1.13.11.15: 3,4-dihydroxyphenylacetate 2,3-dioxygenase
This is an abbreviated version!
For detailed information about 3,4-dihydroxyphenylacetate 2,3-dioxygenase, go to the full flat file.
Word Map on EC 1.13.11.15
-
1.13.11.15
-
extradiol
-
catecholate
-
4-nitrocatechol
-
fuscum
-
brevibacterium
-
globiformis
-
manganese-dependent
-
ring-cleaving
-
extradiol-cleaving
-
second-sphere
-
monoanionic
-
hydroperoxo
-
4-hydroxyphenylacetate
-
superoxo
-
alkylperoxo
-
feiii-superoxo
-
manganeseii
-
ortho-dihydroxylated
-
side-on
-
crystallo
- 1.13.11.15
-
extradiol
-
catecholate
- 4-nitrocatechol
- fuscum
-
brevibacterium
- globiformis
-
manganese-dependent
-
ring-cleaving
-
extradiol-cleaving
-
second-sphere
-
monoanionic
-
hydroperoxo
- 4-hydroxyphenylacetate
-
superoxo
-
alkylperoxo
-
feiii-superoxo
-
manganeseii
-
ortho-dihydroxylated
-
side-on
-
crystallo
Reaction
Synonyms
2,3-HPCD, 3,4-dihydroxyphenylacetic acid 2,3-dioxygenase, Bf 2,3-HPCD, DHPAO, Fe-HPCD, Fe-MndD, FeHPCD, homoprotocatechuate 2,3 dioxygenase, homoprotocatechuate 2,3-dioxygenase, homoprotocatechuate dioxygenase, HPADO, HPC 2,3-dioxygenase, HPC dioxygenase, HPCA 2,3-dioxygenase, HPCD, Mn(II)-dependent 3,4-dihydroxyphenylacetate 2,3-dioxygenase, Mn-HPCD, Mn-MndD, MndD, MnHPCD, oxygenase, homoprotocatechuate 2,3-di-, PaDHPAO
ECTree
1.13.11.15 3,4-dihydroxyphenylacetate 2,3-dioxygenaseAdvanced search results
results (
results (Results
in table
3
2227
84
72
14
49
Substrates Products
Substrates Products on EC 1.13.11.15 - 3,4-dihydroxyphenylacetate 2,3-dioxygenase
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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
2,3-dihydroxybenzoate + O2
CO2 + alpha-hydroxymuconic semialdehyde
-
-
mutant H200F produces alpha-carboxy-cis,cis-muconic acid
-
?
3,4 dihydroxyphenylacetate + O2
1-carboxymethyl-4-hydroxy-cis-muconic semialdehyde
-
-
-
-
?
3,4-dihydroxyphenylacetate + O2
1-carboxymethyl-4-hydroxy-cis-muconic semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethyl-cis,cis-muconate semialdehyde
-
-
-
-
?
3-(3,4-dihydroxyphenyl)-DL-alanine + O2
(2E,4Z)-7-amino-5-formyl-2-hydroxyocta-2,4-dienedioic acid
-
-
-
-
?
4-nitrocatechol + O2
(2Z,4Z)-2-hydroxy-4-nitro-6-oxohexa-2,4-dienoate
-
-
-
?
4-nitrocatechol + O2
(2Z,4Z)-2-hydroxy-5-nitro-6-oxohexa-2,4-dienoate
-
-
-
?
N-formyl-3-(3,4-dihydroxyphenyl)-DL-alanine + O2
(2E,4Z)-5-formyl-7-(formylamino)-2-hydroxyocta-2,4-dienedioic acid
-
-
-
-
?
3,4-dihydroxybenzoic acid + O2
2-hydroxy-5-carboxymuconate semialdehyde
-
0.58% of the activity with 3,4-dihydroxyphenylacetate
-
-
?
3,4-dihydroxybenzoic acid + O2
2-hydroxy-5-carboxymuconate semialdehyde
-
-
-
-
?
3,4-dihydroxybenzoic acid + O2
2-hydroxy-5-carboxymuconate semialdehyde
-
0.125% of the activity with 3,4-dihydroxyphenylacetate
-
-
?
3,4-dihydroxymandelate + O2
?
Arthrobacter synephrinum
-
50% of the activity with 3,4-dihydroxyphenylacetate
-
-
?
3,4-dihydroxymandelate + O2
?
-
14% of the activity with 3,4-dihydroxyphenylacetate
-
-
?
3,4-dihydroxymandelate + O2
?
-
83% of the activity with 3,4-dihydroxyphenylacetate
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
enzyme is induced by 4-hydroxyphenylacetate
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
enzyme is involved in the meta-cleavage pathway for the degradation of 4-hydroxyphenylacetic acid
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
enzyme is involved in the meta-cleavage pathway for the degradation of 4-hydroxyphenylacetic acid
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
enzyme is involved in catabolism of L-Tyr
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
Arthrobacter synephrinum
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
enzyme catalyzes the estradiol cleavage of catechols
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
key ring cleavage step in metabolism of 3,4-dihydroxyphenylacetate
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
proximal extradiol cleavage of the aromatic ring of the substrate
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
Fe2+-containing homoprotocatechuate 2,3-dioxygenase, FeHPCD, activates O2 to catalyze the aromatic ring opening of homoprotocatechuate. O2 activation steps for extradiol dioxygenases, mechanism, overview
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
Mössbauer spectra of the reaction intermediates trapped by rapid freeze quench show that both intermediates contain Fe2+. The lack of a chromophore characteristic of a quinone or semiquinone form of HPCA, the presence of Fe2+, and the low O2 affinity suggests that is an HPCA-FeII-O2 complex with little electron delocalization onto the O2
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
substrates homoprotocatechuate and O2 bind to the Fe2+ of homoprotocatechuate 2,3-dioxygenase in adjacent coordination sites. Transfer of an electron(s) from 3,4-dihydroxyphenylacetate to O2 via the iron is proposed to activate the substrates for reaction with each other to initiate aromatic ring cleavage. Oxygen is bound as a (hydro)peroxo ligand. At least four intermediates form following addition of O2 with a pre-formed enzyme-substrate complex, different intermediate formation in mutant H200N, Mössbauer spectral analysis, overview
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
inducible enzyme
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
enzyme is involved in catabolism of L-Tyr
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
catabolism of 3-hydroxyphenylacetate and 4-hydroxyphenylacetate by 3,4-dihydroxyphenylacetate pathway
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
enzyme is involved in catabolism of L-Tyr
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
enzyme is involved in catabolism of biogenic amines
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
the enzyme catalyzes the extradiol ring cleavage of 3,4-dihydroxyphenylacetate (DHPA) by incorporation of molecular oxygen to yield 5-carboxymethyl-2-hydroxymuconate semialdehyde (CHMS). O2 insertion occurs through the substrate-alkylperoxo-Fe(II) intermediate
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
the enzyme catalyzes the extradiol ring cleavage of 3,4-dihydroxyphenylacetate (DHPA) by incorporation of molecular oxygen to yield 5-carboxymethyl-2-hydroxymuconate semialdehyde (CHMS). O2 insertion occurs through the substrate-alkylperoxo-Fe(II) intermediate
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
induced by 3,4-dihydroxyphenylacetate
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
induced by 3-chlorophenylacetate
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
induced by 3-chlorophenylacetate
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
2-hydroxy-5-carboxymethylmuconate semialdehyde
-
-
-
?
3,4-dihydroxyphenylacetate + O2
?
-
1 mM, assay at pH 7.8, 23°C
-
-
?
3,4-dihydroxyphenylpropionate + O2
2-hydroxy-5-carboxyethylmuconate semialdehyde
Arthrobacter synephrinum
-
4% of the activity with 3,4-dihydroxyphenylacetate
-
-
?
3,4-dihydroxyphenylpropionate + O2
2-hydroxy-5-carboxyethylmuconate semialdehyde
-
5% of the activity with 3,4-dihydroxyphenylacetate
-
-
?
3,4-dihydroxyphenylpropionate + O2
2-hydroxy-5-carboxyethylmuconate semialdehyde
-
58% of the activity with 3,4-dihydroxyphenylacetate
-
-
?
3,4-dihydroxyphenylpropionate + O2
2-hydroxy-5-carboxyethylmuconate semialdehyde
-
2.86% of the activity with 3,4-dihydroxyphenylacetate
-
-
?
3,4-dihydroxyphenylpropionate + O2
2-hydroxy-5-carboxyethylmuconate semialdehyde
-
low activity
-
-
?
4-nitrocatechol + O2
?
-
not the native substrate for HPCD, it is cleaved in a similar fashion as the natural substrate, homoprotocatechuate, 4-nitrocatechol exhibits characteristic visible absorption bands that are sensitive to its ionization and oxidation states, suitable for spectral substrate binding and reaction mechanism analysis
-
-
?
additional information
?
-
-
LB400 cells grown with 3-hydroxyphenylacetate degrade homoprotocatechuate and show homoprotocatechuate 2,3-dioxygenase activity
-
-
?
additional information
?
-
-
poor or no activity with 3,4-dihydroxyphenylpropionate, 3,4-dihydroxybenzoate, 4-hydroxyphenylacetate, 4-hydroxybenzoate, 4-hydroxyphenylpropionate, 4-hydroxy-3-methoxyphenylacetate, and 4-nitrocatechol
-
-
?
additional information
?
-
-
poor or no activity with 3,4-dihydroxyphenylpropionate, 3,4-dihydroxybenzoate, 4-hydroxyphenylacetate, 4-hydroxybenzoate, 4-hydroxyphenylpropionate, 4-hydroxy-3-methoxyphenylacetate, and 4-nitrocatechol
-
-
?
additional information
?
-
-
very low activity with various 4-substituted catechols
-
-
?
