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EC Tree
IUBMB Comments Involved in the meta-cleavage pathway for the degradation of phenols, modified phenols and catechols. The enzyme has been reported to accept multiple tautomeric forms [1-4]. However, careful analysis of the stability of the different tautomers, as well as characterization of the enzyme that produces its substrate, EC 5.3.2.6, 2-hydroxymuconate tautomerase, showed that the actual substrate for the enzyme is (3E)-2-oxohex-3-enedioate .
The enzyme appears in viruses and cellular organisms
Synonyms
4-oxalocrotonate decarboxylase, oxalocrotonate decarboxylase,
more
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4-oxalocrotonate decarboxylase
Decarboxylase, 4-oxalocrotonate
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Oxalocrotonate decarboxylase
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4-OD
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4-oxalocrotonate decarboxylase
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4-oxalocrotonate decarboxylase
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4OD
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NahK
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(3E)-2-oxohex-3-enedioate = 2-oxopent-4-enoate + CO2
(3E)-2-oxohex-3-enedioate = 2-oxopent-4-enoate + CO2
mechanism
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(3E)-2-oxohex-3-enedioate = 2-oxopent-4-enoate + CO2
mechanism
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(3E)-2-oxohex-3-enedioate = 2-oxopent-4-enoate + CO2
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, , , , , , , , , Benzoate degradation , Microbial metabolism in diverse environments , phenol degradation
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(3E)-2-oxohex-3-enedioate carboxy-lyase (2-oxopent-4-enoate-forming)
Involved in the meta-cleavage pathway for the degradation of phenols, modified phenols and catechols. The enzyme has been reported to accept multiple tautomeric forms [1-4]. However, careful analysis of the stability of the different tautomers, as well as characterization of the enzyme that produces its substrate, EC 5.3.2.6, 2-hydroxymuconate tautomerase, showed that the actual substrate for the enzyme is (3E)-2-oxohex-3-enedioate [4].
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(3E)-2-oxohex-3-enedioate
2-oxopent-4-enoate + CO2
2-oxo-3-hexenedioate
2-oxopent-4-enoate + CO2
4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
(3E)-2-oxohex-3-enedioate
2-oxopent-4-enoate + CO2
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?
(3E)-2-oxohex-3-enedioate
2-oxopent-4-enoate + CO2
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2-oxo-3-hexenedioate
2-oxopent-4-enoate + CO2
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4-OD and vinylpyruvate hydratase form a complex, 2-hydroxy-2,4-pentadienoate is the product of 4-OD and 2-oxo-4-pentenoate results from a vinylpyruvate hydratase-catalyzed process
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2-oxo-3-hexenedioate
2-oxopent-4-enoate + CO2
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4-OD and vinylpyruvate hydratase form a complex, 2-hydroxy-2,4-pentadienoate is the product of 4-OD and 2-oxo-4-pentenoate results from a vinylpyruvate hydratase-catalyzed process
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4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
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4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
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4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
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4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
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4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
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4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
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4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
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4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
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4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
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2-hydroxy-2,4-pentanedienoate is an intermediate
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4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
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4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
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4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
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4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
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4-Oxalocrotonate
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but not p-cresol
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4-Oxalocrotonate
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strain 345: induced by growth with m-toluate, strain RA1012: induced by growth with p-cresol, but not m-toluate
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4-Oxalocrotonate
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but not p-cresol
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4-Oxalocrotonate
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strain 345: induced by growth with m-toluate, strain RA1012: induced by growth with p-cresol, but not m-toluate
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4-Oxalocrotonate
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but not p-cresol
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4-Oxalocrotonate
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strain 345: induced by growth with m-toluate, strain RA1012: induced by growth with p-cresol, but not m-toluate
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4-Oxalocrotonate
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enzyme of the phenol/3,4-dimethylphenol catabolic pathway
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4-Oxalocrotonate
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enzyme of the phenol/3,4-dimethylphenol catabolic pathway
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4-Oxalocrotonate
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enzyme is involved in the meta-cleavage pathway for catechols
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4-Oxalocrotonate
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phenol and m-cresol are inducers
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4-Oxalocrotonate
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enzyme is involved in the meta-cleavage pathway for catechols
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4-Oxalocrotonate
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phenol and m-cresol are inducers
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4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
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4-Oxalocrotonate
2-Oxopent-4-enoate + CO2
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4-Oxalocrotonate
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but not p-cresol
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4-Oxalocrotonate
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strain 345: induced by growth with m-toluate, strain RA1012: induced by growth with p-cresol, but not m-toluate
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4-Oxalocrotonate
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but not p-cresol
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4-Oxalocrotonate
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strain 345: induced by growth with m-toluate, strain RA1012: induced by growth with p-cresol, but not m-toluate
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4-Oxalocrotonate
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but not p-cresol
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4-Oxalocrotonate
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strain 345: induced by growth with m-toluate, strain RA1012: induced by growth with p-cresol, but not m-toluate
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4-Oxalocrotonate
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enzyme of the phenol/3,4-dimethylphenol catabolic pathway
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4-Oxalocrotonate
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enzyme of the phenol/3,4-dimethylphenol catabolic pathway
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4-Oxalocrotonate
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enzyme is involved in the meta-cleavage pathway for catechols
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4-Oxalocrotonate
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phenol and m-cresol are inducers
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4-Oxalocrotonate
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enzyme is involved in the meta-cleavage pathway for catechols
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4-Oxalocrotonate
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phenol and m-cresol are inducers
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Mg2+
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required
Mg2+
assay in presence of 5 mM Mg2+
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(2E)-2-fluorohex-2-en-4-ynoic acid
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(2E)-2-fluoropent-2-en-4-ynoic acid
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(2E)-2-fluoropenta-2,4-dienoic acid
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(2E,4E)-2-fluorohexa-2,4-dienedioic acid
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(2E,4E)-2-fluorohexa-2,4-dienoic acid
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(2Z)-2-fluorohex-2-en-4-ynedioic acid
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(2Z)-2-fluoropent-2-en-4-ynoic acid
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(2Z)-2-fluoropenta-2,4-dienoic acid
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(2Z,4E)-2-fluorohexa-2,4-dienoic acid
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CoCl2
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1 mM, 47% remaining activity
FeSO4
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1 mM, 23% remaining activity
iodoacetic acid
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1 mM, 64% remaining activity
K3Fe(CN)6
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1 mM, 36% remaining activity
MnSO4
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1 mM, 9% remaining activity
N-Methylmaleimide
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1 mM, 58% remaining activity
p-chloromercuribenzoic acid
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1 mM, 54% remaining activity
Tiron
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1 mM, 59% remaining activity
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0.0049 - 0.0647
(3E)-2-oxohex-3-enedioate
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2-oxo-3-hexenedioate
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pH 7.3
0.006 - 0.047
4-oxalocrotonate
0.0049
(3E)-2-oxohex-3-enedioate
25°C, pH 8.0
0.0199
(3E)-2-oxohex-3-enedioate
25°C, pH 7.4
0.0222
(3E)-2-oxohex-3-enedioate
25°C, pH 7.0
0.0517
(3E)-2-oxohex-3-enedioate
25°C, pH 6.0
0.0647
(3E)-2-oxohex-3-enedioate
25°C, pH 6.5
0.006
4-oxalocrotonate
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mutant E111Q, in complex with vinylpuruvate hydratase
0.0066
4-oxalocrotonate
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wild-type, in complex with vinylpuruvate hydratase
0.047
4-oxalocrotonate
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mutant E109Q, in complex with vinylpuruvate hydratase
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21.8 - 108.4
(3E)-2-oxohex-3-enedioate
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2-oxo-3-hexenedioate
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0.02 - 68
4-oxalocrotonate
21.8
(3E)-2-oxohex-3-enedioate
25°C, pH 8.0
22.5
(3E)-2-oxohex-3-enedioate
25°C, pH 6.0
98.8
(3E)-2-oxohex-3-enedioate
25°C, pH 7.4
104.2
(3E)-2-oxohex-3-enedioate
25°C, pH 7.0
108.4
(3E)-2-oxohex-3-enedioate
25°C, pH 6.5
0.02
4-oxalocrotonate
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mutant E111Q, in complex with vinylpuruvate hydratase
0.03
4-oxalocrotonate
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mutant E109Q, in complex with vinylpuruvate hydratase
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4-oxalocrotonate
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wild-type, in complex with vinylpuruvate hydratase
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440 - 5000
(3E)-2-oxohex-3-enedioate
440
(3E)-2-oxohex-3-enedioate
25°C, pH 6.0
1700
(3E)-2-oxohex-3-enedioate
25°C, pH 6.5
4500
(3E)-2-oxohex-3-enedioate
25°C, pH 8.0
4700
(3E)-2-oxohex-3-enedioate
25°C, pH 7.0
5000
(3E)-2-oxohex-3-enedioate
25°C, pH 7.4
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0.0068
(2E)-2-fluorohex-2-en-4-ynoic acid
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pH 7.3, 22°C
0.014
(2E)-2-fluoropent-2-en-4-ynoic acid
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pH 7.3, 22°C
0.00011
(2E)-2-fluoropenta-2,4-dienoic acid
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pH 7.3, 22°C
0.045
(2E,4E)-2-fluorohexa-2,4-dienedioic acid
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pH 7.3, 22°C
0.0022
(2E,4E)-2-fluorohexa-2,4-dienoic acid
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pH 7.3, 22°C
0.0003
(2Z)-2-fluorohex-2-en-4-ynedioic acid
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pH 7.3, 22°C
0.05
(2Z)-2-fluoropent-2-en-4-ynoic acid
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pH 7.3, 22°C
0.00034
(2Z)-2-fluoropenta-2,4-dienoic acid
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pH 7.3, 22°C
0.0085
(2Z,4E)-2-fluorohexa-2,4-dienoic acid
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pH 7.3, 22°C
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18
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after 360fold purification
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DSM6285
UniProt
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DSM6285
UniProt
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UniProt
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mt-2
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basonym Alcaligenes eutrophus
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brenda
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brenda
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UniProt
brenda
mt-2
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brenda
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brenda
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brenda
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25000 - 30000
gel filtration
26000
dynamic light scattering
28900
calculated from the deduced amino acid sequences
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additional information
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enzyme forms a complex with vinylpyruvate hydratase, which is only active when stabilized in this complex
monomer
1 * 28400, calculated from sequence
monomer
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1 * 28400, calculated from sequence
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crystal structures for NahK in apo form and bonded with substrate analogues. A lid domain may be implicated in substrate binding
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E109Q
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7fold increase in Km-value, 2270fold decrease in kcat, no influence of mutation to vinylpyruvate hydratase activity
E111Q
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Km-value comparable to wild-type, 3400fold decrease in kcat no influence of mutation to vinylpyruvate hydratase activity
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complex with vinylpyruvate hydratase, homogenetiy
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DE52 cellulose column chromatography and DEAE-Cellulofine A800 column chromatography, DEAE-Toyopearl column chromatography, streptomycin sulfate precipitation, and ammonium sulfate precipitation
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expression and purification of a monomeric, stable and active 4-OD in the absence of vinylpyruvate hydratase
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expression in Escherichia coli
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synthesis
expression and purification of a monomeric, stable and active enzyme in the absence of vinylpyruvate hydratase
synthesis
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expression and purification of a monomeric, stable and active enzyme in the absence of vinylpyruvate hydratase
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Hughes, E.J.L.; Bayly, R.C.; Skurray, R.A.
Evidence for isofunctional enzymes in the degradation of phenol, m- and p-toluate, and p-cresol via catechol meta-cleavage pathways in Alcaligenes eutrophus
J. Bacteriol.
158
79-83
1984
Cupriavidus necator, Cupriavidus necator 345, Cupriavidus necator RA1012
brenda
Kukor, J.J.; Olsen, R.H.
Genetic organization and regulation of a meta cleaveage pathway for catechols produced from catabolism of toluene, benzene, phenol, and cresols by Pseudomonas pickettii PKO1
J. Bacteriol.
173
4587-4594
1991
Ralstonia pickettii, Ralstonia pickettii PKO1
brenda
Shingler, V.; Powlowski, J.; Marklund, U.
Nucleotide sequence and functional analysis of the complete phenol/3,4-dimethylphenol catabolic pathway of Pseudomonas sp. strain CF600
J. Bacteriol.
174
711-724
1992
Pseudomonas sp., Pseudomonas sp. CF 600
brenda
Lian, H.; Whitman, C.P.
Stereochemical and isotopic labelling studies of 4-oxalocrotonate decarboxylase and vinylpyruvate hydratase: analysis and mechanistic implications
J. Am. Chem. Soc.
116
10403-10411
1994
Pseudomonas putida
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brenda
Stanley, T.M.; Johnson, W.H., Jr.; Burks, E.A.; Whitman, C.P.; Hwang, C.C.; Cook, P.F.
Expression and stereochemical and isotope effect studies of active 4-oxalocrotonate decarboxylase
Biochemistry
39
718-726
2000
Pseudomonas putida, Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
brenda
Johnson, W.H., Jr.; Wang, S.C.; Stanley, T.M.; Czerwinski, R.M.; Almrud, J.J.; Poelarends, G.J.; Murzin, A.G.; Whitman, C.P.
4-Oxalocrotonate tautomerase, its homologue YwhB, and active vinylpyruvate hydratase: synthesis and evaluation of 2-fluoro substrate analogues
Biochemistry
43
10490-10501
2004
Pseudomonas putida
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Orii, C.; Takenaka, S.; Murakami, S.; Aoki, K.
Metabolism of 4-amino-3-hydroxybenzoic acid by Bordetella sp. strain 10d: a different modified meta-cleavage pathway for 2-aminophenols
Biosci. Biotechnol. Biochem.
70
2653-2661
2006
Bordetella sp., Bordetella sp. 10d
brenda
Omokoko, B.; Jaentges, U.K.; Zimmermann, M.; Reiss, M.; Hartmeier, W.
Isolation of the phe-operon from G. stearothermophilus comprising the phenol degradative meta-pathway genes and a novel transcriptional regulator
BMC Microbiol.
8
197
2008
Geobacillus stearothermophilus (B0VXM8), Geobacillus stearothermophilus, Geobacillus stearothermophilus DSM 6285 (B0VXM8)
brenda
Guimaraes, S.L.; Coitinho, J.B.; Costa, D.M.; Araujo, S.S.; Whitman, C.P.; Nagem, R.A.
Crystal structures of apo and liganded 4-oxalocrotonate decarboxylase uncover a structural basis for the metal-assisted decarboxylation of a vinylogous beta-keto acid
Biochemistry
55
2632-2645
2016
Pseudomonas putida (Q1XGK3), Pseudomonas putida G7 (Q1XGK3), Pseudomonas putida G7
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