Information on EC 1.13.11.16 - 3-carboxyethylcatechol 2,3-dioxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.13.11.16
-
RECOMMENDED NAME
GeneOntology No.
3-carboxyethylcatechol 2,3-dioxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + O2 = (2Z,4E,7E)-2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate
show the reaction diagram
(2)
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3-(2,3-dihydroxyphenyl)propanoate + O2 = (2Z,4E)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate
show the reaction diagram
(1)
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-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
3-phenylpropanoate and 3-(3-hydroxyphenyl)propanoate degradation to 2-oxopent-4-enoate
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cinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoate
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3-phenylpropionate degradation
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Phenylalanine metabolism
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
3-(2,3-dihydroxyphenyl)propanoate:oxygen 1,2-oxidoreductase (decyclizing)
An iron protein. This enzyme catalyses a step in the pathway of phenylpropanoid compounds degradation.
CAS REGISTRY NUMBER
COMMENTARY hide
105503-63-7
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene mhpB
SwissProt
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2,3-dihydroxycinnamic acid + O2
2-hydroxy-6-oxonona-2,4,7-trienoate
show the reaction diagram
2,3-dihydroxyphenoxyacetic acid + O2
2-hydroxyhexa-2,4-dienoic acid-6-carboxymethylester
show the reaction diagram
-
-
-
-
?
2,3-dihydroxyphenylpropionic acid + O2
2-hydroxy-6-oxonona-dienoate
show the reaction diagram
3-(2,3-dihydroxyphenyl)propionate + O2
2-hydroxy-6-oxonona-2,4-diene-1,9-dioate
show the reaction diagram
3-ethylcatechol + O2
2-hydroxy-6-oxoocta-2,4-dienoate
show the reaction diagram
3-methylcatechol + O2
2-hydroxy-6-oxohepta-2,4-dienoate
show the reaction diagram
3-phenethylcatechol + O2
2-hydroxy-6-oxo-8-phenylocta-2,4-dienoate
show the reaction diagram
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-
-
-
?
3-propylcatechol + O2
2-hydroxy-6-oxonona-2,4-dienoate
show the reaction diagram
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-
-
-
?
catechol + O2
2-hydroxy-6-oxohexa-2,4-dienoate
show the reaction diagram
meta-ring-cleavage
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-
?
methyl-(2,3-dihydroxyphenyl)propionate + O2
2-hydroxy-6-oxonona-2,4-dienoic acid-9-methylester
show the reaction diagram
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-
?
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
3-(2,3-dihydroxyphenyl)propionate + O2
2-hydroxy-6-oxonona-2,4-diene-1,9-dioate
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-(3,4-dihydroxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
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over 90% inhibition at 0.25 mM
diethyl dicarbonate
N-benzyl-3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide
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25% inhibition at 0.25 mM
p-hydroxymercuribenzoate
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.014 - 0.036
2,3-dihydroxycinnamic acid
0.3
2,3-dihydroxyphenoxyacetic acid
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-
0.0071 - 0.026
3-(2,3-dihydroxyphenyl)propionate
0.059 - 0.185
3-ethylcatechol
0.09 - 0.13
3-methylcatechol
0.094
3-phenethylcatechol
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-
0.154
3-propylcatechol
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0.72
catechol
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0.037
methyl-2,3-dihydroxyphenylpropionate
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
29
3-(2,3-dihydroxyphenyl)propionate
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3.6
3-methylcatechol
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2
catechol
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.11
2-(3,4-dihydroxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
Rhodococcus jostii
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pH 7.5, 37°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.3
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2,3-dihydroxyphenylproponic acid
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
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assay at
8 - 9.5
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
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assay at
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
36000
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4 * 36000, SDS-PAGE
70000
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gel filtration
134000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
tetramer
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4 * 36000, SDS-PAGE
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
activity stable in crude extract, inactive apoenzyme stable, can be re-activated by treatment with Fe2+ and ascorbate, irreversible apoenzyme activity loss if stored in completely Fe2+-free buffer, re-activated holoenzyme unstable
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Show AA Sequence (1059 entries)
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