Ligand L-phenylalanine

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Basic Ligand Information

Molecular Structure
Picture of L-phenylalanine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H11NO2
L-phenylalanine
COLNVLDHVKWLRT-QMMMGPOBSA-N
Synonyms:
(2S)-2-amino-3-phenylpropanoic acid, L-alpha-phenylalanine, L-Phe, L-phenylalanine[side 2], L-phenylanine, Phe, Phe-OH, phenylalanine
Pathway Source
Pathways


Show all pahtways known for Show all BRENDA pathways known for L-phenylalanine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (41 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-phenylalanine + O2 = ? + H2O2
show the reaction diagram
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L-phenylalanine + tetrahydrobiopterin + O2 = 3-hydroxy-L-phenylalanine + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
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acetyl-CoA + L-phenylalanine = CoA + N-acetyl-L-phenylalanine
show the reaction diagram
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L-phenylalanine + pyruvate = phenylpyruvate + L-alanine
show the reaction diagram
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L-phenylalanine + O2 + H2O = phenylacetaldehyde + CO2 + NH3 + H2O2
show the reaction diagram
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L-phenylalanine = (E)-cinnamate + NH3
show the reaction diagram
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L-phenylalanine = L-beta-phenylalanine
show the reaction diagram
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L-phenylalanine = D-beta-phenylalanine
show the reaction diagram
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ATP + H2O + phenylalanine/out = ADP + phosphate + phenylalanine/in
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (18 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenylpyruvate + NH3 + NADH = L-phenylalanine + H2O + NAD+
show the reaction diagram
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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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L-Phe benzyl ester + H2O = benzyl alcohol + L-phenylalanine
show the reaction diagram
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Leu-Phe + H2O = Leu + Phe
show the reaction diagram
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methotrexate-phenylalanine + H2O = methotrexate + phenylalanine
show the reaction diagram
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FVNQHLCGSHLVEALYLVCGERGFFYTPKA + 6 H2O = FVNQHL + CGSHL + VEAL + L-Tyr + LVCGERGF + L-Phe + YTPKA
show the reaction diagram
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N-acetyl-L-phenylalanine + H2O = acetate + L-phenylalanine
show the reaction diagram
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trans-cinnamate + NH3 = L-phenylalanine
show the reaction diagram
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D-Phe = L-Phe
show the reaction diagram
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ATP + H2O + phenylalanine/out = ADP + phosphate + phenylalanine/in
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (266 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-phenylalanine + O2 = ? + H2O2
show the reaction diagram
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L-phenylalanine + O2 = 2-oxo-3-phenylpropanoic acid + NH3
show the reaction diagram
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L-phenylalanine + O2 = phenylacetamide + CO2 + H2O
show the reaction diagram
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phenylalanine + NAD(P)H + O2 = tyrosine + NAD(P)+ + H2O
show the reaction diagram
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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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L-Phe + pyruvate + NADH = N-[1-(R)-(Carboxy)ethyl]-(S)-Phe + NAD+
show the reaction diagram
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acetyl-CoA + L-phenylalanine = CoA + N-acetyl-L-phenylalanine
show the reaction diagram
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acetyl-CoA + L-phenylalanine = CoA + N-acetyl-L-phenylalanine
show the reaction diagram
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pyruvate + L-phenylalanine = L-alanine + 2-oxo-3-phenylpropanoate
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 + 2-oxoglutarate = 3-(4-hydroxyphenyl)-2-oxopropanoate + L-glutamate
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 + 4,5-dioxopentanoate = phenylpyruvate + 5-aminolevulinate
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3-(3,4-dihydroxyphenyl)pyruvate + L-phenylalanine = 3,4-dihydroxy-L-phenylalanine + 3-phenylpyruvate
show the reaction diagram
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L-phenylalanine + pyruvate = phenylpyruvate + L-alanine
show the reaction diagram
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phenylalanine + glyoxylate = phenylpyruvate + glycine
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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
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Phe + Leu = Gly + Gly + Gly
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L-phenylalanine ethyl ester + L-phenylalanine + H2O = L-Phe-L-Phe + cyclo(L-phenylalanine-L-phenylalanine) + L-Phe-L-Phe ethyl ester
show the reaction diagram
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lactate + L-phenylalanine = N-L-lactoyl-L-phenylalanine + H2O
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L-phenylalanine + H2O = 2-oxo-3-phenylpropanoate + NH3
show the reaction diagram
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L-phenylalanine + O2 + H2O = phenylacetaldehyde + CO2 + NH3 + H2O2
show the reaction diagram
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L-phenylalanine + O2 + H2O = phenylacetaldehyde + CO2 + NH3 + H2O2
show the reaction diagram
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L-Phe = 2-phenylethylamine + CO2
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L-Phe = phenylethylamine + CO2
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L-phenylalanine = phenylacetic acid + CO2
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L-phenylalanine = phenylethylamine + CO2
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L-phenylalanine = cinnamic acid + NH3
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L-phenylalanine = (E)-cinnamate + NH3
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L-phenylalanine = (E)-cinnamate + NH3
show the reaction diagram
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L-Phe = (E)-cinnamate + NH3
show the reaction diagram
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L-phenylalanine + pyridoxal 5'-phosphate = 2-oxo-3-phenylpropanoate + pyridoxamine 5'-phosphate
show the reaction diagram
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L-phenylalanine = D-phenylalanine
show the reaction diagram
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L-phenylalanine = D-phenylalanine
show the reaction diagram
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L-phenylalanine = L-beta-phenylalanine
show the reaction diagram
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L-phenylalanine = L-beta-phenylalanine
show the reaction diagram
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ATP + L-phenylalanine + tRNAPyl = AMP + diphosphate + L-phenylalanyl-tRNAPyl
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ATP + L-arginine + phenylalanine = ? + AMP
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ATP + detyrosinated alpha-tubulin + L-Phe = ?
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ATP + (-)-jasmonate + L-Phe = AMP + diphosphate + jasmonoyl-L-Phe
show the reaction diagram
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ATP + H2O + L-phenylalanine/out = ADP + phosphate + L-phenylalanine/in
show the reaction diagram
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ATP + H2O + phenylalanine/out = ADP + phosphate + phenylalanine/in
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (456 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-phenylalanine + 6-methyltetrahydropterin + O2 = L-phenylalanine + 6-methyldihydropterin + H2O2
show the reaction diagram
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phenylpyruvate + NH3 + NADH = L-phenylalanine + H2O + NAD+
show the reaction diagram
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phenylpyruvate + NH3 + NADPH + H+ = phenylalanine + NADP+
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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5'-phospho-pyridoxyl-L-phenylalanine + H2O + O2 = pyridoxal 5'-phosphate + L-phenylalanine + H2O2
show the reaction diagram
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N-methyl-L-phenylalanine + O2 + H2O = L-phenylalanine + formaldehyde + H2O2
show the reaction diagram
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N-methyl L-phenylalanine + 2,6-dichlorophenolindophenol + H2O = L-phenylalanine + formaldehyde + reduced 2,6-dichlorophenolindophenol
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5-L-glutamyl-L-Phe + Gly-Gly = L-Phe + 5-L-glutamyl-Gly-Gly
show the reaction diagram
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L-aspartate + phenylpyruvate = oxaloacetate + L-phenylalanine
show the reaction diagram
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phenylpyruvate + 2-aminoadipate = L-phenylalanine + 2-oxoglutarate
show the reaction diagram
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L-alanine + phenylpyruvate = pyruvate + L-phenylalanine
show the reaction diagram
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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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benzoylformate + L-tyrosine = L-phenylalanine + 4-hydroxyphenylpyruvate
show the reaction diagram
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Phe-tRNA + H2O = Phe + tRNA
show the reaction diagram
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L-Phe benzyl ester + H2O = benzyl alcohol + L-phenylalanine
show the reaction diagram
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L-phenylalanine-7-amido-4-methylcoumarin + H2O = L-phenylalanine + 7-amino-4-methylcoumarin
show the reaction diagram
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Lys-Phe + H2O = Lys + Phe
show the reaction diagram
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L-Phe-Gly-Gly + H2O = L-Phe + Gly-Gly
show the reaction diagram
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L-phenylalanyl 4-nitroanilide + H2O = L-phenylalanine + 4-nitroaniline
show the reaction diagram
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L-Phe-7-amido-4-methylcoumarin + H2O = L-Phe + 7-amino-4-methylcoumarin
show the reaction diagram
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L-phenylalanyl 4-nitroanilide + H2O = L-phenylalanine + 4-nitroaniline
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L-Asp-L-Phe + H2O = L-Asp + L-Phe
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Phe-Phe-Phe + H2O = Phe-Phe + Phe
show the reaction diagram
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Tyr-Pro-Phe + H2O = Tyr-Pro + Phe
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N-carbobenzoxy-Ala-Ala-Phe-OH + H2O = N-carbobenzoxy-Ala-Ala + Phe
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Carbobenzoxy-Gly-Phe + H2O = Carbobenzoxy-Gly + Phe
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[3-(2-furylacryloyl)]-L-phenylalanyl-L-phenylalanine + H2O = [3-(2-furylacryloyl)]-L-phenylalanine + L-phenylalanine
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Phe-Ala + H2O = Phe + Ala
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Ac-Asp-Arg-Val-Tyr-Ile-His-Pro-Phe + H2O = Ac-Asp-Arg-Val-Tyr-Ile-His-Pro + L-phenylalanine
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pyroglutamyl-Phe + H2O = pyroglutamate + Phe
show the reaction diagram
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N-Formyl-Met-Phe + H2O = N-Formyl-Met + Phe
show the reaction diagram
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hippuryl-L-phenylalanine + H2O = hippuric acid + L-phenylalanine
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benzyloxycarbonyl-Glu-Phe + H2O = benzyloxycarbonyl-Glu + Phe
show the reaction diagram
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L-phenylalanine-isopropylester + H2O = L-phenylalanine + isopropanol
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N-benzyloxycarbonyl-Gly-Pro-Phe + H2O = N-benzyloxycarbonyl-Gly-Pro + L-Phe
show the reaction diagram
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L-phenylalanine amide + H2O = L-phenylalanine + NH3
show the reaction diagram
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L-Phe ethyl ester + H2O = L-Phe + ethanol
show the reaction diagram
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Benzyloxycarbonyl-Gly-Phe + H2O = Benzyloxycarbonyl-Gly + Phe
show the reaction diagram
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FVNQHLCGSHLVEALYLVCGERGFFYTPKA + H2O = FVNQHLCGSHL + VEA + Leu + Tyr + LVCGERGF + Phe + YTPKA
show the reaction diagram
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FVNQHLCGSHLVEALYLVCGERGFFYTPKA + H2O = L-Phe + VNQH + LCGSH + L-Leu + L-Val + L-Glu + L-Ala + L-Leu + L-Tyr + LVCG + ERG + L-Phe + L-Phe + YTPKA
show the reaction diagram
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Benzyloxycarbonyl-Gly-Phe + H2O = Benzyloxycarbonyl-Gly + Phe
show the reaction diagram
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FVNQHLCGSHLVEALYLVCGERGFFYTPKA + 6 H2O = FVNQHL + CGSHL + VEAL + L-Tyr + LVCGERGF + L-Phe + YTPKA
show the reaction diagram
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FVNQHLCGSHLVEALYLVCGERGFFYTPKA + H2O = FVNQHLCGSHL + VEAL + YLVCGERGF + L-Phe + YTPKA
show the reaction diagram
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benzyloxycarbonyl-Glu-Phe + H2O = benzyloxycarbonyl-Glu + Phe
show the reaction diagram
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Substance P + H2O = Arg-Pro-Lys-Pro-Gln-Gln + Phe + Phe-Gly + Leu-Met-NH2
show the reaction diagram
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Drosophila tachykinin-6 + H2O = QQR + Phe + ADFNSKFVAVR-amide
show the reaction diagram
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substance P fragment 2-11 + H2O = PKPQQ + Phe + Phe + GLM-NH2
show the reaction diagram
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L-phenylalanine amide + H2O = L-phenylalanine + NH3
show the reaction diagram
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N-phenylacetyl-Phe + H2O = phenylacetic acid + Phe
show the reaction diagram
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N-acetyl-L-phenylalanine + H2O = acetate + L-phenylalanine
show the reaction diagram
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jasmonoyl-L-phenylalanine + H2O = jasmonic acid + L-phenylalanine
show the reaction diagram
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N-acetylphenylalanine + H2O = acetate + phenylalanine
show the reaction diagram
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L-phenylalanine amide + H2O = L-Phe + NH3
show the reaction diagram
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N-benzoylphenylalanine + H2O = benzoate + phenylalanine
show the reaction diagram
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L-phenylalaninamide + H2O = L-phenylalanine + NH3
show the reaction diagram
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N-carbamoyl-L-phenylalanine + H2O = L-phenylalanine + CO2 + NH3
show the reaction diagram
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Nalpha-benzyloxycarbonyl-L-Phe + H2O = benzyl alcohol + CO2 + L-Phe
show the reaction diagram
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phenyl glycinenitrile + H2O = phenylalanine + NH3
show the reaction diagram
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5-L-glutamyl-L-phenylalanine = 5-oxoproline + L-phenylalanine
show the reaction diagram
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D-phenylalanine = L-phenylalanine
show the reaction diagram
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D-beta-phenylalanine = L-phenylalanine
show the reaction diagram
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ATP + H2O + L-phenylalanine/out = ADP + phosphate + L-phenylalanine/in
show the reaction diagram
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ATP + H2O + L-phenylalaninyl-[tyrosine-binding protein][side 1] = ADP + phosphate + L-phenylalanine[side 2] + [tyrosine-binding protein][side 1]
show the reaction diagram
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ATP + H2O + phenylalanine/out = ADP + phosphate + phenylalanine/in
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (33 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
stimulates conversion of prostaglandin G1 to H1
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slightly enhanced activity
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5 mM, 2.09fold activation
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slightly activating, mutants S187Y, S187F, S187C
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5 mM, activation of alkaline phosphatase grown in high phosphate medium to 168% of the control value
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essential for the formation of a homotrimer and for the HtrA2 serine protease activity
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1 mM, relative activity 140%
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expression increases in response to
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allosteric activator, activation above 0.1 mM
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exposure of 4-week old plants to phenylalanine increases enzyme activity as well as accumulation of coumarin-related compounds
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80 mM L-phenylalanine stimulates enzyme activity
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Inhibitor in Enzyme-catalyzed Reactions (169 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
long chain oxidase, 43% inhibition at 33 mM
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28% inhibition at 1 mM
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10 mM, 50% inhibition, competitive
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slight
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0.5 mM, 21% inhibition
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slight inhibition
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reductive amination of pyruvate, 10 mM, 28% inhibition
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20 mM, complete inhibition
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; pH 7.6, 30°C
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10% inhibition at 250 mM, with glycine
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10% inhibition at 250 mM
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slight inhibition
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hydroxylamine as substrate
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10 mM, at pH 6.5
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with 2 mM isoleucine as the substrate, 10 mM phenylalanine inhibits activity by 46%
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inhibitory above 0.14 mM
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2.5 mM, 10% inhibition
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5 mM, 87% residual activity
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33.5% activity at 1 mM
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noncompetitive
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competitive inhibition
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slight inhibition at 20 mM
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5 mM, 10% loss of activity
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weak
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (251 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.00305
-
-
0.022
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pH 6.2, 22°C
8.5
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pH 7.5, 25°C
10
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pH 8, mutant enzyme A12T/P13T/N34D/T109S/G261A/S285G/A293D/N297S
8.3
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pH 7.0, temperature not specified in the publication
590
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pH 8.0, 25°C
0.8
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at pH 8.5 and 25°C
0.404
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pH 7.5, 37°C, recombinant enzyme
8.002
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pH 8., 35°C
99.58
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pH 8.0, 30°C, mutant enzyme V83A

KM Value (548 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
2.4
-
-
0.0067
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pH 7.5, 26°C