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Ligand p-tolualdehyde

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

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

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.90

4-methylbenzyl alcohol + NAD+ = 4-methylbenzaldehyde + NADH + H+

0

-

Substrate in Enzyme-catalyzed Reactions (28 results)

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Show Substrate (28 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.184

4-methylbenzaldehyde + NADPH + H+ = 4-methylbenzyl alcohol + NADP+

760819

-

1.1.1.2

p-methylbenzaldehyde + NADPH = p-methylbenzyl alcohol + NADP+

286205, 286210

-

1.1.1.2

p-tolualdehyde + NADPH = toluol + NADP+

286164

-

1.1.1.2

2 entries

1.1.1.71

4-methylbenzaldehyde + NADPH + H+ = 4-methylbenzyl alcohol + NADP+

740200

-

1.1.1.91

p-methylbenzaldehyde + NADPH = p-methylbenzyl alcohol + NADP+

389598

-

1.17.3.2

4-methylbenzaldehyde + H2O + O2 = 4-methylbenzoate + H2O2

673434

-

1.2.1.28

4-methylbenzaldehyde + NAD+ + H2O = 4-methylbenzoate + NADH

288328, 390225, 390228

-

1.2.1.28

4-methylbenzaldehyde + NAD+ + H2O = 4-methylbenzoate + NADH + 2 H+

724140

-

1.2.1.28

4-methylbenzaldehyde + NAD+ + H2O = 4-methylbenzoate + NADH + H+

724140

-

1.2.1.3

p-methylbenzaldehyde + NAD+ + H2O = p-methylbenzoate + NADH

348694

-

1.2.1.3

p-tolualdehyde + NAD+ + H2O = p-methylbenzoic acid + NADH

671512

-

1.2.1.28

3 entries

1.2.1.3

2 entries

1.2.1.32

4-methylbenzaldehyde + NAD+ + H2O = 4-methylbenzoate + NADH

389581, 390225, 390259

-

1.2.1.85

4-methylbenzaldehyde + NAD+ + H2O = 4-methylbenzoate + NADH + H+

390225

-

1.2.3.1

4-methylbenzaldehyde + H2O + O2 = 4-methylbenzoate + H2O2

654321

-

1.2.3.1

p-tolualdehyde + H2O + O2 = p-methylbenzoic acid + H2O2

677264

-

1.2.3.1

2 entries

3.4.23.1

4-methylbenzaldehyde + 1-hydroxypropan-2-one = (3R,4S)-3,4-dihydroxy-4-(4-methylphenyl)butan-2-one

755572

-

4.1.1.7

4-Methyl-benzaldehyde + acetaldehyde = 2-Hydroxy-1-p-tolyl-propan-1-one

655499

-

4.1.1.7

4-methylbenzaldehyde + acetaldehyde = (S)-2-Hydroxy-1-p-tolyl-propan-1-one

655230

-

4.1.1.7

4-methylbenzaldehyde = (R)-2-Hydroxy-1,2-di-p-tolyl-ethanone

657382

-

4.1.2.10

cyanide + 4-methyl benzaldehyde = (2R)-(4-methylphenyl)(hydroxy)ethanenitrile

746785

-

4.1.2.10

4-methylbenzaldehyde + nitromethane = 1-(4-methylphenyl)-2-nitroethanol

715698

-

4.1.2.10

cyanide + 4-methylbenzaldehyde = (2R)-(4-methylphenyl)(hydroxy)ethanenitrile

749169, 747326

-

4.1.2.10

cyanide + 4-methylbenzaldehyde = (R)-4-methylmandelonitrile

746692

-

4.1.2.10

HCN + 4-methylbenzaldehyde = (R)-2-hydroxy-2-(4-methylphenyl)acetonitrile

663423

-

4.1.1.7

3 entries

4.1.2.10

5 entries

4.1.2.42

glycine + 4-methylbenzaldehyde = (2R,3S)-2-amino-3-hydroxy-3-(4-methylphenyl)propanoic acid + (2R,3R)-2-amino-3-hydroxy-3-(4-nitrophenyl)propanoic acid

665293

-

4.1.2.45

p-tolualdehyde + pyruvate = (3E)-4-(4-methylphenyl)-2-oxobut-3-enoate + H2O

695728

-

4.1.2.47

cyanide + 4-methylbenzaldehyde = (2S)-(4-methylphenyl)(hydroxy)ethanenitrile

650854

-

4.2.1.84

4-methylbenzaldehyde + HCN + H2O = ? + H2O

654314

-

Product in Enzyme-catalyzed Reactions (10 results)

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Show Product (10 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.2

4-methylbenzyl alcohol + NADP+ = 4-methylbenzaldehyde + NADPH + H+

0

-

1.1.1.90

4-methylbenzyl alcohol + NAD+ = 4-methylbenzaldehyde + NADH + H+

0

-

1.1.3.9

4-methylbenzyl alcohol + O2 = 4-methylbenzaldehyde + H2O2

389850

-

1.2.1.30

4-methylbenzoate + NADPH + H+ + ATP = 4-methylbenzaldehyde + NADP+ + AMP + diphosphate

0

-

1.2.99.6

4-Methylbenzoate + reduced carbamoyl methyl viologen = 4-Methylbenzaldehyde + carbamoyl methyl viologen

0

-

1.4.3.12

4-methylbenzylamine + O2 + H2O = 4-methylbenzaldehyde + NH3 + H2O2

0

-

1.4.3.4

1-(4-methylphenyl)methanamine + H2O + O2 = 4-methylbenzaldehyde + NH3 + H2O2

0

-

4.1.1.7

p-methyl-benzoylformate = p-methyl-benzaldehyde + CO2

0

-

4.1.1.7

(p-methylbenzoyl)formate = p-methylbenzaldehyde + CO2

4799, 0

-

4.1.1.7

2 entries

4.1.1.74

4-methyl-benzoylformic acid = 4-methylbenzaldehyde + CO2

651152

-

Inhibitor in Enzyme-catalyzed Reactions (5 results)

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Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.18.1

-

699195

-

1.2.1.24

-

700082

-

1.2.1.24

1 mM, 64% inhibition

288166

-

1.2.1.24

2 entries

1.2.1.28

substrate inhibition

724140

-

1.2.1.3

substrate inhibition

348694

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (4 results)

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Show Turnover Number (4 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.2.1.28

120

-

apparent Kcat-value, pH 9.6, temperature not specified in the publication

724140

1.2.1.28

120

-

in glycine-KOH buffer (100 mM, pH 9.6), temperature not specified in the publication

724140

1.2.1.28

2 entries

1.2.1.3

3

-

enzyme ALDH-2

348694

4.1.2.10

5520

-

pH 4.2, 22°C

749169

K_M Value (14 results)

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Show KM Value (14 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.2

0.02

-

-

286164

1.1.1.2

0.041

-

-

286205

1.1.1.2

2 entries

1.1.1.91

0.3

-

-

389598

1.17.3.2

0.04

-

pH 7.0

673434

1.2.1.28

0.00097

-

-

288328

1.2.1.28

0.0015

-

-

390225

1.2.1.28

0.003

-

-

288328

1.2.1.28

0.02

-

apparent Km-value, pH 9.6, temperature not specified in the publication

724140

1.2.1.28

0.02

-

in glycine-KOH buffer (100 mM, pH 9.6), temperature not specified in the publication

724140

1.2.1.28

5 entries

1.2.1.3

0.000017

-

enzyme ALDH-2

348694

1.2.1.32

0.53

-

-

390225, 390259

1.2.1.85

0.53

-

in 100 mM glycine-NaOH (pH 9.2), at 25°C

390225

1.2.3.1

1.4

-

pH 7.0, 30°C

677264

4.1.2.10

5.4

-

pH 4.2, 22°C

749169

K_i Value (1 result)

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Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.2.1.28

0.003

-

apparent Ki-value, pH 9.6, temperature not specified in the publication

724140

IC₅₀ Value (3 results)

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Show IC50 Value (3 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.14.18.1

0.12

-

-

699195

1.2.1.24

0.1

-

-

700082

1.2.1.24

1

-

-

700082

1.2.1.24

2 entries

References & Links

Literature References (37)

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Show Reference (37 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

4799

3179267

Differential reactivity in the processing of [p-(halomethyl)benzoyl]formates by benzoylformate decarboxylase, a thiamin pyrophosphate dependent enzyme

1988

Reynolds, L.J.; Garcia, G.A.; Kozarich, J.W.; Kenyon, G.L.

Biochemistry

27

5530-5538

286164

4393513

Purification and characterization of a reduced nicotinamide adenine dinucleotide phosphate-linked aldehyde reductase from brain

1970

Tabakoff, B.; Erwin, G.

J. Biol. Chem.

245

3263-3268

286205

9952458

Purification and characterization of a NADPH-dependent aldehyde reductase from mung bean that detoxifies eutypine, a toxin from Eutypa lata1

1999

Colrat, S.; Latche, A.; Guis, M.; Pech, J.C.; Bouzayen, M.; Fallot, J.; Roustan, J.P.

Plant Physiol.

119

621-626

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

288166

19091

Purification and properties of rat brain succinic semialdehyde dehydrogenase

1977

Cash, C.; Ciesielski, L.; Maitre, M.; Mandel, P.

Biochimie

59

257-268

288328

-

Purification of the benzyl alcohol dehydrogenase and benzaldehyde dehydrogenase encoded by the TOL plasmid pWW53 of Pseudomonas putida MT53 and their preliminary comparison with benzyl alcohol dehydrogenase and benzaldehyde dehydrogenases I and II from Acinetobacter calcoaceticus

1990

Chalmers, R.M.; Scott, A.J.; Fewson, C.A.

J. Gen. Microbiol.

136

637-643

348694

8605195

Kinetics and specificity of human liver aldehyde dehydrogenases toward aliphatic, aromatic, and fused polycyclic aldehydes

1996

Klyosov, A.A.

Biochemistry

35

4457-4467

389581

2202600

Purification and characterisation of TOL plasmid-encoded benzyl alcohol dehydrogenase and benzaldehyde dehydrogenase of Pseudomonas putida

1990

Shaw, J.P.; Harayama, S.

Eur. J. Biochem.

191

705-714

389598

-

Aromatic alcohol dehydrogenase from potato tubers

1973

Davies, D.D.; Ugochukwu, E.N.; Patil, K.D.; Towers, G.H.N.

Phytochemistry

12

531-536

389850

11401560

Catalytic reaction profile for alcohol oxidation by galactose oxidase

2001

Whittaker, M.M.; Whittaker, J.W.

Biochemistry

40

7140-7148

390225

7868591

Overlapping substrate specificities of benzaldehyde dehydrogenase (the xylC gene product) and 2-hydroxymuconic semialdehyde dehydrogenase (the xylG gene product) encoded by TOL plasmid pWW0 of Pseudomonas putida

1995

Inoue, J.; Shaw, J.P.; Rekik, M.; Harayama, S.

J. Bacteriol.

177

1196-1201

390228

2597133

Purification and characterization of benzaldehyde dehydrogenase I from Acinetobacter calcoaceticus [published erratum appears in Biochem J 1990 Feb 1;265(6):931]

1989

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

Biochem. J.

263

913-919

390259

1590768

Substrate-specificity of benzyl alcohol dehydrogenase and benzaldehyde dehydrogenase encoded by TOL plasmid pWW0

1992

Shaw, J.P.; Schwager, F.; Harayama, S.

Biochem. J.

283

789-794

650854

12616635

Substrate specificity of mutants of the hydroxynitrile lyase from Manihot esculenta

2003

Bühler, H.; Effenberger, F.; Förster, S.; Roos, J.; Wajant, H.

ChemBioChem

4

211-216

651152

12752452

Studies on structure-function relationships of indolepyruvate decarboxylase from Enterobacter cloacae, a key enzyme of the indole acetic acid pathway

2003

Schutz, A.; Golbik, R.; Tittmann, K.; Svergun, D.I.; Koch, M.H.; Hubner, G.; Konig, S.

Eur. J. Biochem.

270

2322-2331

654314

14666389

Characterisation of nitrilase and nitrile hydratase biocatalytic systems

2004

Brady, D.; Beeton, A.; Zeevaart, J.; Kgaje, C.; van Rantwijk, F.; Sheldon, R.A.

Appl. Microbiol. Biotechnol.

64

76-85

654321

15657722

Characterization and potential application of purified aldehyde oxidase from Pseudomonas stutzeri IFO12695

2005

Uchida, H.; Fukuda, T.; Satoh, Y.; Okamura, Y.; Toriyama, A.; Yamashita, A.; Aisaka, K.; Sakurai, T.; Nagaosa, Y.; Uwajima, T.

Appl. Microbiol. Biotechnol.

68

53-56

655230

10840971

Benzoylformate decarboxylase from Pseudomonas putida as stable catalyst for the synthesis of chiral 2-hydroxy ketones

2000

Iding, H.; Dünnwald, T.; Greiner, L.; Liese, A.; Müller, M.; et al.

Chem. Eur. J.

6

1483-1495

655499

-

Enantioselective synthesis of (S)-2-hydroxypropanone derivatives by benzoylformate decarboxylase catalyzed C-C bond formation

2000

Dünnwald, T.; Demir, A.S.; Siegert, P.; Pohl, M.; Muller, M.

Eur. J. Org. Chem.

2000

2161-2170

657382

-

Asymmetric benzoin reaction catalyzed by benzoylformate decarboxylase

1999

Demir, A.S.; Dünnwald, T.; Iding, H.; Pohl, M.; Müller, M.

Tetrahedron

10

4769-4774

663423

-

A new (R)-hydroxynitrile lyase from Prunus mume: asymmetric synthesis of cyanohydrins

2005

Nanda, S.; Kato, Y.; Asano, Y.

Tetrahedron

61

10908-10916

665293

-

Enzymic synthesis of beta-hydroxy-alpha-amino acids based on recombinant D- and L-threonine aldolases

1997

Kimura, T.; Vassilev, V.P.; Shen, G.J.; Wong, C.H.

J. Am. Chem. Soc.

119

11734-11742

671512

15812642

Characterization of Sphingomonas aldehyde dehydrogenase catalyzing the conversion of various aromatic aldehydes to their carboxylic acids

2005

Peng, X.; Shindo, K.; Kanoh, K.; Inomata, Y.; Choi, S.K.; Misawa, N.

Appl. Microbiol. Biotechnol.

69

141-150

673434

16715777

Substrate specificity of guinea pig liver aldehyde oxidase and bovine milk xanthine oxidase for methyl- and nitrobenzaldehydes

2005

Veskoukis, A.S.; Kouretas, D.; Panoutsopoulos, G.I.

Eur. J. Drug Metab. Pharmacokinet.

31

11-16

677264

100112090

Purification and some properties of an aldehyde oxidase from Streptomyces rimosus ATCC10970

2006

Uchida, H.; Okamura, Y.; Yamanaka, H.; Fukuda, T.; Haneda, S.; Aisaka, K.; Fujii, Y.

World J. Microbiol. Biotechnol.

22

469-474

695728

10831455

trans-o-Hydroxybenzylidenepyruvate hydratase-aldolase as a biocatalyst

2000

Eaton, R.W.

Appl. Environ. Microbiol.

66

2668-2672

699195

18256890

Quantitative structure-activity relationship studies of mushroom tyrosinase inhibitors

2008

Xue, C.B.; Luo, W.C.; Ding, Q.; Liu, S.Z.; Gao, X.X.

J. Comput. Aided Mol. Des.

22

299-309

700082

18588919

Succinic semialdehyde dehydrogenase from the parasitic cattle tick Rhipicephalus microplus: gene identification, biochemical characterization and comparison with the mouse ortholog

2008

Rothacker, B.; Werr, M.; Ilg, T.

Mol. Biochem. Parasitol.

161

32-43

715698

21439333

Synthesis of (R)-beta-nitro alcohols catalyzed by R-selective hydroxynitrile lyase from Arabidopsis thaliana in the aqueous-organic biphasic system

2011

Fuhshuku, K.; Asano, Y.

J. Biotechnol.

153

153-159

724140

21448720

Purification and characterization of benzyl alcohol- and benzaldehyde-dehydrogenase from Pseudomonas putida CSV86

2011

Shrivastava, R.; Basu, A.; Phale, P.S.

Arch. Microbiol.

193

553-563

740200

23381774

Biochemical characterization of an alcohol dehydrogenase from Ralstonia sp.

2013

Kulig, J.; Frese, A.; Kroutil, W.; Pohl, M.; Rother, D.

Biotechnol. Bioeng.

110

1838-1848

746692

-

Hydroxynitrile lyase isozymes from Prunus communis identification, characterization and synthetic applications

2017

Zheng, Y.; Xu, J.; Wang, H.; Lin, G.; Hong, R.; Yu, H.

Adv. Synth. Catal.

359

1185-1193

746785

26310798

Enantioselective synthesis of various cyanohydrins using covalently immobilized preparations of hydroxynitrile lyase from Prunus dulcis

2015

Alagoez, D.; Tuekel, S.S.; Yildirim, D.

Appl. Biochem. Biotechnol.

177

1348-1363

747326

29975178

Characterization of a novel hydroxynitrile lyase from Nandina domestica Thunb

2018

Isobe, K.; Kitagawa, A.; Kanamori, K.; Kashiwagi, N.; Matsui, D.; Yamaguchi, T.; Fuhshuku, K.I.; Semba, H.; Asano, Y.

Biosci. Biotechnol. Biochem.

82

1760-1769

749169

26261304

Discovery and molecular and biocatalytic properties of hydroxynitrile lyase from an invasive millipede, Chamberlinius hualienensis

2015

Dadashipour, M.; Ishida, Y.; Yamamoto, K.; Asano, Y.

Proc. Natl. Acad. Sci. USA

112

10605-10610

755572

-

Pepsin-catalyzed direct asymmetric aldol reactions for the synthesis of vicinal diol compounds

2015

Li, L.; Yang, D.; Guan, Z.; He, Y.

Tetrahedron

71

1659-1667

760819

-

Understanding (R) specific carbonyl reductase from candida parapsilosis ATCC 7330 [CpCR] Substrate scope, kinetic studies and the role of zinc

2019

Karanam, V.; Chaudhury, D.; Chadha, A.

Catalysts

9

702

Links to other databases for p-tolualdehyde

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Show Links (1 entry)

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