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Ligand phenylpyruvate

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Basic Ligand Information

Molecular Structure
Picture of phenylpyruvate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H8O3
phenylpyruvate
BTNMPGBKDVTSJY-UHFFFAOYSA-N
Synonyms:
2-oxo-3-phenylpropanoate, 2-oxo-3-phenylpropanoic acid, 2-oxo-3-phenylpropionic acid, 3-phenyl-2-oxopropanoate, 3-phenylpyruvate, 3-phenylpyruvic acid, beta-phenylpyruvate, DL-phenylpyruvate, keto-phenylpyruvate, L-phenylpyruvate, phenylpyruvic acid, phenylpyuravte
Pathway Source
Pathways
BRENDA
bacilysin biosynthesis, methionine metabolism, phenylalanine metabolism, tryptophan metabolism
KEGG
2-Oxocarboxylic acid metabolism, Biosynthesis of amino acids, Biosynthesis of plant secondary metabolites, Biosynthesis of secondary metabolites, D-Amino acid metabolism more
MetaCyc
(-)-microperfuranone biosynthesis, 5-(methoxycarbonylmethoxy)uridine biosynthesis, bacilysin biosynthesis, L-homophenylalanine biosynthesis, L-methionine degradation III more


Show all pahtways known for Show all BRENDA pathways known for phenylpyruvate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (15 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenylpyruvate + NADH = phenyllactate + NAD+
show the reaction diagram
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phenylpyruvate + NADH = phenyllactate + NAD+
show the reaction diagram
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phenylpyruvate + NADH + H+ = (R)-3-phenyllactate + NAD+
show the reaction diagram
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phenylpyruvate + NH3 + NADH = L-phenylalanine + H2O + NAD+
show the reaction diagram
L-tryptophan + phenylpyruvate = 3-indole-2-oxopropanoate + L-phenylalanine
show the reaction diagram
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L-glutamine + phenylpyruvate = 2-oxoglutaramate + L-phenylalanine
show the reaction diagram
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L-aspartate + 3-phenylpyruvate = oxaloacetate + L-phenylalanine
show the reaction diagram
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Phenylpyruvate = Phenylacetaldehyde + CO2
show the reaction diagram

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
D-phenylalanine + 2-oxoglutarate = phenylpyruvate + D-glutamate
show the reaction diagram
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L-phenylalanine + pyruvate = phenylpyruvate + L-alanine
show the reaction diagram
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prephenate = phenylpyruvate + H2O + CO2
show the reaction diagram
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phenylenolpyruvate = phenylpyruvate
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (196 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenylpyruvate + NAD(P)H = D-phenyllactate + NAD(P)+
show the reaction diagram
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phenylpyruvate + NADH = phenyllactate + NAD+
show the reaction diagram
-
phenylpyruvate + NADH + H+ = 3-phenyllactate + NAD+
show the reaction diagram
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phenylpyruvate + NADH + H+ = ? + NAD+
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phenylpyruvate + NADH + H+ = ?
show the reaction diagram
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phenylpyruvate + NAD(P)H = phenyllactate + NAD(P)+
show the reaction diagram
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phenylpyruvate + NADH = phenyllactate + NAD+
show the reaction diagram
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phenylpyruvate + reduced acceptor = phenyl-(R)-lactate + acceptor
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phenylpyruvate + O2 = 2-hydroxyphenylacetate + CO2
show the reaction diagram
phenylpyruvic acid + O2 = ?
show the reaction diagram
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phenylpyruvate + NADPH + H+ + O2 = phenylacetate + NADP+ + H2O + CO2
show the reaction diagram
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phenylpyruvate + O2 = phenylacetate + CO2
show the reaction diagram
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phenylpyruvate + CoA + 2 methyl viologen = phenylacetyl-CoA + CO2 + 2 reduced methyl viologen + 2 H+
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phenylpyruvate + CoA + oxidized ferredoxin = phenylacetyl-CoA + CO2 + reduced ferredoxin
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phenylpyruvate + NH3 + NADH = L-phenylalanine + H2O + NAD+
show the reaction diagram
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beta-phenylpyruvate + NADPH + NH3 = L-phenylalanine + NADP+ + H2O
show the reaction diagram
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phenylpyruvate + NH3 + NADH = L-Phe + H2O + NAD+
show the reaction diagram
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phenylpyruvate + methylamine + NADPH = N-methylphenylalanine + NADP+ + H2O
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phenylpyruvate + methylamine + NADPH + H+ = N-methyl-L-phenylalanine + NADP+
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phenylpyruvate + 2-aminoadipate = L-phenylalanine + 2-oxoglutarate
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L-alanine + phenylpyruvate = pyruvate + L-phenylalanine
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3-(3,4-dihydroxyphenyl)-L-alanine + 3-phenylpyruvate = 3-(3,4-dihydroxyphenyl)pyruvate + L-phenylalanine
show the reaction diagram
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phenylpyruvate + L-aspartate = L-phenylalanine + oxaloacetate
show the reaction diagram
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phenylpyruvate + L-glutamate = L-phenylalanine + 2-oxoglutarate
show the reaction diagram
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2-Oxo-3-phenylpropionic acid = Acetophenone + CO2
show the reaction diagram
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phenylpyruvate = phenylethanal + CO2
show the reaction diagram
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Phenylpyruvate = Phenylpyruvate
show the reaction diagram
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phenylpyruvic acid = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (157 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenyllactate + NAD+ = phenylpyruvate + NADH
show the reaction diagram
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(2S)-hydroxy-3-phenylpropanoic acid + acceptor = 2-oxo-3-phenylpropanoic acid + reduced acceptor
show the reaction diagram
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L-phenylalanine + H2O + O2 = 2-oxo-3-phenylpropanoic acid + NH3
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L-Phe + O2 = beta-phenylpyruvate + NH3 + H2O2
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L-phenylalanine + NAD+ + H2O = phenylpyruvate + NH3 + NADH + H+
show the reaction diagram
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L-phenylalanine + H2O + NAD+ = phenylpyruvate + NH3 + NADH
show the reaction diagram
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L-phenylalanine + H2O + NAD+ = 2-oxo-3-phenylpropanoic acid + NH3 + NADH
show the reaction diagram
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L-Phe + H2O + NAD+ = phenylpyruvate + NH3 + NADH
show the reaction diagram
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L-phenylalanine + O2 + H2O = phenylpyruvate + NH3 + H2O2
show the reaction diagram
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D-phenylalanine + H2O + O2 = phenylpyruvate + NH3 + H2O2
show the reaction diagram
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D-phenylalanine + oxidized 2,6-dichloroindophenol + H2O = phenylpyruvate + NH3 + reduced 2,6-dichloroindophenol
show the reaction diagram
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pyruvate + L-phenylalanine = L-alanine + 2-oxo-3-phenylpropanoate
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L-phenylalanine + 2-oxoglutarate = phenylpyruvate + L-glutamate
show the reaction diagram
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L-tyrosine + 2-oxoglutarate = 2-oxo-3-phenylpropanoate + L-glutamate
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L-phenylalanine + 2-oxoglutarate = phenylpyruvate + L-glutamate
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L-phenylalanine + 4,5-dioxopentanoate = phenylpyruvate + 5-aminolevulinate
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3-(3,4-dihydroxyphenyl)pyruvate + L-phenylalanine = 3,4-dihydroxy-L-phenylalanine + 3-phenylpyruvate
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L-phenylalanine + pyruvate = phenylpyruvate + L-alanine
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phenylalanine + glyoxylate = phenylpyruvate + glycine
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2-oxo-4-methylthiobutanoate + L-phenylalanine = L-methionine + 2-oxo-3-phenylpropanoate
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L-phenylalanine + 2-oxoglutarate = phenylpyruvate + L-glutamate
show the reaction diagram
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L-phenylalanine + indole-3-pyruvic acid = phenylpyruvate + L-tryptophan
show the reaction diagram
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L-phenylalanine + 2-oxoglutarate = phenylpyruvate + L-glutamate
show the reaction diagram
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L-phenylalanine + H2O = 2-oxo-3-phenylpropanoate + NH3
show the reaction diagram
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Phenylpyruvate = Phenylpyruvate
show the reaction diagram
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L-phenylalanine + pyridoxal 5'-phosphate = 2-oxo-3-phenylpropanoate + pyridoxamine 5'-phosphate
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Activator in Enzyme-catalyzed Reactions (1 result)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activates
-

Inhibitor in Enzyme-catalyzed Reactions (34 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
low-molecular weight aldehyde reductase, noncompetitively inhibition
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substrate inhibition
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competitive inhibition
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partial inhibition
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100% inhibition at 0.08 mM
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DAHP synthase-tyr
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shows substrate inhibition at 4 mM
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substrate inhibition
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the enzyme decreases the activity of enzyme in the presence and absence of glucose-6-phosphate (G6P) and increases the release of the enzyme from mitochondria
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competitive with ADP and phosphoenolpyruvate, Ala prevents inhibition
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1 mM
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10 mM, 81% inhibition
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competitive against indole-3-acetic acid
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enzyme form OAT-2 is inhibited, enzyme form OAT-1 not
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3D Structure of Enzyme-Ligand-Complex (PDB) (30 results)

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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (112 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.37
-
pH 7.0, 37°C
0.88
-
pH 7.5, 25°C
0.8
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pH 8.0, 30°C
9.1
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pH 7.0, 48°C
52
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half transamination reaction, pH 8.0, 90°C
130
-
pH 8.0, 25°C
2
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mutant enzyme T377L/A460Y, at pH 6.0 and 30°C

KM Value (157 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.106
-
-
0.8
-
pH 7.0, 37°C
0.353
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pH 7.5, 25°C
0.043
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in the presence of NADPH, in 50 mM sodium phosphate, pH 8.0, 500 mM NaCl, and 30% (v/v) glycerol, at 25°C
0.22
-
pH 6.9, 85°C, under argon
2.5
-
pH 8.0, 30°C
0.45
-
cosubstrate L-asparagine
1.43
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pH 7.0, 48°C
0.82
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mutant enzyme T377L/A460Y, at pH 6.0 and 30°C
1.66
-
70°C, pH 8.0

Ki Value (10 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
23
-
pH 7.0, 30°C, recombinant enzyme

IC50 Value (2 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.135
-
pH and temperature not specified in the publication
0.346
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at pH 7.5 and 25°C

References & Links

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Links to other databases for phenylpyruvate

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ChEBI
PubChem
ChEBI
PubChem