ + AMP + diphosphate

0

-

1.2.1.30

lauric acid + ATP + NADPH + H+ = lauraldehyde + AMP + diphosphate + NADP+

0

-

1.2.1.42

dodecanoyl-CoA + NAD(P)H = dodecanal + NAD(P)+

288215

-

1.2.1.42

dodecanoyl-CoA + NADPH + H+ = dodecanal + CoA + NADP+

0

-

1.2.1.50

lauroyl-CoA + NADP+ = dodecanal + CoA + NADPH

0

-

1.2.1.50

lauroyl-CoA + NADPH + H+ = dodecanal + CoA + NADP+

0

-

1.2.1.30

2 entries

1.2.1.42

2 entries

1.2.1.50

2 entries

1.2.1.84

lauroyl-CoA + 2 NADPH + 2 H+ = dodecanal + CoA + 2 NADP+

0

-

1.2.1.B25

dodecanoyl-CoA + NADPH = dodecanal + CoA + NADP+

0

-

1.3.1.27

trans-2-dodecenal + NAD(P)H = dodecanal + NAD(P)+

390627

-

1.3.1.48

trans-2-dodecenal + NADPH = dodecanal + NADP+

390830

-

1.4.9.1

12-aminododecane + acceptor + H2O = dodecanal + NH3 + reduced acceptor

0

-

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.6.3.1

reversible

636497

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (2 results)

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Show Turnover Number (2 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.21

1.25

-

in 0.1 M potassium phosphate, pH 7.4, at 25°C

695881

1.2.1.48

2.23

-

-

693389

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

1.1.1.2

0.019

-

enzyme from brain

286183

1.1.1.2

0.02

-

enzyme from liver and kidney

286183

1.1.1.2

0.31

-

AR2

286181

1.1.1.2

3 entries

1.1.1.21

0.0026

-

in 0.1 M potassium phosphate, pH 7.4, at 25°C

695881

1.2.1.3

0.005

-

in 100 mM sodium diphosphate, at pH 8.0 and 22°C

724222

1.2.1.3

0.02

-

microsomal enzyme

348706

1.2.1.3

2 entries

1.2.1.4

0.01

-

-

348725

1.2.1.48

0.0136

-

-

693389

1.2.1.48

0.019

-

-

390324

1.2.1.48

2 entries

1.2.1.5

0.137

-

50 mM potassium phosphate buffer pH8.0, 1 mM CaCl2, 36°C

671511

References & Links

Literature References (111)

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Show Reference (111 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

94404

-

Enzymes of wax ester catabolism in jojoba

1981

Moreau, R.A.; Huang, A.H.C.

Methods Enzymol.

71

804-813

286181

6753936

Purification and properties of human liver aldehyde reductases

1982

Petrash, J.M.; Srivastava, S.K.

Biochim. Biophys. Acta

707

105-114

286183

6416297

Purification and properties of an NADPH-linked aldehyde reductase from rat kidney

1983

Takahashi, N.; Saito, T.; Tomita, K.

Biochim. Biophys. Acta

748

444-452

286184

6343086

Isolation and characterization of multiforms of aldehyde reductase in chicken kidney

1983

Hara, A.; Deyashiki, Y.; Nakayama, T.; Sawada, H.

Eur. J. Biochem.

133

207-214

286210

11097895

Thermostable NADP(+)-dependent medium-chain alcohol dehydrogenase from Acinetobacter sp. strain M-1: purification and characterization and gene expression in Escherichia coli

2000

Tani, A.; Sakai, Y.; Ishige, T.; Kato, N.

Appl. Environ. Microbiol.

66

5231-5235

287277

8162187

NADP-dependent alcohol dehydrogenases in bacteria and yeast: purification and partial characterization of the enzymes from Acinetobacter calcoaceticus and Saccharomyces cerevisiae

1994

Wales, M.R.; Fewson, C.A.

Microbiology

140

173-183

287282

4300551

The enzymatic reduction of retinal to retinol in rat intestine

1968

Fidge, N.H.; Goodman, D.S.

J. Biol. Chem.

243

4372-4379

288215

11872467

Wax ester production from n-alkanes by Acinetobacter sp. strain M-1: ultrastructure of cellular inclusions and role of acyl coenzyme A reductase

2002

Ishige, T.; Tani, a.; Takabe, K.; Kawasaki, K.; Sakai, Y.; Kato, N.

Appl. Environ. Microbiol.

68

1192-1195

288472

-

A pyridine nucleotide-independent aldehyde dehydrogenase involved in the alkane oxidation of Acetobacter rancens

1984

Hommel, R.; Kleber, H.P.

FEMS Microbiol. Lett.

22

139-142

348542

1854193

Detection of luciferase gene sequence in nonluminescent Vibrio cholerae by colony hybridization and polymerase chain reaction

1991

Palmer, L.M.; Colwell, R.R.

Appl. Environ. Microbiol.

57

1286-1293

348543

1995589

Cloning and nucleotide sequences of lux genes and characterization of luciferase of Xenorhabdus luminescens from a human wound

1991

Xi, L.; Cho, K.W.; Tu, S.C.

J. Bacteriol.

173

1399-1405

348544

2256783

Relationship of the luminous bacterial symbiont of the Caribbean flashlight fish, Kryptophanaron alfredi (family Anomalopidae) to other luminous bacteria based on bacterial luciferase (luxA) genes

1990

Haygood, M.G.

Arch. Microbiol.

154

496-503

348545

2204626

Nucleotide sequence, expression, and properties of luciferase coded by lux genes from a terrestrial bacterium

1990

Szittner, R.; Meighen, E.

J. Biol. Chem.

265

16581-16587

348546

2376571

A cyanide-aldehyde complex inhibits bacterial luciferase

1990

Makemson, J.C.

J. Bacteriol.

172

4725-4727

348547

2372547

Effects of general anesthetics on the bacterial luciferase enzyme from Vibrio harveyi: an anesthetic target site with differential sensitivity

1990

Curry, S.; Lieb, W.R.; Franks, N.P.

Biochemistry

29

4641-4652

348548

2307667

Elicitation of an oxidase activity in bacterial luciferase by site-directed mutation of a noncatalytic residue

1990

Xi, L.; Cho, K.W.; Herndon, M.E.; Tu, S.C.

J. Biol. Chem.

265

4200-4203

348549

2671993

Bacterial luciferase alpha beta fusion protein is fully active as a monomer and highly sensitive in vivo to elevated temperature

1989

Escher, A.; O'Kane, D.J.; Lee, J.; Szalay, A.A.

Proc. Natl. Acad. Sci. USA

86

6528-6532

348550

-

Localization of luciferase in luminous marine bacteria by gold immunocytochemical labelling

1989

Angell, P.; Langley, D.; Chamberlain, A.H.L.

FEMS Microbiol. Lett.

65

177-182

348551

2680772

Active bacterial luciferase from a fused gene: expression of a Vibrio harveyi luxAB translational fusion in bacteria, yeast and plant cells

1989

Kirchner, G.; Roberts, J.L.; Gustafson, G.D.; Ingolia, T.D.

Gene

81

349-354

348552

2714296

Bioluminescence emission of bacterial luciferase with 1-deaza-FMN. Evidence for the noninvolvement of N(1)-protonated flavin species as emitters

1989

Kurfurst, M.; Macheroux, P.; Ghisla, S.; Hastings, J.W.

Eur. J. Biochem.

181

453-457

348553

-

Expression and localization of bacterial luciferase determined by imunogold labeling

1989

Colepicolo, P.; Nicolas, M.T.; Bassot, J.M.; Hastings, J.W.

Arch. Microbiol.

152

72-76

348554

2653966

A plasmid vector and quantitative techniques for the study of transcription termination in Escherichia coli using bacterial luciferase

1989

Peabody, D.S.; Andrews, C.L.; Escudero, K.W.; Devine, J.H.; Baldwin, T.O.; Bear, D.G.

Gene

75

289-296

348555

3417663

Organization of the lux structural genes of Vibrio harveyi. Expression under the T7 bacteriophage promoter, mRNA analysis, and nucleotide sequence of the luxD gene

1988

Miyamoto, C.M.; Boylan, M.; Graham, A.F.; Meighen, E.A.

J. Biol. Chem.

263

13393-13399

348556

3415691

A new lux gene in bioluminescent bacteria codes for a protein homologous to the bacterial luciferase subunits

1988

Soly, R.R.; Mancini, J.A.; Ferri, S.R.; Boylan, M.; Meighen, E.A.

Biochem. Biophys. Res. Commun.

155

351-358

348557

2491790

Expression of bacterial luciferase genes from Vibrio harveyi in Bacillus subtilis and in Escherichia coli

1989

Karp, M.

Biochim. Biophys. Acta

1007

84-90

348558

2840951

Effects of 3 end deletions from the Vibrio harveyi luxB gene on luciferase subunit folding and enzyme assembly: generation of temperature-sensitive polypeptide folding mutants

1988

Sugihara, J.; Baldwin, T.O.

Biochemistry

27

2872-2880

348559

3311158

Polypeptide folding and dimerization in bacterial luciferase occur by a concerted mechanism in vivo

1987

Waddle, J.J.; Johnston, T.C.; Baldwin, T.O.

Biochemistry

26

4917-4921

348560

3821554

Purification of bacterial luciferase by affinity methods

1986

Baldwin, T.O.; Holzman, T.F.; Holzman, R.B.; Riddle, V.A.

Methods Enzymol.

133

98-108

348561

3821531

Purification of bacterial luciferase by high-performance liquid chromatography

1986

O'Kane, D.J.; Ahmed, M.; Matheson, I.B.C.; Lee, J.

Methods Enzymol.

133

109-128

348562

16593793

Expression and assembly of functional bacteria luciferase in plants

1987

Koncz, C.; Olsson, O.; Langridge, W.H.R.; Schell, J.; Szalay, A.A.

Proc. Natl. Acad. Sci. USA

84

131-135

348563

3026908

Luciferase genes cloned from the unculturable luminous bacteroid symbiont of the Caribbean flashlight fish, Kryptophanaron alfredi

1986

Haygood, MG.; Cohn, D.H.

Gene

45

203-209

348564

-

Identificartions of the true carbon-13 nuclear magnetic resonance spectrum of the stable intermediate II in bacterial luciferase

1986

Vervoort, J.; Muller, F.; Lee, J.; van den Berg, W.A.M.; Moonen, C.T.W.

Biochemistry

25

8062-8067

348565

3514602

Nucleotide sequence of the luxB gene of Vibrio harveyi and the complete amino acid sequence of the beta subunit of bacterial luciferase

1986

Johnston, T.C.; Thompson, R.B.; Baldwin, T.O.

J. Biol. Chem.

261

4805-4811

348566

3997817

Nucleotide sequence of the luxA gene of Vibrio harveyi and the complete amino acid sequence of the alpha subunit of bacterial luciferase

1985

Cohn, D.H.; Milcham, A.J.; Simon, M.I.; Nealson, K.H.; Rausch, S.K.; Bonam, D.; Baldwin, T.O.

J. Biol. Chem.

260

6139-6146

348567

3885942

Expression of the cloned subunits of bacterial luciferase from separate replicons

1985

Gupta, S.C.; O'Brien, D.; Hastings, J.W.

Biochem. Biophys. Res. Commun.

127

1007-1011

348568

3968061

Crystals of luciferase from Vibrio harveyi. A preliminary characterization

1985

Swanson, R.; Weaver, L.H.; Remington, S.J.; Matthews, B.W.; Baldwin, T.O.

J. Biol. Chem.

260

1287-1289

348569

6547953

Affinity labeling of the aldehyde site of bacterial luciferase

1984

Fried, A.; Tu, S.C.

J. Biol. Chem.

259

10754-10759

348570

6089876

Cloning of the luciferase structural genes from Vibrio harveyi and expression of bioluminescence in Escherichia coli

1984

Baldwin, T.O.; Berends, T.; Bunch, T.A.; Holzman, T.F.; Rausch, S.K.; Shamansky, L.; Treat, M.L.; Ziegler, M.M.

Biochemistry

23

3663-3667

348571

-

Reversible Inhibition of the bacterial luciferase catalyzed bioluminescence reaction by aldehyde substrate: Kinetic mechanism and Ligand effects

1983

Holzman, T.F.; Baldwin, T.O.

Biochemistry

22

2838-2846

348572

24234460

Properties of bacterial luciferase/NADH:FMN oxidoreductase and firefly luciferase immobilized onto sepharose

1982

Wienhausen, G.K.; Kricka, L.J.; Hinkley, J.E.; DeLuca, M.

Appl. Biochem. Biotechnol.

7

463-473

348573

6571986

Cloning of the Vibrio harveyi luciferase genes: use of a synthetic oligonucleotide probe

1983

Cohn, D.H.; Ogden, R.C.; Abelson, J.N.; Baldwin, T.O.; Nealson, K.H.; Simon, M.I.; Mileham, A.J.

Proc. Natl. Acad. Sci. USA

80

120-123

348574

7061505

Isolation and properties of bacterial luciferase intermediates containing different oxygenated flavins

1982

Tu, S.C.

J. Biol. Chem.

257

3719-3725

348575

6978813

Structure and catalytic inactivity of the bacterial luciferase neutral flavin radical

1982

Kurfurst, M.; Ghisla, S.; Presswood, R.; Hastings, J.W.

Eur. J. Biochem.

123

355-361

348576

6971121

Active center studies on bacterial luciferase: modification of the enzyme with 2,4-dinitrofluorobenzene

1981

Welches, W.R.; Baldwin, T.O.

Biochemistry

20

512-517

348577

6970544

Inactivation of luciferase from the Luminous marine bacterium Beneckea harveyi by proteases: evidence for a protease labile region and properties of the protein following inactivation

1980

Holzman, T.F.; Riley, P.L.; Baldwin, T.O.

Arch. Biochem. Biophys.

205

554-563

348578

7356469

A proposed mechanism for light emission by bacterial luciferase involving dissociative electron transfer

1980

Kosower, E.M.

Biochem. Biophys. Res. Commun.

92

356-364

348579

309549

Bacterial luciferase: FMNH2-aldehyde oxidase

1978

Hastings, J.W.; Presswood, R.P.

Methods Enzymol.

53

558-570

348580

444472

Interactions of long-chain aldehydes with luciferase. A carbon-13 nuclear magnetic resonance study

1979

Viswanathan, T.S.; Campling, M.R.; Cushley, R.J.

Biochemistry

18

2504-2508

348581

313756

Reversible steps in the reaction of aldehydes with bacterial luciferase intermediates

1979

Baumstark, A.L.; Cline, T.W.; Hastings, J.W.

Arch. Biochem. Biophys.

193

449-455

348582

-

Bacterial luciferase: Assay, purification, and properties

1978

Hastings, J.W.; Baldwin, T.O.; Nicoli, M.Z.

Methods Enzymol.

57

135-152

348583

-

Preparation of the subunits of bacterial luciferase

1978

Tu, S.C.

Methods Enzymol.

57

171-174

348584

-

Preparation of luciferases containing chemically modified subunits

1978

Meighen.E.A.

Methods Enzymol.

57

174-181

348585

363350

Bacterial bioluminescence light emission in the mixed function oxidation of reduced flavin and fatty aldehyde

1978

Hastings, J.W.

CRC Crit. Rev. Biochem.

5

163-184

348586

738995

Studies on luciferase from Photobacterium phosphoreum. XI. Interaction of 8-substituted FMNH2 with luciferase

1978

Watanabe, T.; Matsui, K.; Kasai, S.; Nakamura, T.

J. Biochem.

84

1441-1446

348587

306832

Activity and stability of the luciferase-flavin intermediate

1978

Becvar, J.E.; Tu, S.C.; Hastings, J.W.

Biochemistry

17

1807-1812

348588

305259

Structural studies on bacterial luciferase using energy transfer and emission anisotropy

1978

Tu, S.C.; Wu, C.W.; Hastings, J.W.

Biochemistry

17

987-993

348589

808172

The enthalpy of oxidation of flavin mononucleotide. Temperature dependence of in vitro bacterial luciferase bioluminescence

1975

Mangold, A.; Langerman, N.

Arch. Biochem. Biophys.

169

126-133

348590

4452671

Studies on luciferase from Photobacterium phosphoreum. VII. Interaction with carboxylic acid

1974

Yoshida, K.; Nakamura, T.

J. Biochem.

76

985-990

348591

4426891

Studies on luciferase from Photobacterium phosphoreum. VI. Stoichiometry and mode of binding of FMNH2 and O2 to stripped luciferase

1974

Watanabe, T.; Tomita, G.; Nakamura, T.

J. Biochem.

75

1249-1255

348592

4822498

Bacterial luciferase. Chemistry of the reactive sulfhydryl

1974

Nicoli, M.Z.; Meighen, E.A.; Hastings, J.W.

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