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Information on EC 1.14.13.7 - phenol 2-monooxygenase (NADPH)
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1.14.13.7 phenol 2-monooxygenase (NADPH)IUBMB Comments
A flavoprotein (FAD). The enzyme from the fungus Trichosporon cutaneum has a broad substrate specificity, and has been reported to catalyse the hydroxylation of a variety of substituted phenols, such as fluoro-, chloro-, amino- and methyl-phenols and also dihydroxybenzenes. cf. EC 1.14.14.20, phenol 2-monooxygenase (FADH2).
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Word Map
- 1.14.13.7
- catechols
-
phenol-degrading
- hydroxylases
-
2,3-dioxygenase
- trichosporon
- cutaneum
-
meta-cleavage
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diiron
- cresol
- comamonas
-
2-hydroxymuconic
- testosteroni
-
haldane
-
coke
- radioresistens
-
carboxylate-bridged
-
meta-pathway
-
ortho-cleavage
-
methylococcus
- cis,cis-muconate
-
coking
- environmental protection
- industry
- synthesis
- degradation
The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
Synonyms
phenol hydroxylase, multicomponent phenol hydroxylase, flavin containing monooxygenase, multi-component phenol hydroxylase, phind, dmplno, multicomponent ph, ncgl2588, single-component ph, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
flavin containing monooxygenase
LmPH
Mph
multicomponent PH
multicomponent phenol hydroxylase
oxygenase, phenol 2-mono-
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-
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phenol hydroxylase
phenol o-hydroxylase
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-
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PHH
phhY
PHIND
PHO
PHR
single-component PH
SPH
LmPH
A5YUW2, A5YUW3, A5YUW6, A5YUY2, A5YUY5, A5YUY6, A5YUY7, A5YUZ3, A5YUZ5, A5YUZ6, A5YUZ7, A5YUZ8, A5YUZ9, A5YV00, A5YV01, A5YV02, A5YV03, A5YV04, A5YV05, A5YV06, A5YV08, A5YV10, A5YV11, A5YV12, A5YV13, A5YV14, A5YV15, A5YV16, A5YV18, A5YV19, A5YV20
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phenol hydroxylase
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-
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phenol hydroxylase
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multicomponent enzyme made up of three moieties: a reductase (PHR), and an oxygenase (PHO) and a regulative component
phenol hydroxylase
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multicomponent enzyme made up of three moieties: a reductase (PHR), and an oxygenase (PHO) and a regulative component
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
phenol + NADPH + H+ + O2 = catechol + NADP+ + H2O
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-
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phenol + NADPH + H+ + O2 = catechol + NADP+ + H2O
catalytic mechanism, conformational changes upon binding of the regulatory protein comonent and effects on catalytic activity
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phenol + NADPH + H+ + O2 = catechol + NADP+ + H2O
catalytic mechanism, conformational changes upon binding of the regulatory protein comonent and effects on catalytic activity
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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-
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redox reaction
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reduction
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-
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
phenol,NADPH:oxygen oxidoreductase (2-hydroxylating)
A flavoprotein (FAD). The enzyme from the fungus Trichosporon cutaneum has a broad substrate specificity, and has been reported to catalyse the hydroxylation of a variety of substituted phenols, such as fluoro-, chloro-, amino- and methyl-phenols and also dihydroxybenzenes. cf. EC 1.14.14.20, phenol 2-monooxygenase (FADH2).
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CAS REGISTRY NUMBER
COMMENTARY
37256-84-1
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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
1,3-dihydroxybenzene + NADPH + H+ + O2
? + NADP+ + H2O
-
50.12% activity compared to phenol
-
-
?
2 2-cresol + NADPH + O2
3-methylcatechol + 4-methylcatechol + NADP+ + H2O
-
-
-
-
?
2 2-xylene + 2 NADPH + 2 H+ + 2 O2
2,3-dimethylphenol + 3,4-dimethylphenol + 2 NADP+ + 2 H2O
2 ethynylbenzene + NADPH + 3 O2
2-ethynylphenol + 2-hydroxy-6-oxo-octa-2,4-dien-7-ynoic acid + NADP+ + H2O
2,3,5,6-tetrafluorophenol + O2 + NADPH
3,4,6-trifluoro-2-benzoquinone + NADP+ + F-
-
-
-
?
2-hydroxybenzoic acid + NADPH + H+ + O2
? + NADP+ + H2O
-
15.97% activity compared to phenol
-
-
?
2-naphthol + NADPH + H+ + O2
? + NADP+ + H2O
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9.75% activity compared to phenol
-
-
?
3-aminophenol + NADPH + H+ + O2
3-aminocatechol + NADP+ + H2O
-
-
-
-
?
3-cresol + NADPH + O2
3-methylcatechol + 4-methylcatechol + NADP+ + H2O
-
-
-
-
?
3-hydroxybenzaldehyde + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
-
?
3-hydroxybenzoic acid + NADPH + H+ + O2
? + NADP+ + H2O
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18.53% activity compared to phenol
-
-
?
3-nitrophenol + NADPH + H+ + O2
?
-
about 45% of the activity with phenol
-
-
?
4-bromophenol + NADPH + H+ + O2
4-bromocatechol + NADP+ + H2O
-
-
-
-
?
4-chlorophenol + NADPH + H+ + O2
4-chlorocatechol + NADP+ + H2O
-
-
-
-
?
4-chlorophenol + NADPH + H+ + O2
? + NADP+ + H2O
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28.6% activity compared to phenol
-
-
?
4-cresol + NADPH + O2
4-methylcatechol + NADP+ + H2O
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best substrate
-
-
?
4-fluorophenol + NADH + H+ + O2
1,2-dihydroxy-4-fluorobenzene + NAD+ + H2O
-
-
-
-
?
4-fluorophenol + O2 + NADPH
?
-
-
-
-
?
4-hydroxybenzaldehyde + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
-
?
4-hydroxybenzoic acid + NADPH + H+ + O2
? + NADP+ + H2O
-
14.88% activity compared to phenol
-
-
?
4-hydroxyphenol + NADPH + H+ + O2
?
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about 120% of the activity with phenol
-
-
?
4-methylphenol + NADH + H+ + O2
1,2-dihydroxy-4-methylbenzene + NAD+ + H2O
-
-
-
-
?
4-nitrophenol + NADPH + H+ + O2
4-nitrocatechol + NADP+ + H2O
-
-
-
-
?
4-nitrophenol + NADPH + H+ + O2
?
-
about 50% of the activity with phenol
-
-
?
dibenzofuran + NADPH + H+ + O2
1,2-dihydroxydibenzofuran + NADP+ + H2O
-
-
-
-
?
hydroquinone + NADPH + H+ + O2
? + NADP+ + H2O
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48.25% activity compared to phenol
-
-
?
m-chlorophenol + NADPH + O2
4-chloro-benzene-1,2-diol + NADP+ + H2O
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18% of the activity with phenol
-
-
?
m-cresol + NADPH + H+ + O2
3-methylcatechol + 4-methylcatechol + NADP+
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-
95% 3-methylcatechol, 5% 4-methylcatechol
-
?
o-chlorophenol + NADPH + O2
3-chloro-benzene-1,2-diol + NADP+ + H2O
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20% of the activity with phenol
-
-
?
o-cresol + NADPH + O2
3-methylcatechol + NADP+ + H2O
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37% of the activity with phenol, measured as substrate-dependent oxygen uptake rate by derivatives of Pseudomonas aeruginosa PAO1c carrying the enzyme genes after induction with phenol
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-
?
p-cresol + NADPH + O2
4-methylcatechol + NADP+ + H2O
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114% of the activity with phenol
-
-
?
toluene + NADPH + H+ + O2
o-cresol + m-cresol + p-cresol + NADP+
-
-
48% o-cresol, 11% m-cresol, 41% p-cresol
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?
2 2-xylene + 2 NADPH + 2 H+ + 2 O2
2,3-dimethylphenol + 3,4-dimethylphenol + 2 NADP+ + 2 H2O
-
-
-
-
?
2 2-xylene + 2 NADPH + 2 H+ + 2 O2
2,3-dimethylphenol + 3,4-dimethylphenol + 2 NADP+ + 2 H2O
-
-
-
-
?
2 ethynylbenzene + NADPH + 3 O2
2-ethynylphenol + 2-hydroxy-6-oxo-octa-2,4-dien-7-ynoic acid + NADP+ + H2O
-
-
product identification by GC-MS
-
?
2 ethynylbenzene + NADPH + 3 O2
2-ethynylphenol + 2-hydroxy-6-oxo-octa-2,4-dien-7-ynoic acid + NADP+ + H2O
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substrate only for phenol-grown cells
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-
?
2 ethynylbenzene + NADPH + 3 O2
2-ethynylphenol + 2-hydroxy-6-oxo-octa-2,4-dien-7-ynoic acid + NADP+ + H2O
-
-
product identification by GC-MS
-
?
2 ethynylbenzene + NADPH + 3 O2
2-ethynylphenol + 2-hydroxy-6-oxo-octa-2,4-dien-7-ynoic acid + NADP+ + H2O
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substrate only for phenol-grown cells
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-
?
2,4-dichlorophenol + NADPH + H+ + O2
2,4-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + H+ + O2
2,4-dichlorocatechol + NADP+ + H2O
Auxenochlorella pyrenoidosa NCIM 2738
-
-
-
-
?
2-aminophenol + NADPH + H+ + O2
2-aminocatechol + NADP+ + H2O
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-
-
-
?
2-aminophenol + NADPH + H+ + O2
2-aminocatechol + NADP+ + H2O
Auxenochlorella pyrenoidosa NCIM 2738
-
-
-
-
?
2-chlorophenol + NADPH + H+ + O2
2-chlorocatechol + NADP+ + H2O
-
-
-
-
?
2-chlorophenol + NADPH + H+ + O2
2-chlorocatechol + NADP+ + H2O
Auxenochlorella pyrenoidosa NCIM 2738
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-
-
-
?
2-ethylphenol + NADPH + O2
3-ethyl-benzene-1,2-diol + NADP+ + H2O
-
18% of the activity with phenol
-
-
?
2-ethylphenol + NADPH + O2
3-ethyl-benzene-1,2-diol + NADP+ + H2O
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18% of the activity with phenol
-
-
?
2-hydroxyphenol + NADPH + H+ + O2
?
-
about 70% of the activity with phenol
-
-
?
2-hydroxyphenol + NADPH + H+ + O2
?
-
about 70% of the activity with phenol
-
-
?
2-nitrophenol + NADPH + H+ + O2
?
-
about 80% of the activity with phenol
-
-
?
2-nitrophenol + NADPH + H+ + O2
?
-
about 80% of the activity with phenol
-
-
?
3 toluene + 3 NADPH + 3 H+ + 3 O2
2-cresol + 3-cresol + 4-cresol + 3 NADP+ + 3 H2O
-
-
-
-
?
3 toluene + 3 NADPH + 3 H+ + 3 O2
2-cresol + 3-cresol + 4-cresol + 3 NADP+ + 3 H2O
-
-
-
-
?
3 toluene + 3 NADPH + 3 H+ + 3 O2
2-cresol + 3-cresol + 4-cresol + 3 NADP+ + 3 H2O
-
-
-
-
?
3 toluene + 3 NADPH + 3 H+ + 3 O2
2-cresol + 3-cresol + 4-cresol + 3 NADP+ + 3 H2O
-
regioselectivity, overview
-
-
?
3 toluene + 3 NADPH + 3 H+ + 3 O2
2-cresol + 3-cresol + 4-cresol + 3 NADP+ + 3 H2O
-
regioselectivity, overview
-
-
?
3 toluene + 3 NADPH + 3 H+ + 3 O2
2-cresol + 3-cresol + 4-cresol + 3 NADP+ + 3 H2O
-
-
-
-
?
3,4-dimethylphenol + NADH + H+ + O2
1,2-dihydroxy-3,4-dimethylbenzene + NAD+ + H2O
-
85% of the activity with phenol
-
-
?
3,4-dimethylphenol + NADH + H+ + O2
1,2-dihydroxy-3,4-dimethylbenzene + NAD+ + H2O
-
85% of the activity with phenol
-
-
?
3,4-dimethylphenol + NADPH + O2
?
-
72% of the activity with phenol
-
-
?
3,4-dimethylphenol + NADPH + O2
?
-
72% of the activity with phenol
-
-
?
3-chlorophenol + NADH + H+ + O2
4-chlorocatechol + NAD+ + H2O
-
15% of the activity with phenol
-
-
?
3-chlorophenol + NADH + H+ + O2
4-chlorocatechol + NAD+ + H2O
-
15% of the activity with phenol
-
-
?