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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
2,3,4-trifluorophenol + O2 + NADPH
?
-
-
-
?
2,3,5,6-tetrafluorophenol + O2 + NADPH
3,4,6-trifluoro-2-benzoquinone + NADP+ + F-
-
-
-
?
2,3,5,6-tetrafluorophenol + O2 + NADPH
?
-
-
-
?
2,3,5-trifluorophenol + O2 + NADPH
?
-
-
-
?
2,3,6-trifluorophenol + O2 + NADPH
?
-
-
-
?
2,3-difluorophenol + O2 + NADPH
?
-
-
-
?
2,4-difluorophenol + O2 + NADPH
?
-
-
-
?
2,5-difluorophenol + O2 + NADPH
?
-
-
-
?
2,6-difluorophenol + O2 + NADPH
?
-
-
-
?
2-amino-3-methylphenol + O2 + NADPH
?
-
-
-
?
2-aminophenol + O2 + NADPH
?
2-chlorophenol + O2 + NADPH
?
2-ethylphenol + NADPH + O2
3-ethyl-benzene-1,2-diol + NADP+ + H2O
2-fluorophenol + O2 + NADPH
?
-
-
-
?
2-hydroxybenzoic acid + NADPH + H+ + O2
? + NADP+ + H2O
-
15.97% activity compared to phenol
-
?
2-hydroxyphenol + NADPH + H+ + O2
?
2-methyl-phenol + O2 + NADPH
?
2-methylindole + NADPH + O2
?
-
-
-
?
2-naphthol + NADPH + H+ + O2
? + NADP+ + H2O
-
9.75% activity compared to phenol
-
?
2-nitrophenol + NADPH + H+ + O2
?
3 toluene + 3 NADPH + 3 H+ + 3 O2
2-cresol + 3-cresol + 4-cresol + 3 NADP+ + 3 H2O
3,4,5-trifluorophenol + O2 + NADPH
?
-
-
-
?
3,4-difluorophenol + O2 + NADPH
?
-
-
-
?
3,4-dimethylphenol + NADH + H+ + O2
1,2-dihydroxy-3,4-dimethylbenzene + NAD+ + H2O
3,4-dimethylphenol + NADPH + O2
?
3,5-difluorophenol + O2 + NADPH
?
-
-
-
?
3-aminophenol + O2 + NADPH
?
3-chloro-4-fluorophenol + O2 + NADPH
?
-
-
-
?
3-chlorophenol + NADH + H+ + O2
4-chlorocatechol + NAD+ + H2O
3-chlorophenol + O2 + NADPH
?
3-cresol + NADPH + H+ + O2
3-methylcatechol + NADP+ + H2O
3-cresol + NADPH + O2
3-methylcatechol + 4-methylcatechol + NADP+ + H2O
-
-
-
?
3-cyanoindole + NADPH + O2
?
-
substrate only of strain KL28
-
?
3-ethylphenol + NADH + H+ + O2
4-ethylcatechol + NAD+ + H2O
3-fluorophenol + O2 + NADPH
?
3-hydroxybenzoic acid + NADPH + H+ + O2
? + NADP+ + H2O
-
18.53% activity compared to phenol
-
?
3-hydroxyphenol + NADPH + H+ + O2
?
3-hydroxyphenol + O2 + NADPH
?
-
-
-
?
3-methylphenol + O2 + NADPH
?
3-nitrophenol + NADPH + H+ + O2
?
-
about 45% of the activity with phenol
-
?
4-aminophenol + O2 + NADPH
?
4-chloro-3-fluorophenol + O2 + NADPH
?
-
-
-
?
4-chlorocatechol + O2 + NADPH
?
-
-
-
?
4-chlorophenol + NADH + H+ + O2
1,2-dihydroxy-4-methylbenzene + NAD+ + H2O
4-chlorophenol + NADH + H+ + O2
4-chlorocatechol + NAD+ + H2O
-
27% of the activity with phenol
-
?
4-chlorophenol + NADH + H+ + O2
4-chlorochatechol + NAD+ + H2O
-
-
?
4-chlorophenol + NADPH + H+ + O2
? + NADP+ + H2O
-
28.6% activity compared to phenol
-
?
4-chlorophenol + O2 + NADPH
?
4-cresol + NADPH + H+ + O2
4-methylcatechol + NADP+ + H2O
4-cresol + NADPH + O2
4-methylcatechol + NADP+ + H2O
-
best substrate
-
?
4-ethylphenol + NADH + H+ + O2
4-ethylcatechol + NAD+ + H2O
4-fluorophenol + NADH + H+ + O2
1,2-dihydroxy-4-fluorobenzene + NAD+ + H2O
-
-
-
?
4-fluorophenol + O2 + NADPH
?
-
-
-
?
4-hydroxybenzoic acid + NADPH + H+ + O2
? + NADP+ + H2O
-
14.88% activity compared to phenol
-
?
4-hydroxyindole + NADPH + O2
?
-
-
-
?
4-hydroxyphenol + NADPH + H+ + O2
?
-
about 120% of the activity with phenol
-
?
4-hydroxyphenol + O2 + NADPH
?
-
-
-
?
4-methoxyindole + NADPH + O2
?
-
substrate only of strain KL28
-
?
4-methyl-phenol + O2 + NADPH
?
4-methylindole + NADPH + O2
?
-
substrate only of strain KL28
-
?
4-methylphenol + NADH + H+ + O2
1,2-dihydroxy-4-methylbenzene + NAD+ + H2O
-
-
-
?
4-nitrophenol + NADPH + H+ + O2
?
-
about 50% of the activity with phenol
-
?
4-propylphenol + NADH + H+ + O2
4-propylcatechol + NAD+ + H2O
5-aminoindole + NADPH + O2
?
-
-
-
?
5-fluoroindole + NADPH + O2
?
-
substrate only of strain KL33
-
?
5-hydroxyindole + NADPH + O2
?
-
-
-
?
5-methoxyindole + NADPH + O2
?
-
-
-
?
5-methylindole + NADPH + O2
?
-
substrate only of strain KL33
-
?
6-chloroindole + NADPH + O2
?
-
substrate only of strain KL33
-
?
6-methoxyindole + NADPH + O2
?
-
-
-
?
6-methylindole + NADPH + O2
?
-
substrate only of strain KL33
-
?
7-chloroindole + NADPH + O2
?
-
substrate only of strain KL33
-
?
7-methylindole + NADPH + O2
?
-
-
-
?
benzene + NADPH + H+ + O2
phenol + NADP+
-
-
-
?
benzene + NADPH + O2
?
-
26% of the activity with phenol
-
?
benzene + NADPH + O2 + H+
phenol + NADP+ + H2O
dibenzofuran + NADPH + H+ + O2
1,2-dihydrobenzofuran + NADP+ + H2O
-
-
-
?
hydroquinone + NADPH + H+ + O2
? + NADP+ + H2O
-
48.25% activity compared to phenol
-
?
indole + NADPH + O2
7-hydroxyindole + NADP+ + H2O
-
-
-
?
m-chlorophenol + NADPH + O2
4-chloro-benzene-1,2-diol + NADP+ + H2O
-
18% of the activity with phenol
-
?
m-cresol + NADH + H+ + O2
4-methylcatechol + NAD+ + H2O
m-cresol + NADPH + H+ + O2
3-methylcatechol + 4-methylcatechol + NADP+
-
-
95% 3-methylcatechol, 5% 4-methylcatechol
?
m-cresol + NADPH + O2
?
-
114% of the activity with phenol
-
?
metol + O2 + NADPH
?
-
-
-
?
o-chlorophenol + NADPH + O2
3-chloro-benzene-1,2-diol + NADP+ + H2O
-
20% of the activity with phenol
-
?
o-cresol + NADH + H+ + O2
3-methylcatechol + NAD+ + H2O
o-cresol + NADPH + O2
3-methylcatechol + NADP+ + H2O
-
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
-
?
orcinol + NADPH + O2
?
-
46% of the activity with phenol
-
?
oxindole + NADPH + O2
?
-
-
-
?
p-chlorophenol + NADPH + O2
?
-
84% of the activity with phenol
-
?
p-cresol + NADH + H+ + O2
4-methylcatechol + NAD+ + H2O
p-cresol + NADPH + O2
4-methylcatechol + NADP+ + H2O
-
114% of the activity with phenol
-
?
pentafluorophenol + O2 + NADPH
?
-
-
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
phenol + NADPH + H+ + O2
catechol + NADP+
-
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
phenol + NADPH + O2
?
-
enzyme of phenol degradation pathway
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
phloroglucinol + O2 + NADPH
?
quinol + NADPH + O2
?
-
63% of the activity with phenol
-
?
quinol + O2 + NADPH
1,2,4-trihydroxybenzene + NADP+ + H2O
resorcinol + NADPH + O2
?
thiophenol + O2 + NADPH
?
-
-
-
?
toluene + NADPH + H+ + O2
o-cresol + m-cresol + p-cresol + NADP+
-
-
48% o-cresol, 11% m-cresol, 41% p-cresol
?
toluene + NADPH + O2
?
-
28% of the activity with phenol
-
?
various phenolic substrates + NADPH + H+ + O2
?
-
-
-
?
additional information
?
-
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
-
substrate only for phenol-grown cells
-
?
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
-
substrate only for phenol-grown cells
-
?
2-aminophenol + O2 + NADPH

?
-
-
-
?
2-aminophenol + O2 + NADPH
?
-
-
-
?
2-aminophenol + O2 + NADPH
?
-
-
-
?
2-chlorophenol + O2 + NADPH

?
-
-
-
?
2-chlorophenol + O2 + NADPH
?
-
-
-
?
2-chlorophenol + O2 + NADPH
?
-
-
-
?
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
-
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-methyl-phenol + O2 + NADPH

?
-
i.e. o-cresol
-
?
2-methyl-phenol + O2 + NADPH
?
-
i.e. o-cresol
-
?
2-methyl-phenol + O2 + NADPH
?
-
-
-
?
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-aminophenol + O2 + NADPH

?
-
-
-
?
3-aminophenol + O2 + NADPH
?
-
-
-
?
3-aminophenol + O2 + NADPH
?
-
-
-
?
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
-
?
3-chlorophenol + O2 + NADPH

?
-
-
-
?
3-chlorophenol + O2 + NADPH
?
-
-
-
?
3-chlorophenol + O2 + NADPH
?
-
-
-
?
3-cresol + NADPH + H+ + O2

3-methylcatechol + NADP+ + H2O
-
-
-
?
3-cresol + NADPH + H+ + O2
3-methylcatechol + NADP+ + H2O
-
-
-
?
3-ethylphenol + NADH + H+ + O2

4-ethylcatechol + NAD+ + H2O
-
-
-
?
3-ethylphenol + NADH + H+ + O2
4-ethylcatechol + NAD+ + H2O
-
-
-
?
3-fluorophenol + O2 + NADPH

?
-
-
-
?
3-fluorophenol + O2 + NADPH
?
-
below pH 6.5 3-fluorophenol is preferentially hydroxylated at the C6 ortho position, at increasing pH the C2 ortho-hydroxylation becomes more predominant
-
?
3-hydroxyphenol + NADPH + H+ + O2

?
-
about 60% of the activity with phenol
-
?
3-hydroxyphenol + NADPH + H+ + O2
?
-
about 60% of the activity with phenol
-
?
3-methylphenol + O2 + NADPH

?
-
i.e. m-cresol
-
?
3-methylphenol + O2 + NADPH
?
-
i.e. m-cresol
-
?
3-methylphenol + O2 + NADPH
?
-
-
-
?
3-methylphenol + O2 + NADPH
?
-
i.e. m-cresol
-
?
4-aminophenol + O2 + NADPH

?
-
-
-
?
4-aminophenol + O2 + NADPH
?
-
-
-
?
4-aminophenol + O2 + NADPH
?
-
-
-
?
4-chlorophenol + NADH + H+ + O2

1,2-dihydroxy-4-methylbenzene + NAD+ + H2O
-
-
-
?
4-chlorophenol + NADH + H+ + O2
1,2-dihydroxy-4-methylbenzene + NAD+ + H2O
-
-
-
?
4-chlorophenol + O2 + NADPH

?
-
-
-
?
4-chlorophenol + O2 + NADPH
?
-
-
-
?
4-chlorophenol + O2 + NADPH
?
-
-
-
?
4-cresol + NADPH + H+ + O2

4-methylcatechol + NADP+ + H2O
-
-
-
?
4-cresol + NADPH + H+ + O2
4-methylcatechol + NADP+ + H2O
-
-
-
?
4-ethylphenol + NADH + H+ + O2

4-ethylcatechol + NAD+ + H2O
-
-
-
?
4-ethylphenol + NADH + H+ + O2
4-ethylcatechol + NAD+ + H2O
-
-
-
?
4-methyl-phenol + O2 + NADPH

?
-
-
-
?
4-methyl-phenol + O2 + NADPH
?
-
i.e. p-cresol
-
?
4-methyl-phenol + O2 + NADPH
?
-
-
-
?
4-propylphenol + NADH + H+ + O2

4-propylcatechol + NAD+ + H2O
-
low activity
-
?
4-propylphenol + NADH + H+ + O2
4-propylcatechol + NAD+ + H2O
-
low activity
-
?
benzene + NADPH + O2 + H+

phenol + NADP+ + H2O
-
-
-
?
benzene + NADPH + O2 + H+
phenol + NADP+ + H2O
-
-
-
?
benzene + NADPH + O2 + H+
phenol + NADP+ + H2O
-
-
-
?
benzene + NADPH + O2 + H+
phenol + NADP+ + H2O
-
-
-
?
catechol + O2 + NADPH

?
-
-
-
?
catechol + O2 + NADPH
?
-
-
-
?
m-cresol + NADH + H+ + O2

4-methylcatechol + NAD+ + H2O
-
60% of the activity with phenol
-
?
m-cresol + NADH + H+ + O2
4-methylcatechol + NAD+ + H2O
-
-
-
?
m-cresol + NADH + H+ + O2
4-methylcatechol + NAD+ + H2O
-
-
-
?
o-cresol + NADH + H+ + O2

3-methylcatechol + NAD+ + H2O
-
60% of the activity with phenol
-
?
o-cresol + NADH + H+ + O2
3-methylcatechol + NAD+ + H2O
-
low activity
-
?
orcinol + O2 + NADPH

?
-
-
-
?
orcinol + O2 + NADPH
?
-
weak
-
?
p-cresol + NADH + H+ + O2

4-methylcatechol + NAD+ + H2O
-
60% of the activity with phenol
-
?
p-cresol + NADH + H+ + O2
4-methylcatechol + NAD+ + H2O
-
-
-
?
phenol + NAD(P)H + H+ + O2

catechol + NAD(P)+ + H2O
-
-
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
can tolerate the phenol concentration up to 6 mM, degrades phenol through catechol ortho fission pathway
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
can tolerate the phenol concentration up to 6 mM, degrades phenol through catechol ortho fission pathway
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
-
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
-
-
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
-
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
can tolerate the phenol concentration up to 1 mM, harbors the both ortho and meta fission pathways simultaneously
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
can tolerate the phenol concentration up to 6 mM, harbors the both ortho and meta fission pathways simultaneously
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
can tolerate the phenol concentration up to 6 mM, degrades phenol through catechol ortho fission pathway
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
can tolerate the phenol concentration up to 6 mM, degrades phenol through catechol ortho fission pathway
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
-
-
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
-
-
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
-
-
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
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 phenol degradation in the activated sludge depends on the combined activity of a number of redundant species
-
?
phenol + NADH + H+ + O2

catechol + NAD+ + H2O
-
-
-
?
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
-
-
-
?
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
-
-
-
?
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
-
activity is reduced by 84% when NADPH is replaced by NADH
-
?
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
-
-
-
?
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
-
-
-
?
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
-
-
-
?
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
-
-
-
?
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
-
-
-
?
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
-
-
-
?
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
-
coupling between phenol hydroxylase and toluene/o-xylene monooxygenase optimizes the use of nonhydroxylated aromatic molecules by the draining effect of phenol hydroxylase on the products of oxidation catalyzed by toluene/o-xylene monooxygenase, thus avoiding phenol accumulation
-
?
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
-
-
-
?
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
-
coupling between phenol hydroxylase and toluene/o-xylene monooxygenase optimizes the use of nonhydroxylated aromatic molecules by the draining effect of phenol hydroxylase on the products of oxidation catalyzed by toluene/o-xylene monooxygenase, thus avoiding phenol accumulation
-
?
phenol + NADPH + H+ + O2

catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
100% activity
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
the enzyme catalyzes the conversion of phenols to their 2-diol derivatives
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
monitoring the production of catechol in a continuous coupled assay with recombinant catechol 2,3-dioxygenase from Pseudomonas sp. OX1
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
monitoring the production of catechol in a continuous coupled assay with recombinant catechol 2,3-dioxygenase from Pseudomonas sp. OX1
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2

catechol + NADP+ + H2O
-
cytochrome c, 2,6-dichlorophenolindophenol, potassium ferricyanide and nitro blue tetrazolium can act as electron acceptors in vitro
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
high phenol degradation activity in vivo in strain TL3, catabolic pathway overview
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
high phenol degradation activity in vivo in strain TL3, catabolic pathway overview
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
initial step in phenol-degrading pathway
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
initial step in phenol-degrading pathway
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
reaction mechanism
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
?
phenol + O2

?
assay at 28°C, pH 6.8-7.0, concentration of phenol diversify from 25 mg/l to 800 mg/l
-
?
phenol + O2
?
utilize phenol as sole carbon and energy source, concentration of phenol diversify from 25 mg/l to 1000 mg/l, assay at 28°C, pH 6.8-7.0
-
?
phenol + O2
?
utilize phenol as sole carbon and energy source, concentration of phenol diversify from 25 mg/l to 1000 mg/l, assay at 28°C, pH 6.8-7.0
-
?
phenol + O2
?
-
assay at 28°C, pH 6.8-7.0, concentration of phenol diversify from 25 mg/l to 800 mg/l
-
?
phloroglucinol + O2 + NADPH

?
-
-
-
?
phloroglucinol + O2 + NADPH
?
-
-
-
?
quinol + O2 + NADPH

1,2,4-trihydroxybenzene + NADP+ + H2O
-
-
-
?
quinol + O2 + NADPH
1,2,4-trihydroxybenzene + NADP+ + H2O
-
-
-
?
resorcinol + NADPH + O2

?
-
-
-
?
resorcinol + NADPH + O2
?
-
-
-
?
resorcinol + NADPH + O2
?
-
27% of the activity with phenol
-
?
resorcinol + NADPH + O2
?
-
27% of the activity with phenol
-
?
resorcinol + NADPH + O2
?
-
-
-
?
resorcinol + NADPH + O2
?
-
reaction mechanism
-
?
additional information

?
-
-
no PHO activity with p-hydroxybenzoic acid, m-hydroxybenzoic acid, 2,3-dinitrophenol, 3,4-dichlorophenol, 2,4,5-trichlorophenol, 2,2'-dihydroxybiphenyl and L-Tyr
-
?
additional information
?
-
-
no PHO activity with p-hydroxybenzoic acid, m-hydroxybenzoic acid, 2,3-dinitrophenol, 3,4-dichlorophenol, 2,4,5-trichlorophenol, 2,2'-dihydroxybiphenyl and L-Tyr
-
?
additional information
?
-
-
the enzyme has broad substrate specificity against isomeric diphenols, isomeric methylphenols, halogen-substituted phenols, amino-substituted phenols, nitrophenols, hydroxybenzaldehyde and hydroxylbenzoic acid
-
?
additional information
?
-
-
not: p-hydroxyphenylacetic acid
-
?
additional information
?
-
-
not: 2,4-, 2,5- and 2,6-dimethylphenols
-
?
additional information
?
-
-
not: p-hydroxybenzoic acid
-
?
additional information
?
-
-
not: salicylic acid
-
?
additional information
?
-
-
broad specificity
-
?
additional information
?
-
-
not: salicylic acid
-
?
additional information
?
-
-
broad specificity, reaction results in the formation of the corresponding o-diols
-
?
additional information
?
-
-
overview of possible reaction products of fluorinated phenols
-
?
additional information
?
-
-
first enzyme of phenol biodegradation
-
?
additional information
?
-
-
the enzyme hydroxylates phenol and several different toxic phenol derivatives, e.g. cresols, nitrophenols and hydroxyphenols, substrate specificity, overview
-
?
additional information
?
-
-
the enzyme hydroxylates phenol and several different toxic phenol derivatives, e.g. cresols, nitrophenols and hydroxyphenols, substrate specificity, overview
-
?
additional information
?
-
-
phenol degradation pathway, overview
-
?
additional information
?
-
-
the enzyme is a hydrocarbon-oxidizing multicomponent monooxygenase, important for activity is formation of a complex between the hydroxylase and a regulatory protein component
-
?
additional information
?
-
-
the enzyme is a multicomponent phenol hydroxylase, production of dyes from indole derivatives by recombinant enzymes expressed in Escherichia coli, substrate specificities of the enzyme from strain KL28 and KL33, the products formed by the enzyme from the two strain are different, detailed overview
-
?
additional information
?
-
-
only complete enzyme systems containing all three or four protein components are capable of oxidizing phenol. The electron-transfer components exert regulatory effects on substrate oxidation processes taking place at the hydroxylase actives sites, most likely through allostery. The regulatory proteins facilitate the electron-transfer step in the hydrocarbon oxidation cycle in the absence of phenol. Under these conditions, electron consumption is coupled to H2O2 formation in a hydroxylase-dependent manner
-
?
additional information
?
-
-
only complete enzyme systems containing all three or four protein components are capable of oxidizing phenol. The electron-transfer components exert regulatory effects on substrate oxidation processes taking place at the hydroxylase actives sites, most likely through allostery. The regulatory proteins facilitate the electron-transfer step in the hydrocarbon oxidation cycle in the absence of phenol. Under these conditions, electron consumption is coupled to H2O2 formation in a hydroxylase-dependent manner
-
?
additional information
?
-
-
the enzyme is a hydrocarbon-oxidizing multicomponent monooxygenase, important for activity is formation of a complex between the hydroxylase and a regulatory protein component
-
?
additional information
?
-
-
the enzyme hydroxylates benzenes to catechols via the intermediate production of phenols
-
?
additional information
?
-
-
the enzyme hydroxylates benzenes to catechols via the intermediate production of phenols
-
?
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Krug, M.; Straube, G.
Degradation of phenolic compounds by the yeast Candida tropicalis HP 15. II. Some properties of the first two enzymes of the degradation pathway
J. Basic Microbiol.
26
271-281
1986
Candida tropicalis
brenda
Neujahr, H.Y.; Gaal, A.
Phenol hydroxylase from yeast. Purification and properties of the enzyme from Trichosporon cutaneum
Eur. J. Biochem.
35
386-400
1973
Cutaneotrichosporon cutaneum
brenda
Nakagawa, H.; Takeda, Y.
Phenol hydroxylase
Biochim. Biophys. Acta
62
423-426
1962
Brevibacterium fuscum
brenda
Neujahr, H.Y.; Gaal, A.
Phenol hydroxylase from yeast. Sulfhydryl groups in phenol hydroxylase from Trichosporon cutaneum
Eur. J. Biochem.
58
351-357
1975
Cutaneotrichosporon cutaneum
brenda
Kjellen, K.G.; Neujahr, H.Y.
Immobilization of phenol hydroxylase
Biotechnol. Bioeng.
21
715-719
1979
Cutaneotrichosporon cutaneum
brenda
Detmer, K.; Massey, V.
Effect of monovalent anions on the mechanism of phenol hydroxylase
J. Biol. Chem.
259
11265-11272
1984
Cutaneotrichosporon cutaneum
brenda
Detmer, K.; Massey, V.
Effect of substrate and pH on the oxidative half-reaction of phenol hydroxylase
J. Biol. Chem.
260
5998-6005
1985
Cutaneotrichosporon cutaneum
brenda
Neujahr, H.Y.; Kjellen, K.G.
Phenol hydroxylase from yeast. Reaction with phenol derivatives
J. Biol. Chem.
253
8835-8841
1978
Cutaneotrichosporon cutaneum
brenda
Neujahr, H.Y.
Effect of anions, chaotropes, and phenol on the attachment of flavin adenine dinucleotide to phenol hydroxylase
Biochemistry
22
580-584
1983
Cutaneotrichosporon cutaneum
brenda
Neujahr, H.Y.; Kjellen, K.G.
Phenol hydroxylase from yeast: a lysyl residue essential for binding of reduced nicotinamide adenine dinucleotide phosphate
Biochemistry
19
4967-4972
1980
Cutaneotrichosporon cutaneum
brenda
Selitz, T.; Neujahr, H.Y.
Phenol hydroxylase from yeast. A model for phenol binding and an improved purification procedure
Eur. J. Biochem.
170
343-349
1987
Cutaneotrichosporon cutaneum
brenda
Mörtberg, M.; Neujahr, H.Y.
In situ and in vitro kinetics of phenol hydroxylase
Biochem. Biophys. Res. Commun.
146
41-46
1987
Cutaneotrichosporon cutaneum
brenda
Cadieux, E.; Vrajmasu, V.; Achim, C.; Powlowski, J.; Muenck, E.
Biochemical, Mossbauer, and EPR studies of the diiron cluster of phenol hydroxylase from Pseudomonas sp. strain CF 600
Biochemistry
41
10680-10691
2002
Pseudomonas sp., Pseudomonas sp. CF 600
brenda
Enroth, C.; Neujahr, H.; Schneider, G.; Lindqvist, Y.
The crystal structure of phenol hydroxylase in complex with FAD and phenol provides evidence for a concerted conformational change in the enzyme and its cofactor during catalysis
Structure
6
605-617
1998
Cutaneotrichosporon cutaneum
brenda
Hino, S.; Watanabe, K.; Takahashi, N.
Phenol hydroxylase cloned from Ralstonia eutropha strain E2 exhibits novel kinetic properties
Microbiology
144
1765-1772
1998
Cupriavidus necator, Cupriavidus necator E2
-
brenda
Kaelin, M.; Neujahr, H.Y.; Weissmahr, R.N.; Sejlitz, T.; Joehl, R.; Fiechter, A.; Reiser, J.
Phenol hydroxylase from Trichosporon cutaneum: gene cloning, sequence analysis, and functional expression in Escherichia coli
J. Bacteriol.
174
7112-7120
1992
Cutaneotrichosporon cutaneum
brenda
Maeda-Yorita, K.; Massey, V.
On the reaction mechanism of phenol hydroxylase. New information obtained by correlation of fluorescence and absorbance stopped flow studies
J. Biol. Chem.
268
4134-4144
1993
Cutaneotrichosporon cutaneum
brenda
Peelen, S.; Rietjens, I.M.C.M.; Boersma, M.G.; Vervoort, J.
Conversion of phenol derivatives to hydroxylated products by phenol hydroxylase from Trichosporon cutaneum. A comparison of regioselectivity and rate of conversion with calculated molecular orbital substrate characteristics
Eur. J. Biochem.
227
284-291
1995
Cutaneotrichosporon cutaneum
brenda
Peelen, S.; Rietjens, I.M.C.M.; van Berkel, W.J.H.; van Workum, W.A.T.; Vervoort, J.
Fluorine-19 NMR study on the pH-dependent regioselectivity and rate of the ortho-hydroxylation of 3-fluorophenol by phenol hydroxylase from Trichosporon cutaneum. Implications for the reaction mechanism
Eur. J. Biochem.
218
345-353
1993
Cutaneotrichosporon cutaneum
brenda
Pessione, E.; Divari, S.; Griva, E.; Cavaletto, M.; Rossi, G.L.; Gilardi, G.; Giunta, C.
Phenol hydroxylase from Acinetobacter radioresistens is a multicomponent enzyme. Purification and characterization of the reductase moiety
Eur. J. Biochem.
265
549-555
1999
Acinetobacter radioresistens
brenda
Waters, S.; Neujahr, H.Y.
A fermentor culture for production of recombinant phenol hydroxylase
Protein Expr. Purif.
5
534-540
1994
Cutaneotrichosporon cutaneum
brenda
Waters, S.; Neujahr, H.Y.
Sources and nature of heterogeneity in recombinant phenol hydroxylase derived from the basidiomycetous soil yeast Trichosporon cutaneum
Biotechnol. Appl. Biochem.
25
235-242
1997
Cutaneotrichosporon cutaneum
-
brenda
Xu, D.; Ballou, D.P.; Massey, V.
Studies of the mechanism of phenol hydroxylase: mutants Tyr289Phe, Asp54Asn, and Arg281Met
Biochemistry
40
12369-12378
2001
Cutaneotrichosporon cutaneum
brenda
Xu, D.; Enroth, C.; Lindqvist, Y.; Ballou, D.P.; Massey, V.
Studies of the mechanism of phenol hydroxylase: Effect of mutation of proline 364 to serine
Biochemistry
41
13627-13636
2002
Cutaneotrichosporon cutaneum
brenda
Enroth, C.
High-resolution structure of phenol hydroxylase and correction of sequence errors
Acta Crystallogr. Sect. D
59
1597-1602
2003
Cutaneotrichosporon cutaneum
brenda
Cafaro, V.; Izzo, V.; Scognamiglio, R.; Notomista, E.; Capasso, P.; Casbarra, A.; Pucci, P.; Di Donato, A.
Phenol hydroxylase and toluene/o-xylene monooxygenase from Pseudomonas stutzeri OX1: interplay between two enzymes
Appl. Environ. Microbiol.
70
2211-2219
2004
Pseudomonas stutzeri, Pseudomonas stutzeri OX1
brenda
Alexievaa, Z.; Gerginova, M.; Zlateva, P.; Peneva, N.
Comparison of growth kinetics and phenol metabolizing enzymes of Trichosporon cutaneum R57 and mutants with modified degradation abilities
Enzyme Microb. Technol.
34
242-247
2004
Cutaneotrichosporon cutaneum
-
brenda
Griva, E.; Pessione, E.; Divari, S.; Valetti, F.; Cavaletto, M.; Rossi, G.L.; Giunta, C.
Phenol hydroxylase from Acinetobacter radioresistens S13. Isolation and characterization of the regulatory component
Eur. J. Biochem.
270
1434-1440
2003
Acinetobacter radioresistens, Acinetobacter radioresistens S13
brenda
Divari, S.; Valetti, F.; Caposio, P.; Pessione, E.; Cavaletto, M.; Griva, E.; Gribaudo, G.; Gilardi, G.; Giunta, C.
The oxygenase component of phenol hydroxylase from Acinetobacter radioresistens S13
Eur. J. Biochem.
270
2244-2253
2003
Acinetobacter radioresistens, Acinetobacter radioresistens S13
brenda
Stiborova, M.; Sucha, V.; Miksanova, M.; Paca, J.Jr.; Paca, J.
Hydroxylation of phenol to catechol by Candida tropicalis: involvement of cytochrome P450
Gen. Physiol. Biophys.
22
167-179
2003
Candida tropicalis
brenda
Jeong, J.J.; Kim, J.H.; Kim, C.K.; Hwang, I.; Lee, K.
3- and 4-alkylphenol degradation pathway in Pseudomonas sp. strain KL28: genetic organization of the lap gene cluster and substrate specificities of phenol hydroxylase and catechol 2,3-dioxygenase
Microbiology
149
3265-3277
2003
Pseudomonas sp., Pseudomonas sp. KL28
brenda
Ahuatzi-Chacon, D.; Ordorica-Morales, G.; Ruiz-Ordaz, N.; Cristiani-Urbina, E.; Juarez-Ramirez, C.; Galindez-Mayer, J.
Kinetic study of phenol hydroxylase and catechol 1,2-dioxygenase dioxygenase biosynthesis by Candida tropicalis cells grown on different phenolic substrates.
World J. Microbiol. Biotechnol.
20
695-702
2004
Candida tropicalis
brenda
Teramoto, M.; Futamata, H.; Harayama, S.; Watanabe, K.
Characterization of a high-affinity phenol hydroxylase from Comamonas testosteroni R5 by gene cloning, and expression in Pseudomonas aeruginosa PAO1c
Mol. Gen. Genet.
262
552-558
1999
Comamonas testosteroni, Comamonas testosteroni R5
brenda
Cafaro, V.; Notomista, E.; Capasso, P.; Di Donato, A.
Regiospecificity of two multicomponent monooxygenases from Pseudomonas stutzeri OX1: molecular basis for catabolic adaptation of this microorganism to methylated aromatic compounds
Appl. Environ. Microbiol.
71
4736-4743
2005
Pseudomonas stutzeri, Pseudomonas stutzeri OX1
brenda
Cafaro, V.; Notomista, E.; Capasso, P.; Di Donato, A.
Mutation of glutamic acid 103 of toluene o-xylene monooxygenase as a means to control the catabolic efficiency of a recombinant upper pathway for degradation of methylated aromatic compounds
Appl. Environ. Microbiol.
71
4744-4750
2005
Pseudomonas stutzeri, Pseudomonas stutzeri OX1
brenda
Kagle, J.; Hay, A.G.
Phenylacetylene reversibly inhibits the phenol hydroxylase of Pseudomonas sp. CF600 at high concentrations but is oxidized at lower concentrations
Appl. Microbiol. Biotechnol.
72
306-315
2006
Pseudomonas sp., Pseudomonas sp. CF 600
brenda
Merimaa, M.; Heinaru, E.; Liivak, M.; Vedler, E.; Heinaru, A.
Grouping of phenol hydroxylase and catechol 2,3-dioxygenase genes among phenol- and p-cresol-degrading Pseudomonas species and biotypes
Arch. Microbiol.
186
287-296
2006
Pseudomonas sp.
brenda
Sazinsky, M.H.; Dunten, P.W.; McCormick, M.S.; Didonato, A.; Lippard, S.J.
X-ray structure of a hydroxylase-regulatory protein complex from a hydrocarbon-oxidizing multicomponent monooxygenase, Pseudomonas sp. OX1 phenol hydroxylase
Biochemistry
45
15392-15404
2006
Pseudomonas sp., Pseudomonas sp. OX1
brenda