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Ligand terephthalic acid

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

1.14.12.15

terephthalate + NADH + O2 + H+ = (1R,2S)-dihydroxy-3,5-cyclohexadiene-1,4-dicarboxylate + NAD+

658766

7q05, 3D-view

Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Substrate (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.12.15

terephthalate + NAD(P)H + O2 + H+ = (1R,2S)-dihydroxy-3,5-cyclohexadiene-1,4-dicarboxylate + NAD(P)+

671450, 702731

7q05, 3D-view

1.14.12.15

terephthalate + NADH + O2 + H+ = (1R,2S)-dihydroxy-3,5-cyclohexadiene-1,4-dicarboxylate + NAD+

7067, 673720, 702731, 658766

7q05, 3D-view

1.14.12.15

2 entries

3.1.1.3

terephthalate + ethanol = terephthalic acid monoethyl ester + terephthalic acid diethyl ester + H2O

693692

-

Product in Enzyme-catalyzed Reactions (24 results)

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Show Product (24 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.145

4-carboxybenzaldehyde + NADP+ + H2O = 4-carboxybenzoic acid + NADPH + H+

0

-

1.2.1.24

4-carboxybenzaldehyde + NAD(P)+ + H2O = 4-carboxybenzoate + NAD(P)H + H+

0

-

1.2.1.24

4-carboxybenzaldehyde + NAD+ + H2O = 4-carboxybenzoate + NADH + H+

0

-

1.2.1.24

2 entries

1.2.1.28

4-carboxybenzaldehyde + NAD+ + H2O = 4-carboxybenzoate + NADH

390225

-

1.2.1.3

4-carboxybenzaldehyde + NAD+ + H2O = 4-carboxybenzoate + NADH

0

-

1.2.1.3

p-carboxybenzaldehyde + NAD+ + H2O = p-carboxybenzoate + NADH

0

-

1.2.1.3

2 entries

1.2.1.32

4-carboxybenzaldehyde + NAD+ + H2O = 4-carboxybenzoate + NADH

0

-

1.2.1.5

4-carboxybenzaldehyde + NADP+ + H2O = 4-carboxybenzoate + NADPH + H+

0

-

1.2.1.65

4-carboxybenzaldehyde + NAD+ + H2O = 4-carboxybenzoate + NADH + 2 H+

0

-

1.2.1.79

4-carboxybenzaldehyde + NADP+ + H2O = 4-carboxybenzoate + NADPH + H+

0

-

1.2.3.1

terephthalaldehyde + H2O + O2 = terephthalic acid + H2O2

0

-

1.2.3.9

terephthalaldehyde + O2 + H2O = terephthalic acid + H2O2

0

-

1.2.99.6

terephthalaldehyde + carbamoyl methyl viologen = terephthalate + reduced carbamoyl methyl viologen

11939

-

3.1.1.101

(ethylene terephthalate)n + H2O = terephthalic acid + mono(2-hydroxyethyl)terephthalate + ?

0

-

3.1.1.102

ethylene terephthalate + H2O = terephthalate + ethylene glycol

0

-

3.1.1.102

bis(2-hydroxyethyl) terephthalic acid + 2 H2O = terephthalic acid + 2 ethylene glycol

0

-

3.1.1.102

2 entries

3.1.1.2

[(3-[(3-hydroxypropoxy)carbonyl]-5-[[3-([4-[(3-hydroxypropoxy)carbonyl]benzoyl]oxy)propoxy]carbonyl]phenyl)-lambda4-sulfanetriyl]tris(oxidanide) + H2O = terephthalic acid + 5-sulfoisophthalic acid + 1,3-propanediol

0

-

3.1.1.74

bis(benzoyloxyethyl) terephthalate + H2O = terephthalate + benzoic acid + 2-hydroxyethylbenzoate + mono-(2-hydroxyethyl) terephthalate + bis-(2-hydroxyethyl) terephthalate

0

-

3.1.1.74

poly(ethylene terephthalate) + H2O = terephthalate + ?

0

-

3.1.1.74

polyethylene terephthalate + H2O = terephthalate + ?

0

-

3.1.1.74

polyethyleneterephthalate + H2O = terephthalate + benzoic acid + 2-hydroxyethylbenzoate + mono-(2-hydroxyethyl)terephthalate + bis-(2-hydroxyethyl)terephthalate

0

-

3.1.1.74

(ethylene terephthalate)n + H2O = terephthalic acid + mono(2-hydroxyethyl)terephthalate + ?

0

-

3.1.1.74

bisbenzoyloxyethyl terephthalate + H2O = terephthalic acid + mono(2-hydroxyethyl) terephthalate + bis(2-hydroxyethyl)terephthalate + benzoic acid + 2-hydroxyethyl benzoate

0

-

3.1.1.74

poly(ethylene terephthalate) + H2O = mono-(2-hydroxyethyl) terephthalate + terephthalic acid

0

-

3.1.1.74

7 entries

Inhibitor in Enzyme-catalyzed Reactions (6 results)

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Show Inhibitors (6 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.11.2

competitive inhibition with respect to ascorbate

439194

-

1.14.11.2

competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+

439193

-

1.14.11.2

2 entries

1.14.11.7

-

349014

-

1.2.1.105

-

349014

-

4.1.1.55

competitive

4714

-

4.3.1.10

50 mM, 53% inhibition

6032

-

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

1.14.12.15

7q05, 3D-view

3.2.1.17

7q05, 3D-view

Enzyme Kinetic Parameters

K_M Value (2 results)

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Show KM Value (2 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.12.15

0.072

-

at 30°C

702731

1.2.99.6

4

-

with reduced carbamoyl methyl viologen as cosubstrate

11939

K_i Value (3 results)

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Show KI Value (3 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.11.2

3.3

-

-

439193

1.14.11.7

0.5

-

competitive inhibition with respect to 2-oxoglutarate and noncompetitive with respect to Fe2+ and the peptide substrate

349014

1.2.1.105

1.1

-

-

349014

References & Links

Literature References (13)

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Show Reference (13 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

4714

29563

Phthalate and 4-hydroxyphthalate metabolism in Pseudomonas testosteroni: purification and properties of 4,5-dihydroxyphthalate decarboxylase

1978

Nakazawa, T.; Hayashi, E.

Appl. Environ. Microbiol.

36

264-269

6032

4772681

Studies on the inhibition of the L-serine O-sulphate-degrading system of pig liver and the topography of its active site

1973

Tudball, N.; Thomas, P.

Eur. J. Biochem.

40

25-29

7067

7961417

Terephthalate 1,2-dioxygenase system from Comamonas testosteroni T-2: purification and some properties of the oxygenase component

1994

Schlaefli, H.R.; Weiss, M.A.; Leisinger, T.; Cook, A.M.

J. Bacteriol.

176

6644-6652

11939

-

Pterin cofactor, substrate specificity, and observations on the kinetics of the reversible tungsten-containing aldehyde oxidoreductase from Clostridium thermoaceticum

1995

Huber, C.; Skopan, H.; Feicht, R.; White, H.; Simon, H.

Arch. Microbiol.

164

110-118

349014

2994628

Differences between collagen hydroxylases and 2-oxoglutarate dehydrogenase in their inhibition by structural analogues of 2-oxoglutarate

1985

Majamaa, K.; Turpeenniemi-Hujanen, T.M.; Latipää, P.; Gunzler, V.; Hanauske-Abel, H.M.; Hassinen, I.E.; Kivirikko, K.I.

Biochem. J.

229

127-133

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

439193

6321169

The 2-oxoglutarate binding site of prolyl 4-hydroxylase. Identification of distinct subsites and evidence for 2-oxoglutarate decarboxylation in a ligand reaction at the enzyme-bound ferrous ion

1984

Majamaa, K.; Hanauske-Abel, H.M.; Gunzler, V.; Kivirikko, K.I.

Eur. J. Biochem.

138

239-245

439194

3011801

Partial identity of the 2-oxoglutarate and ascorbate binding sites of prolyl 4-hydroxylase

1986

Majamaa, K.; Gunzler, V.; Hanauske-Abel, H.M.; Myllylä, R.; Kivirikko, K.I.

J. Biol. Chem.

261

7819-7823

658766

12670689

Purification and gene cloning of the oxygenase component of the terephthalate 1,2-dioxygenase system from Delftia tsuruhatensis strain T7

2003

Shigematsu, T.; Yumihara, K.; Ueda, Y.; Morimura, S.; Kida, K.

FEMS Microbiol. Lett.

220

255-260

671450

16517628

Characterization of the terephthalate degradation genes of Comamonas sp. strain E6

2006

Sasoh, M.; Masai, E.; Ishibashi, S.; Hara, H.; Kamimura, N.; Miyauchi, K.; Fukuda, M.

Appl. Environ. Microbiol.

72

1825-1832

673720

16181748

Molecular and biochemical analysis of phthalate and terephthalate degradation by Rhodococcus sp. strain DK17

2005

Choi, K.Y.; Kim, D.; Sul, W.J.; Chae, J.; Zylstra, G.J.; Kim, Y.M.; Kim, E.

FEMS Microbiol. Lett.

252

207-213

693692

-

Selective esterification of phthalic acids in two ionic liquids at high temperatures using a thermostable lipase of Bacillus thermocatenulatus: A comparative study

2008

Martin, J.R.; Nus, M.; Gago, J.V.; Sanchez-Montero, J.M.

J. Mol. Catal. B

52-53

162-167

702731

18776687

Enzymatic properties of terephthalate 1,2-dioxygenase of Comamonas sp. strain E6

2008

Fukuhara, Y.; Kasai, D.; Katayama, Y.; Fukuda, M.; Masai, E.

Biosci. Biotechnol. Biochem.

72

2335-2341

Links to other databases for terephthalic acid

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Show Links (1 entry)

ChEBI

PubChem