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Information on EC 5.3.3.12 - L-dopachrome isomerase
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5.3.3.12 L-dopachrome isomeraseIUBMB Comments
A zinc enzyme. Stereospecific for L-dopachrome. Dopachrome methyl ester is a substrate, but dopaminochrome (2,3-dihydroindole-5,6-quinone) is not (see also EC 4.1.1.84, D-dopachrome decarboxylase).
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Word Map
- 5.3.3.12
- tyrosinase
- melanin
- melanoma
-
tyrosinase-related
- melanocyte
-
melanogenesis
-
melanogenic
-
microphthalmia-associated
- melanosomes
- hyperpigmentation
- protein-2
-
anti-melanogenic
-
whitening
-
melanogenesis-related
- microphthalmia
-
pigmentary
-
dhica
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melanoma-associated
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amelanotic
- trp1
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melanoblast
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skin-whitening
-
melanocyte-specific
- 5,6-dihydroxyindole
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depigment
-
pheomelanin
- vitiligo
-
depigmentation
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5,6-dihydroxyindole-2-carboxylic
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crest-derived
-
chemokine-like
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tautomerization
-
melanin-producing
-
cloudman
-
premelanosome
- arbutin
- medicine
- drug development
- pmel17
- alpha-msh
-
alpha-melanocyte
-
anti-melanogenesis
-
mart-1
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
trp-2, dopachrome tautomerase, d-dopachrome tautomerase, macrophage inhibitory factor, macrophage migration-inhibitory factor, dopachrome conversion factor, tyrosine-related protein 2, dopachrome oxidoreductase, dopachrome-rearranging enzyme, brown (b) locus protein, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
brown (b) locus protein
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-
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D-dopachrome isomerase
D-dopachrome tautomerase
D-DT
DCF
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-
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DCT
DDT
dopachrome conversion factor
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-
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dopachrome delta-isomerase
dopachrome DELTA7-DELTA2-isomerase
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dopachrome oxidoreductase
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dopachrome tautomerase
dopachrome-rearranging enzyme
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isomerase, dopachrome DELTA-
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L-dopachchrome-methyl ester tautomerase
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macrophage inhibitory factor
Macrophage migration inhibitory factor
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MIF
SLATY locus protein
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TRP2
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tyrosine-related protein 2
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DCT
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-
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dopachrome delta-isomerase
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-
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dopachrome tautomerase
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-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
L-dopachrome = 5,6-dihydroxyindole-2-carboxylate
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-
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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
intramolecular oxidoreduction
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-
-
-
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SYSTEMATIC NAME
IUBMB Comments
L-dopachrome keto-enol isomerase
A zinc enzyme. Stereospecific for L-dopachrome. Dopachrome methyl ester is a substrate, but dopaminochrome (2,3-dihydroindole-5,6-quinone) is not (see also EC 4.1.1.84, D-dopachrome decarboxylase).
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CAS REGISTRY NUMBER
COMMENTARY
130122-81-5
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
L-3,4-dihydroxyphenylalanine methyl ester
methyl 3-(3,4-dioxocyclohexa-1,5-dien-1-yl)-L-alaninate
L-alpha-methyldopachrome
5,6-dihydroxy-2-methyl-2,3-dihydro-1H-indole-2-carboxylic acid
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-
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?
L-dopachrome
5,6-dihydroxyindole-2-carboxylic acid
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i.e. 2-carboxy-2,3-dihydroindole-5,6-quinone, the enzyme is strictly specific for the L-enantiomer. The N-terminal Pro is crucial for tautomerase activity
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-
?
dopachrome
5,6-dihydroxyindole-2-carboxylate
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highly stereospecific for L-dopachrome
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?
dopachrome
5,6-dihydroxyindole-2-carboxylate
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highly stereospecific for L-dopachrome
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?
L-3,4-dihydroxyphenylalanine methyl ester
methyl 3-(3,4-dioxocyclohexa-1,5-dien-1-yl)-L-alaninate
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i.e. L-3,4-dihydroxyphenylalanine methyl ester hydrochloride, the catalytic residue is N-terminal Pro1
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-
r
L-3,4-dihydroxyphenylalanine methyl ester
methyl 3-(3,4-dioxocyclohexa-1,5-dien-1-yl)-L-alaninate
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the catalytic residue is N-terminal Pro1
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-
r
L-dopachrome
5,6-dihydroxyindole-2-carboxylate
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Dct isomerizes the intermediate dopachrome to 5,6-dihydroxyindole-2-carboxylic acid, DHICA, and influences the proportion of DHICA monomer incorporated into the 5,6-dihydroxyindole, DHI, polymer in eumelanin
DHICA monomers are required to incorporate into the DHI polymer backbone of eumelanin. DHICA exhibits a potent hydroxyl radical-scavenging activity when bound to melanin, while DHI-melanin does not
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?
L-dopachrome
5,6-dihydroxyindole-2-carboxylate
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Dct isomerizes the intermediate dopachrome to 5,6-dihydroxyindole-2-carboxylic acid, DHICA, and influences the proportion of DHICA monomer incorporated into the 5,6-dihydroxyindole, DHI, polymer in eumelanin
DHICA monomers are required to incorporate into the DHI polymer backbone of eumelanin. DHICA exhibits a potent hydroxyl radical-scavenging activity when bound to melanin, while DHI-melanin does not
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?
additional information
?
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existence of a common mechanism underlying radio- and chemoresistance, which is mediated by the enzyme
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?
additional information
?
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role of enzyme in cytoprotection by preventing the production of atoxic melanin precursor, 5,6-dihydroxyindole
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?
additional information
?
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isoforms of enzyme may play a part in the normal pathway of melamin biosynthesis
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?
additional information
?
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WM35-wild-type and WM35-C2 cells, containing overexpressed TRP-2 enzyme are incubated with various H2O2 concentrations to determine the survival rate. TRP-2 reduces oxidative stress-induced toxicity of WM35-C2 cells compared to the wild-type cells, at 300 microM H2O2 30% decrease of cell sensitivity. TRP-2 protects genomic DNA from oxidative stress damage: in wild-type WM35 cells the damaging effect on DNA is visible at 50 microM H2O2. WM35 cells containing the overexpressed TRP-2 show DNA damage after treatment with 100 microM H2O2. The overexpression of TRP-2 in HEK-293 cells shows no improvement of the cell sensitivity to oxidative stress
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?
additional information
?
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MIF is a 12 kDa protein with an enzymatic keto-enol tautomerase activityMIF is a homotrimeric multifunctional proinflammatory cytokine. Binding of MIF to its receptor, CD74, overview
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-
?
additional information
?
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MIF is a homotrimeric multifunctional proinflammatory cytokine. Binding of MIF to its receptor, CD74, overview
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?
additional information
?
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the MIF protein is multifunctional, exhibiting besides its L-dopachrome tautomerase activity, e.g. also phenylpyruvate tautomerase activity, EC 5.3.2.1, and thioredoxin-like function, or its cytokine function, overview
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?
additional information
?
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no substrate: L-dopachrome methyl ester, dopaminochrome, adrenochrome
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-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
L-dopachrome
5,6-dihydroxyindole-2-carboxylate
-
Dct isomerizes the intermediate dopachrome to 5,6-dihydroxyindole-2-carboxylic acid, DHICA, and influences the proportion of DHICA monomer incorporated into the 5,6-dihydroxyindole, DHI, polymer in eumelanin
DHICA monomers are required to incorporate into the DHI polymer backbone of eumelanin. DHICA exhibits a potent hydroxyl radical-scavenging activity when bound to melanin, while DHI-melanin does not
-
?
L-dopachrome
5,6-dihydroxyindole-2-carboxylate
-
Dct isomerizes the intermediate dopachrome to 5,6-dihydroxyindole-2-carboxylic acid, DHICA, and influences the proportion of DHICA monomer incorporated into the 5,6-dihydroxyindole, DHI, polymer in eumelanin
DHICA monomers are required to incorporate into the DHI polymer backbone of eumelanin. DHICA exhibits a potent hydroxyl radical-scavenging activity when bound to melanin, while DHI-melanin does not
-
?
additional information
?
-
-
existence of a common mechanism underlying radio- and chemoresistance, which is mediated by the enzyme
-
-
?
additional information
?
-
-
role of enzyme in cytoprotection by preventing the production of atoxic melanin precursor, 5,6-dihydroxyindole
-
-
?
additional information
?
-
-
isoforms of enzyme may play a part in the normal pathway of melamin biosynthesis
-
-
?
additional information
?
-
-
MIF is a 12 kDa protein with an enzymatic keto-enol tautomerase activityMIF is a homotrimeric multifunctional proinflammatory cytokine. Binding of MIF to its receptor, CD74, overview
-
-
?
additional information
?
-
-
MIF is a homotrimeric multifunctional proinflammatory cytokine. Binding of MIF to its receptor, CD74, overview
-
-
?
additional information
?
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the MIF protein is multifunctional, exhibiting besides its L-dopachrome tautomerase activity, e.g. also phenylpyruvate tautomerase activity, EC 5.3.2.1, and thioredoxin-like function, or its cytokine function, overview
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Iron
Zinc
additional information
additional information
-
metal-containing enzyme, possibly with iron at its catalytic center
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2-oxo-4-phenyl-3-butynoate
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a potent site-directed irreversible inhibitor of the phenyl pyruvate tautomerase activity
3,6-dihydroxy-1-methyl-5-oxo-3,5-dihydro-2H-indolium
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a dopachrome derivative, 98% inhibition at 0.5 mM, mechanism of action, overview
3,6-dihydroxy-2-methyl-2,3-dihydro-5H-indol-5-one
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a dopachrome derivative, 92% inhibition at 0.5 mM, mechanism of action, overview
3,6-dihydroxy-5-oxo-3,5-dihydro-2H-indole-2-carboxylic acid
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a dopachrome derivative, complete inhibition at 0.5 mM, mechanism of action, overview
6-hydroxy-2-methyl-5-oxo-3,5-dihydro-2H-indole-2-carboxylic acid
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a dopachrome derivative, 35% inhibition at 0.5 mM, mechanism of action, overview; a dopachrome derivative, L-derivative, 29% inhibition at 0.5 mM, mechanism of action, overview
Benzyl isothiocyanate
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specific inhibition of MIF tautomerase activity is mediated by selective modification of the N-terminal proline
Isothiocyanate
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inhibits tautomerase activity of MIF. Modification and inhibition of MIF is not involved in the induction of phase 2 gene expression in response to isothiocyanate treatment
methyl 6-hydroxy-2-methyl-5-oxo-3,5-dihydro-2H-indole-2-carboxylate
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a dopachrome derivative, 34% inhibition at 0.5 mM, mechanism of action, overview; a dopachrome derivative, 45% inhibition at 0.5 mM, mechanism of action, overview
additional information
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design and synthesis of irreversible isothiocyanate-based inhibitors of MIF, inhibitory potencies and inhibition mechanism, overview
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additional information
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there exist several classes of inhibitors that are active against MIF tautomerase activity, overview
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
L-ascorbic acid
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enzyme activity depends on the presence of a reducing compound to a final concentration of 0.1mM
L-cysteine
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enzyme activity depends on the presence of a reducing compound to a final concentration of 0.1mM
N-acetyl-L-cysteine
-
enzyme activity depends on the presence of a reducing compound to a final concentration of 0.1mM
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.8
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4.8 - 8.2
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pH 4.8: about 40% of maximum activity, pH 8.2: about 55% of maximum activity
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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peripheral blood mononuclear cells, expression in wild-type but no enzyme expression in vitiligo patients, overview
brenda
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blocking endogenous enzyme by RNAi decreases proliferation of embryoic cortical neural progenitor cells
brenda
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overexpression of enzyme in subventricular zone cells of adult mice significantly increases the number of cells, whereas silencing Dct enzyme by RNAi decreases the cell number
brenda
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enzyme is expressed in all layers of the dorsal telencephalon in E10.5
brenda
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at E15.5 and E17.5, enzyme expression is primarily localized to the ventricular zone
brenda
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measuring of the spatial and temporal pattern of enzyme expression in vivo during neocortical neurogenesis. Enzyme is expressed in all layers of the dorsal telencephalon in E10.5. At E15.5 and E17.5, expression is primarily localized to the ventricular zone. Blocking endogenous enzyme by RNAi decreases proliferation of embryoic cortical neural progenitor cells. In adult brain, strong expression is observed in rostral migratory stream and septum. Overexpression of enzyme in subventricular zone cells of adult mice significantly increases the number of cells, whereas silencing Dct enzyme by RNAi decreases the cell number
brenda
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preparation of single-cell suspensions of the tail skin
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brenda