Ligand L-Dopa

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Basic Ligand Information

Molecular Structure
Picture of L-Dopa (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H11NO4
L-Dopa
WTDRDQBEARUVNC-LURJTMIESA-N
Synonyms:
(2S)-2-am'ino-3-(3,'4-dihydro'xyphenyl)'propanoic' acid, 3,4-dihydroxy-L-Phe, 3,4-dihydroxy-L-phenylalanine, 3,4-dihydroxy L-phenylalanine, 3,4-dihydroxyphenyl-L-Ala, 3,4-dihydroxyphenyl-L-alanine, 3,4-dihydroxyphenylalanine, 3-(3,4-dihydroxyphenyl)-L-Ala, 3-(3,4-dihydroxyphenyl)-L-alanine, 3-hydroxy-L-tyrosine, beta-(3,4-dihydroxyphenyl)-L-alanine, dihydroxy-L-phenylalanine, dihydroxyphenylalanine, Dopa, L-(3,4-dihydroxy)phenylalanine, L-(3,4-dihydroxyphenyl)alanine, L-3,4-dihydroxyphenylalanine, L-3-4 dihydroxyphenylalanine, L-3-hydroxytyrosine, L-beta-(3,4-dihydroxyphenyl)alanine, L-beta-3,4-dihydroxyphenylalanine, L-dihydroxy-phenylalanine, L-dihydroxyphenylalanine, levo-dopa, levodopa


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

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (101 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
DOPA + O2 = ? + H2O
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L-DOPA + O2 = ?
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3,4-dihydroxy-L-phenylalanine + O2 = 4-(L-alanin-3-yl)-2-hydroxy-cis,cis-muconate 6-semialdehyde
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3,4-dihydroxy-L-phenylalanine + O2 = 5-(L-alanin-3-yl)-2-hydroxy-cis,cis-muconate 6-semialdehyde
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L-DOPA + O2 = ?
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L-DOPA + O2 = ?
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L-Dopa + O2 + H2O = 3,4-dihydroxyphenylacetaldehyde + CO2 + NH3 + H2O2
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L-Dopa + O2 + H2O = 3,4-dihydroxy-phenylacetaldehyde + CO2 + NH3 + H2O2
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L-Dopa = dopamine + CO2
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L-3-4 dihydroxyphenylalanine + H2O = catechol + pyruvate + NH3
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In Vivo Product in Enzyme-catalyzed Reactions (67 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

Substrate in Enzyme-catalyzed Reactions (309 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-DOPA + O2 = ?
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L-DOPA + O2 = ?
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-
L-Dopa + H2O2 = ?
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L-DOPA + H2O2 + H+ = ?
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beta-(3,4-dihydroxyphenyl)-L-alanine + H2O2 = ? + H2O
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L-3,4-dihydroxyphenylalanine + H2O2 = ?
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3,4-dihydroxy-L-phenylalanine + O2 = 4-(L-alanin-3-yl)-2-hydroxy-cis,cis-muconate 6-semialdehyde
show the reaction diagram
-
3,4-dihydroxy-L-phenylalanine + O2 = 5-(L-alanin-3-yl)-2-hydroxy-cis,cis-muconate 6-semialdehyde
show the reaction diagram
-
L-(3,4-dihydroxy)phenylalanine + ? = ?
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L-DOPA + H2O + O2 = 3,4-dihydroxyphenylpyruvate + NH3 + H2O2
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L-Dopa + H2O + 2 cytochrome b = 3-(3,4-dihydroxyphenyl)-pyruvate + NH3 + 2 reduced cytochrome b
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L-DOPA + O2 = ?
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L-3,4-dihydroxyphenylalanine + 2-oxoglutarate = 3-(3,4-dihydroxyphenyl)-2-oxopropanoate + L-glutamate
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3,4-dihydroxyphenylalanine + 2-oxoglutarate = 3-(3,4-dihydroxyphenyl)-2-oxopropanoate + L-glutamate
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L-DOPA + 4-(methylsulfanyl)-2-oxobutanoate = ?
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DOPA + H2O = ?
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L-Dopa + O2 + H2O = 3,4-dihydroxyphenylacetaldehyde + CO2 + NH3 + H2O2
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3,4-Dihydroxyphenylalanine = Dopamine + CO2
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3,4-Dihydroxyphenylalanine = Dopamine + CO2
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3,4-dihydroxyphenylalanine = ?
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L-3,4-dihydroxyphenylalanine = 3-amino-3-(3,4-dihydroxyphenyl)propanoate
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ATP + L-3,4-dihydroxyphenylalanine + tRNATyr = AMP + L-3,4-dihydroxyphenylalanine-tRNATyr + diphosphate
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ATP + detyrosinated alpha-tubulin + L-DOPA = ?
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Product in Enzyme-catalyzed Reactions (163 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-tyrosine + ascorbate + O2 = L-dopa + dehydroascorbate + H2O
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (38 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
substitutes for tyrosine to stimulate in vitro HydA1 activation, improves HydA1 maturation 4fold
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L-DOPA treatment (20-200 microM) increases the levels of dopamine by 226%-504% after 3-6 h of treatment and enhances the activities of tyrosine hydroxylase and aromatic L-amino acid decarboxylase
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up-regulation of enzyme upon exposure to L-dopa and tetrahydropapaveroline
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activates GSK-3beta at high dose
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activates mutant form lacking START domain
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L-DOPA treatment (20-200 microM) increases the levels of dopamine by 226%-504% after 3-6 h of treatment and enhances the activities of tyrosine hydroxylase and aromatic L-amino acid decarboxylase
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enhances nigral mitochondrial complex I expression and activity. Significant increase at 6 h, with maximal values at 24 h, compared with control animals, in absence of concomitant changes in the expression or activity of complex IV
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Inhibitor in Enzyme-catalyzed Reactions (49 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.1 mM and 1 mM, 39% and 94% inhibition of benzaldehyde oxidation, respectively
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slight inhibition
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inactivated by a Pictet-Spengler reaction between the cofactor and 3,4-dihydroxyphenyl-L-alanine, on treatment with excess pyridoxal-5'-phosphate the inactivated enzymes recovers over 80% of the original activity
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3D Structure of Enzyme-Ligand-Complex (PDB) (20 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (73 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.066
-
at pH 7.0 and 55°C
0.066
-
in 50 mM sodium phosphate, pH 7.0, 30°C
0.27
-
at pH 7.5 and 37°C
1.29
-
mutant S354G, pH 6.8, 37°C
0.3
-
pH 8.0, 30°C, wild-type enzyme
0.0067
-
-

KM Value (186 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
5.5
-
at pH 7.0 and 55°C
5.5
-
in 50 mM sodium phosphate, pH 7.0, 30°C
1.39
-
-
0.014
-
pH 7.5, 38°C
1.67
-
-
0.19
-
at pH 7.5 and 37°C
6
-
pH 8.0, 37°C
41
-
pH 8.2, 37°C
26
-
pH 7.9, 37°C
0.76
-
pH 9.3, 37°C
0.13
-
mutant S354G, pH 6.8, 37°C
0.21
-
-
0.4
-
pH 8.0, 30°C, wild-type enzyme
1.54
-
-
0.186
-
-

Ki Value (7 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
72
-
-
0.47
-
-
0.26
-
-
10
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wild-type enzyme, the data of initial velocity for decarboxylation of L-dopa versus substrate concentration curiously exhibit a substrate-inhibition pattern that requires a modified version of the Michaelis-Menten equation.

IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE

References & Links