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Ligand 4-hydroxyphenylpyruvate

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Basic Ligand Information

Molecular Structure
Picture of 4-hydroxyphenylpyruvate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H8O4
4-hydroxyphenylpyruvate
KKADPXVIOXHVKN-UHFFFAOYSA-N
Synonyms:
(4-hydroxyphenyl)-pyruvate, (4-hydroxyphenyl)pyruvate, 2-deamino-2-oxotyrosine, 3(4-hydroxyphenyl)-2-oxopropanoate, 3(4-hydroxyphenyl)pyruvate, 3-(4-hydroxyphenyl)-2-oxopropanoate, 3-(4-hydroxyphenyl)-2-oxopropanoic acid, 3-(4-hydroxyphenyl)-2-oxopropionic acid, 3-(4-hydroxyphenyl)pyruvate, 3-p-hydroxyphenylpyruvate, 3-p-hydroxyphenyl pyruvate, 4-(hydroxyphenyl)pyruvate, 4-hydoxyphenylpyruvate, 4-hydroxy-phenylpyruvate, 4-hydroxyhenylpyruvate, 4-hydroxylphenylpyruvate, 4-hydroxyphenylpyruvic acid, 4-hyroxyphenylpyruvate, hydroxyphenylpyruvate, keto-(4-hydroxyphenyl)pyruvate, keto-(p-hydroxyphenyl)pyruvate, p-hydroxy-phenylpyruvate, p-hydroxyphenylpyruvate, p-hydroxyphenylpyruvic acid
Pathway Source
Pathways
BRENDA
(S)-reticuline biosynthesis, tyrosine metabolism
KEGG
2-Oxocarboxylic acid metabolism, Biosynthesis of alkaloids derived from shikimate pathway, Biosynthesis of amino acids, Biosynthesis of cofactors, Biosynthesis of plant secondary metabolites more
MetaCyc
(S)-reticuline biosynthesis I, 3-(4-hydroxyphenyl)pyruvate biosynthesis, 3-hydroxy-L-homotyrosine biosynthesis, 4-hydroxy-3-prenylbenzoate biosynthesis, 4-hydroxybenzoate biosynthesis I (eukaryotes) more


Show all pahtways known for Show all BRENDA pathways known for 4-hydroxyphenylpyruvate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (16 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-(4-hydroxyphenyl)pyruvate + NAD(P)H = (R)-3-(4-hydroxyphenyl)lactate + NAD(P)+
show the reaction diagram
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4-hydroxyphenylpyruvate + NADPH + H+ = 3-(4-hydroxyphenyl)lactate + NADP+
show the reaction diagram
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4-hydroxyphenylpyruvate + O2 = 4-hydroxymandelate + CO2
show the reaction diagram
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4-hydroxyphenylpyruvate + O2 = 4-hydroxyphenylacetate + CO2
show the reaction diagram
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dimethylallyl diphosphate + 4-hydroxyphenylpyruvate = diphosphate + 3-dimethylallyl-4-hydroxyphenylpyruvate
show the reaction diagram
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(2S)-4-hydroxyphenylglycine + 4-hydroxyphenylpyruvate = 4-hydroxybenzoylformate + L-tyrosine
show the reaction diagram
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4-hydroxyphenylpyruvate = 4-hydroxyphenylacetaldehyde + CO2
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (17 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-(4-hydroxyphenyl)lactate + NAD+ = 4-hydroxyphenylpyruvate + NADH + H+
show the reaction diagram
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D-tyrosine + 2-oxoglutarate = 3-(4-hydroxyphenyl)-2-oxopropanoate + D-glutamate
show the reaction diagram
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L-tyrosine + 2-oxoglutarate = 4-hydroxyphenylpyruvate + L-glutamate
show the reaction diagram
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4-hydroxybenzoylformate + L-tyrosine = (2S)-4-hydroxyphenylglycine + 4-hydroxyphenylpyruvate
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (75 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-(4-hydroxyphenyl)pyruvate + NAD(P)H = (R)-3-(4-hydroxyphenyl)lactate + NAD(P)+
show the reaction diagram
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4-hydroxyphenylpyruvate + NADH + H+ = L-4-hydroxyphenyllactate + NAD+
show the reaction diagram
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3-(4-hydroxyphenyl)-2-oxopropanoate + NADH + H+ = 2-hydroxy-3-(4-hydroxyphenyl)propanoate + NAD+
show the reaction diagram
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p-hydroxyphenylpyruvate + NADH + H+ = 2-hydroxy-3-(4-hydroxyphenyl)propanoate
show the reaction diagram
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4-hydroxyphenylpyruvate + NADPH + H+ = 3-(4-hydroxyphenyl)lactate + NADP+
show the reaction diagram
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4-hydroxyphenylpyruvate + NADH + H+ = 4-hydroxyphenyllactate + NAD+
show the reaction diagram
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4-hydroxyphenylpyruvate + O2 = phenylpyruvate + H2O2
show the reaction diagram
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4-hydroxyphenylpyruvate + O2 = 4-hydroxymandelate + CO2
show the reaction diagram
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4-hydroxyphenylpyruvate + O2 = 4-hydroxyphenylacetate + CO2
show the reaction diagram
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4-hydroxyphenylpyruvate + CoA + 2 methyl viologen = (4-hydroxyphenyl)acetyl-CoA + CO2 + 2 reduced methyl viologen + 2 H+
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hydroxyphenylpyruvate + CoA + oxidized ferredoxin = 4-hydroxyphenylacetyl-CoA + CO2 + reduced ferredoxin
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p-hydroxyphenylpyruvate + NADPH + NH3 = L-tyrosine + NADP+ + H2O
show the reaction diagram
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dimethylallyl diphosphate + 4-hydroxyphenylpyruvate = diphosphate + 3-dimethylallyl-4-hydroxyphenylpyruvate
show the reaction diagram
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L-aspartate + 4-hydroxyphenylpyruvate = oxaloacetate + L-tyrosine
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L-leucine + p-hydroxyphenylpyruvate = 2-oxoisohexanoate + L-tyrosine
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4-hydroxyphenylpyruvate + L-aspartate = L-tyrosine + oxaloacetate
show the reaction diagram
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4-hydroxyphenylpyruvate + L-glutamate = L-tyrosine + 2-oxoglutarate
show the reaction diagram
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(2S)-4-hydroxyphenylglycine + 4-hydroxyphenylpyruvate = 4-hydroxybenzoylformate + L-tyrosine
show the reaction diagram
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4-hydroxyphenylpyruvate = ?
show the reaction diagram
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4-hydroxyphenylpyruvate = 4-hydroxyphenylacetaldehyde + CO2
show the reaction diagram
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4-hydroxyphenylpyruvate = (4-hydroxyphenyl)acetaldehyde + CO2
show the reaction diagram
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4-hydroxyphenylpyruvate = 4-hydroxyphenylacetaldehyde + CO2
show the reaction diagram
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4-hydroxyphenylpyruvate = 4-hydroxyphenylpyruvate
show the reaction diagram
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3-(4-hydroxyphenyl)pyruvate + glyoxylate = ?
show the reaction diagram
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4-hydoxyphenylpyruvate = ?
show the reaction diagram

Product in Enzyme-catalyzed Reactions (104 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
p-hydroxyphenyllactate + NAD+ = p-hydroxyphenylpyruvate + NADH
show the reaction diagram
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3-(4-hydroxyphenyl)lactate + NAD+ = 4-hydroxyphenylpyruvate + NADH + H+
show the reaction diagram
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DL-p-hydroxy-beta-phenyllactate + 2,6-dichlorophenolindophenol = (4-hydroxyphenyl)pyruvate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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2-hydroxy-2-(4-hydroxyphenyl)acetate + O2 = (4-hydroxyphenyl)pyruvate + H2O2
show the reaction diagram
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L-tyrosine + O2 = 3-(4-hydroxyphenyl)-2-oxopropanoic acid + NH3
show the reaction diagram
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prephenate + NADP+ = 3-(4-hydroxyphenyl)-2-oxopropanoate + CO2 + NADPH
show the reaction diagram
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L-tyrosine + H2O + NAD+ = (4-hydroxyphenyl)pyruvate + NH3 + NADH
show the reaction diagram
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L-Tyr + O2 + H2O = 3-(4-hydroxyphenyl)-2-oxopropionic acid + NH3 + H2O2
show the reaction diagram
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L-tyrosine + H2O + 2 cytochrome b = 4-hydroxyphenylpyruvate + NH3 + 2 reduced cytochrome b
show the reaction diagram
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2-oxosuccinamic acid + L-tyrosine = L-asparagine + 3-(4-hydroxyphenyl)-2-oxopropanoate
show the reaction diagram
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D-tyrosine + 2-oxoglutarate = 3-(4-hydroxyphenyl)-2-oxopropanoate + D-glutamate
show the reaction diagram
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L-tyrosine + 2-oxoglutarate = (4-hydroxyphenyl)pyruvate + L-glutamate
show the reaction diagram
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L-phenylalanine + 2-oxoglutarate = 3-(4-hydroxyphenyl)-2-oxopropanoate + L-glutamate
show the reaction diagram
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phenylpyruvate + L-tyrosine = phenylalanine + 3-(4-hydroxyphenyl)-2-oxopropanoate
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2-oxoglutarate + L-tyrosine = L-glutamate + 4-hydroxyphenylpyruvate
show the reaction diagram
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L-tyrosine + 2-oxoglutarate = 3-(4-hydroxyphenyl)-2-oxopropanoate + L-glutamate
show the reaction diagram
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L-tyrosine + pyruvate = 3-(4-hydroxyphenyl)-2-oxopropanoate + L-alanine
show the reaction diagram
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tyrosine + glyoxylate = 3-(4-hydroxyphenyl)-2-oxopropanoate + glycine
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tyrosine + glyoxylate = 3-(4-hydroxyphenyl)-2-oxopropanoate + glycine
show the reaction diagram
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2-oxo-4-methylthiobutanoate + L-tyrosine = L-methionine + 4-hydroxyhenylpyruvate
show the reaction diagram
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L-tyrosine + indole-3-pyruvic acid = 3-(4-hydroxyphenyl)-2-oxopropanoate + L-tryptophan
show the reaction diagram
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4-hydroxyphenylpyruvate = 4-hydroxyphenylpyruvate
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (25 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
substrate inhibition
-
1 mM, 68% inhibition, substrate analogue
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above 0.4 mM iron, activation below
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potent inhibitor when hydroxypyruvate is used as a substrate, whereas noncompetitive inhibition with fructose-6-phosphate
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substrate inhibition
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5 mM
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substrate inhibition
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competitive
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heat-purified enzyme, at low concentrations, pH 7-8
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3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (100 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
788
-
pH 7.0, temperature not specified in the publication
0.122
-
pH 7.0, 30°C, recombinant enzyme
0.833
-
pH 6.9, 85°C, under argon
90
-
25°C, pH 10.4
620
-
pH 8.0, 25°C
11
-
wild type enzyme, in 100 mM KPO4 buffer (pH 7.0), 1 mM MgSO4, 0.5 mM thiamine diphosphate, at pH 7.0 and 30°C
3.89
-
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1.65
-
at pH 6.5, temperature not specified in the publication

KM Value (133 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.6
-
pH 7.0, temperature not specified in the publication
2.7
-
-
0.8
-
pH 7.0, 30°C, recombinant enzyme
1.9
-
-
0.14
-
pH 8.0, 25°C
0.09
-
wild type enzyme, in 100 mM KPO4 buffer (pH 7.0), 1 mM MgSO4, 0.5 mM thiamine diphosphate, at pH 7.0 and 30°C
0.63
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in 50 mM potassium phosphate buffer, pH 6.8 in the presence of 2.5 mM MgSO4 and 0.1 mM thiamine diphosphate
5.86
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at pH 6.5, temperature not specified in the publication
0.67
-
-
7.7
-
-

Ki Value (12 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.23
-
-
0.0037
-
-
0.305
-
with hydroxypyruvate as substrate
22.11
-
at pH 6.5, temperature not specified in the publication

References & Links

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Links to other databases for 4-hydroxyphenylpyruvate

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ChEBI
PubChem
ChEBI
PubChem