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Information on EC 1.11.2.1 - unspecific peroxygenase
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1.11.2.1 unspecific peroxygenaseIUBMB Comments
A heme-thiolate protein (P-450). Enzymes of this type include glycoproteins secreted by agaric basidiomycetes. They catalyse the insertion of an oxygen atom from H2O2 into a wide variety of substrates, including aromatic rings such as naphthalene, toluene, phenanthrene, pyrene and p-nitrophenol, recalcitrant heterocycles such as pyridine, dibenzofuran, various ethers (resulting in O-dealkylation) and alkanes such as propane, hexane and cyclohexane. Reactions catalysed include hydroxylation, epoxidation, N-oxidation, sulfooxidation, O- and N-dealkylation, bromination and one-electron oxidations. They have little or no activity toward chloride. Mechanistically, the catalytic cycle of unspecific (mono)-peroxygenases combines elements of the "shunt" pathway of cytochrome P-450s (a side activity that utilizes a peroxide in place of dioxygen and NAD[P]H) and the classic heme peroxidase cycle.
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Word Map
- 1.11.2.1
- vanadium
- chloroperoxidase
-
peroxygenases
-
bromoperoxidase
-
peroxygenation
- marasmius
- curvularia
- monochlorodimedone
-
oxyfunctionalization
-
vanadium-dependent
- rotula
- fumago
-
vhpos
-
ascophyllum
- inaequalis
-
caldariomyces
- analysis
The expected taxonomic range for this enzyme is: Eukaryota, Archaea
Synonyms
haloperoxidase, unspecific peroxygenase, p450st, aromatic peroxygenase, extracellular peroxygenase, pada-i, agrocybe aegerita peroxidase, heme-thiolate peroxygenase, agrocybe aegerita peroxidase/peroxygenase, unspecific heme peroxygenase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Agrocybe aegerita peroxidase
APO
aromatic peroxygenase
extracellular peroxygenase
haloperoxidase-peroxygenase
mushroom peroxygenase
-
-
-
-
P450st
unspecific heme peroxygenase
UPO
Agrocybe aegerita peroxidase
-
-
-
-
Agrocybe aegerita peroxidase
-
P II, main isoform of Agrocybe aegerita peroxidase
aromatic peroxygenase
-
-
-
-
aromatic peroxygenase
-
-
haloperoxidase-peroxygenase
-
-
-
-
UPO
-
-
UPO
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
RH + H2O2 = ROH + H2O
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SYSTEMATIC NAME
IUBMB Comments
substrate:hydrogen peroxide oxidoreductase (RH-hydroxylating or -epoxidising)
A heme-thiolate protein (P-450). Enzymes of this type include glycoproteins secreted by agaric basidiomycetes. They catalyse the insertion of an oxygen atom from H2O2 into a wide variety of substrates, including aromatic rings such as naphthalene, toluene, phenanthrene, pyrene and p-nitrophenol, recalcitrant heterocycles such as pyridine, dibenzofuran, various ethers (resulting in O-dealkylation) and alkanes such as propane, hexane and cyclohexane. Reactions catalysed include hydroxylation, epoxidation, N-oxidation, sulfooxidation, O- and N-dealkylation, bromination and one-electron oxidations. They have little or no activity toward chloride. Mechanistically, the catalytic cycle of unspecific (mono)-peroxygenases combines elements of the "shunt" pathway of cytochrome P-450s (a side activity that utilizes a peroxide in place of dioxygen and NAD[P]H) and the classic heme peroxidase cycle.
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CAS REGISTRY NUMBER
COMMENTARY
93229-67-5
-
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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
(1E)-prop-1-en-1-ylbenzene + H2O2
2-methyl-3-phenyloxirane + H2O
-
-
71% conversion, 7% enantiomeric excess
-
?
(1Z)-prop-1-en-1-ylbenzene + H2O2
2-methyl-3-phenyloxirane + H2O
-
-
96% conversion, 29% enantiomeric excess
-
?
(prop-1-en-2-yl)benzene + H2O2
2-methyl-2-phenyloxirane + H2O
-
-
-
-
?
1,2,3,4-tetrahydronaphthalene + H2O2
(1R)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
85% conversion, 99% enantiomeric excess
-
?
1,2,3,4-tetrahydronaphthalene + H2O2
(1R)-1,2,3,4-tetrahydronaphthalen-1-ol + H2O
-
reaction is performed by mutant enzyme L60F (74% ee)
-
-
?
1,2,3,4-tetrahydronaphthalene + H2O2
3,4-dihydronaphthalen-1(2H)-one + H2O
-
reaction is performed by mutant enzyme F59Q/L60M/S159G/F154A
-
-
?
1,4-dimethoxybenzene + H2O2
4-methoxyphenol + formaldehyde + H2O
-
-
-
-
?
1-(methoxymethyl)-4-nitrobenzene + H2O2
4-nitrobenzaldehyde + methanol + H2O
-
-
-
-
?
1-butene + H2O2
but-3-en-2-ol + 2-ethyloxirane + H2O
-
-
75% epoxide product
-
?
1-chloro-4-ethenylbenzene + H2O2
(2R)-2-(4-chlorophenyl)oxirane + H2O
-
-
-
?
1-heptene + H2O2
hept-1-en-3-ol + 2-pentyloxirane + H2O
-
-
88% epoxide product
-
?
1-hexene + H2O2
hex-1-en-3-ol + 2-butyloxirane + H2O
-
-
50% epoxide product
-
?
1-methyl-1-cyclohexene + H2O2
3-methylcyclohex-3-en-1-ol + 1-methyl-7-oxabicyclo[4.1.0]heptane + H2O
-
-
70% epoxide product
-
?
1-methyl-1H-indene + H2O2
(1aS,6aR)-6-methyl-6,6a-dihydro-1aH-indeno[1,2-b]oxirene + H2O
-
-
96% conversion, 2.3% enantiomeric excess
-
?
1-methylcyclohexene + H2O2
1-methyl-7-oxabicyclo[4.1.0]heptane + H2O
-
-
-
-
?
1-methylnaphthalene + H2O2
monohydroxylated 1-methylnaphthalene + dihydroxylated 1-methylnaphthalene + H2O
1-octene + H2O2
oct-1-en-3-ol + 2-hexyloxirane + H2O
-
-
55% epoxide product
-
?
1-pentene + H2O2
pent-1-en-3-ol + 2-propyloxirane + H2O
-
-
31% epoxide product
-
?
10-hydroxy-alpha-damascone + H2O2
4-oxo-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-enal + H2O
10-hydroxy-beta-damascone + H2O2
4-oxo-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-2-enal + H2O
2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O2
? + H2O
-
-
-
-
?
2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O2
oxidized 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O
2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate) + H2O2
oxidized 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate) + H2O
2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate) + H2O2
oxidized 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate) + H2O + H2O
-
-
-
?
2,3-dihydro-1H-indene + H2O2
2,3-dihydro-1H-inden-1-one + H2O
-
reaction is performed by mutant enzyme L60F
-
-
?
2,3-dimethyl-2-butene + H2O2
2,2,3,3-tetramethyloxirane + H2O
-
-
sole product
-
?
2-(propan-2-yloxy)propane + H2O2
propan-2-one + propan-2-ol + H2O
-
-
-
-
?
2-bromonaphthalene + H2O2
6-bromonaphthalene-1,4-dione + 2-bromonaphthalene-1,4-dione + H2O
-
reaction is performed by mutant enzyme L60F/S159G/A161F
-
-
?
2-chloropyridine + H2O2
2-chloropyridine N-oxide + H2O
-
26.1% conversion compared to pyridine
-
-
?
2-methoxynaphthalene + H2O2
6-methoxynaphthalene-1,4-dione + H2O
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reaction is performed by mutant enzyme L60F/S159G/A161F
-
-
?
2-methyl-2-butene + H2O2
2,2,3-trimethyloxirane + H2O
-
-
sole product
-
?
2-methylnaphthalene + H2O2
2-methylnaphthalene-1,4-dione + H2O
-
reaction is performed by mutant enzyme L60F/S159G/A161F
-
-
?
2-methylnaphthalene + H2O2
2-naphthoic acid + monohydroxylated 2-methylnaphthalene + 2-naphthaldehyde + 2-naphthalene-methanol + monohydroxylated 2-naphthaldehyde + monohydroxylated 2-naphthoic acid + monohydroxylated 2-naphthalenemethanol + dihydroxylated 2-naphthalenemethanol + H2O
2-methylnaphthalene + H2O2
6-methyl-4a,8a-dihydronaphthalene-1,4-dione + H2O
-
reaction is performed by the wild type enzyme
-
-
?
2-methylnaphthalene + H2O2
naphthalen-2-ylmethanol + H2O
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reaction is performed by mutant enzyme L60F
-
-
?
2-phenoxypropionic acid + H2O2
(R)-2-(4-hydroxyphenoxy)propionic acid + H2O
-
the enzyme hydroxylates 2-phenoxypropionic acid regioselectively at the para-position
the reaction yields the R-isomer of 2-(4-hydroxyphenoxy)propionic acid with an enantiomeric excess of 60%
-
?
3,5-dimethylpyridine + H2O2
5-methyl-nicotinic alcohol + 5-methyl-nicotinic aldehyde + 3,5-dimethylpyridine N-oxide + H2O
-
143.4% conversion compared to pyridine
3,5-dimethylpyridine N-oxide is less than 1% of the converted substrate
-
?
3-bromopyridine + H2O2
3-bromopyridine N-oxide + H2O
-
61.8% conversion compared to pyridine
-
-
?
3-chloropyridine + H2O2
3-chloropyridine N-oxide + nicotinic alcohol + nicotinic aldehyde + nicotinic acid + H2O
-
47.2% conversion compared to pyridine
-
-
?
3-cyanopyridine + H2O2
3-cyanopyridine N-oxide + H2O
-
moderate substrate with 25.4% conversion compared to pyridine
-
-
?
3-fluoropyridine + H2O2
3-fluoropyridine N-oxide + H2O
-
39.4% conversion compared to pyridine
-
-
?
3-iodopyridine + H2O2
3-iodopyridine N-oxide + H2O
-
3-iodopyridine is slightly better oxidized than unsubstituted pyridine (102.2% conversion)
-
-
?
3-methylpyridine + H2O2
3-methylpyridine N-oxide + H2O
-
98.4% conversion compared to pyridine
-
-
?
3-nitropyridine + H2O2
3-nitropyridine N-oxide + H2O
-
moderate substrate with 5.4% conversion compared to pyridine
-
-
?
4-chloropyridine + H2O2
4-chloropyridine N-oxide + H2O
-
4-chloropyridine is slightly better oxidized than unsubstituted pyridine (102.9% conversion)
-
-
?
4-ethoxy-3-methoxybenzyl alcohol + H2O2
4-ethoxy-3-methoxybenzaldehyde + H2O
-
-
-
-
?
4-methyl-1-cyclohexene + H2O2
3-methyl-7-oxabicyclo[4.1.0]heptane + 6-methylcyclohex-2-en-1-ol + H2O
-
-
70% epoxide product
-
?
4-nitrotoluene + H2O2
4-nitrobenzyl alcohol + H2O
-
APO hydroxylates 4-nitrotoluene to 4-nitrobenzyl alcohol, then to 4-nitrobenzaldehyde and then to 4-nitrobenzoic acid. The reactions proceed stepwise with total conversions of 12% for 4-nitrotoluene
-
-
?
4-oxo-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-2-enal + H2O2
4-oxo-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-2-enoic acid + H2O
4-oxo-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-enal + H2O2
4-oxo-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-enoic acid + H2O
7,11-epoxymegastigma-5(6)-en-9-one + H2O2
4-hydroxy-7,11-epoxymegastigma-5(6)-en-9-one + H2O
alpha-damascone + H2O2
3-hydroxy-alpha-damascone + 10-hydroxy-alpha-damascone + 4-epoxy-alpha-damascone + H2O
beta-damascone + H2O2
4-hydroxy-beta-damascone + 10-hydroxy-beta-damascone + 3-hydroxy-beta-damascone + H2O
beta-ionone + H2O2
4-hydroxy-beta-ionone + 3-hydroxy-beta-ionone + 2-hydroxy-beta-ionone + 13-hydroxy-beta-ionone + 10-hydroxy-beta-ionone + H2O
cholecalciferol + H2O2
25-hydroxycholecalciferol + 24-hydroxycholecalciferol + 26,27-hydroxycholecalciferol + H2O
cyclohexane + H2O2
cyclohexanol + 7-oxabicyclo[4.1.0]heptane + H2O
-
-
-
-
?
cyclohexene + H2O2
cyclohex-2-en-1-ol + 7-oxabicyclo[4.1.0]heptane + H2O
-
-
55% epoxide product
-
?
dibenzofuran + H2O2
3-hydroxy-dibenzofuran + monohydroxylated dibenzofuran + 2,3-dihydroxydibenzofuran + 3,7-dihydroxydibenzofuran + dihydroxylated dibenzofuran + trihydroxylated dibenzofuran + H2O
docosa-4,7,10,13,16,19-hexaenoic acid + H2O2
19,20-epoxydocosa-4,7,10,13,16-pentaenoic acid + H2O
docosa-7,10,13,16,19-pentaenoic acid + H2O2
19,20-epoxydocosa-7,10,13,16-tetraenoic acid + H2O
docosa-7,10,13,16-tetraenoic acid + H2O2
16,17-epoxydocosa-7,10,13-trienoic acid + H2O
-
adrenic acid, more than 99% conversion
-
-
?
eicosa-5,8,11,14,17-pentaenoic acid + H2O2
17,18-epoxyeicosa-5,8,11,14-tetraenoic acid + H2O
eicosa-5,8,11,14-tetraenoic acid + H2O2
14,15-epoxyeicosa-5,8,11-trienoic acid + H2O
-
94% conversion
-
-
?
eicosa-8,11,14-trienoic acid + H2O2
14,15-epoxyeicosa-8,11-dienoic acid + H2O
-
dihomo-gamma-linoleic acid, 96% conversion
-
-
?
ethylbenzene + H2O2
(1R)-1-phenylethanol + acetophenone + H2O
39% conversion
-
-
?
ethylbenzene + H2O2
(R)-1-phenylethanol
-
-
95% conversion, 99% enantiomeric excess
-
?
fluorene + H2O2
2-hydroxyfluorene + 9-fluorenol + dihydroxylated fluorene + monohydroxylated fluorenone + trihydroxylated fluorene + H2O
-
-
-
-
?
fluorene + H2O2
9-fluorenone + 2-hydroxyfluorene + 9-fluorenol + dihydroxylated fluorene + monohydroxylated fluorenone + trihydroxylated fluorene + H2O
-
the enzyme oxygenates fluorene at the non-aromatic C9-carbon
-
-
?
heneicosa-6,9,12,15,18-pentaenoic acid + H2O2
18,19-epoxyheneicosa-6,9,12,15-tetraenoic acid + H2O
hexadeca-7,10,13-trienoic acid + H2O2
13,14-epoxyhexadeca-7,10-dienoic acid + H2O
-
more than 99% conversion
-
-
?
isophorone + H2O2
(S)-4-hydroxyisophorone + 7-hydroxyisophorone + 7-formylisophorone + 4-ketoisophorone + H2O
isophorone + H2O2
4-hydroxyisophorone + 4-ketoisophorone + 7-formylisophorone + H2O
-
84% conversion, reaction with 0.0001 mM enzyme and 2.5 mM H2O2
-
-
?
lauric acid + H2O2
11-hydroxylauric acid + 10-hydroxylauric acid + H2O
-
-
57% omega-1 product, 43% omega-2 product
-
?
lauric acid + H2O2
omega-1-hydroxylauric acid + omega-2-hydroxylauric acid + omega-hydroxylauric acid + H2O
methyl 3,4-dimethoxybenzyl ether + H2O2
3,4-dimethoxybenzaldehyde + methanol + H2O
-
-
-
-
?
methyl 4-nitrobenzyl ether + H2O2
4-nitrobenzaldehyde + methanol + H2O
-
-
-
-
?
methyl myristate + H2O2
methyl 13-hydroxymyristate + methyl 12-hydroxymyristate + methyl 13-oxomyristate + methyl 12-oxomyristate + H2O
-
-
21.1% omega-1 hydroxy product, 43.4% omega-2 hydroxy product, plus 24.3% omega-1 keto product, 11.3% omega-2 keto product
-
?
methyl tert-butyl ether + H2O2
formaldehyde + tert-butanol + H2O
-
-
-
-
?
myristic acid + H2O2
13-hydroxymyristic acid + 12-hydroxymyristic acid + H2O
-
-
49.5% omega-1 hydroxy product, 43% omega-2 hydroxy product, plus small amounts of corresponding keto products
-
?
myristoleic acid + H2O2
12-hydroxymyristoleic acid + H2O
-
-
100% omega-2 hydroxy product
-
?
n-butylbenzene + H2O2
(R)-1-phenylbutanol
-
-
52% conversion, 40% enantiomeric excess
-
?
n-pentylbenzene + H2O2
1-phenylpentanol
-
-
8.4% conversion, 99% enantiomeric excess
-
?
N-phthaloyl-phenethylamine + H2O2
2-(2-hydroxy-2-phenylethyl)-1H-isoindole-1,3(2H)-dione + H2O
naphthalene + H2O2
1-naphthol + 2-naphthol + 1,4-naphthoquinone + H2O
-
the enzyme regioselectively hydroxylates naphthalene to 1-naphthol and traces of 2-naphthol (ratio 36:1)
-
-
?
naphthalene + H2O2
1-naphthol + 2-naphthol + H2O
-
naphthalene is regioselectively converted into 1-naphthol and 2-naphthol at a ratio of 12:1
-
-
?
naphthalene + H2O2
naphthalene-1,4-dione + 2-hydroxynaphthalene-1,4-dione + H2O
-
reaction is performed by mutant enzyme F59Q/L60F/S159G
-
-
?
octadeca-6,9,12,15-tetraenoic acid + H2O2
15,16-epoxyoctadeca-6,9,12-trienoic acid + H2O
-
stearidonic acid, more than 99% conversion
-
-
?
octane + H2O2
3-octanol + 2-octanol + 4-octanol + H2O
-
-
-
-
?
octyl octanoate + H2O2
octyl 7-hydroxyoctanoate + octyl 6-hydroxyoctanoate + H2O
-
-
49.7% omega-1 hydroxy product, 50.3% omega-2 hydroxy product
-
?
oleic acid + H2O2
17-hydroxyoleic acid + 16-hydroxyoleic acid + H2O
-
-
33% omega-1 hydroxy product, 66% omega-2 hydroxy product
-
?
palmitic acid + H2O2
15-hydroxypalmitic acid + 14-hydroxypalmitic acid + H2O
-
-
38.4% omega-1 hydroxy product, 52.9% omega-2 hydroxy product, plus small amounts of corresponding keto products
-
?
phenanthrene + H2O2
4-phenanthrol + 1-phenanthrol + 3-phenanthrol + dihydroxylated phenanthrol + H2O
-
the enzyme almost completely converts phenantrene within 6 h
-
-
?
phenol + bromide
2-bromophenol + 4-bromophenol
-
phenol is brominated to 2- and 4-bromophenol (ratio 1:4)
-
-
?
phenol + chloride
4-benzoquinone + 2-chlorophenol
-
the chlorinating activity is by orders of magnitude lower than the brominating activity, 4-benzoquinone is the major product while only traces of 2-chlorophenol (1%) and no 4-chlorophenol are detectable
-
-
?
phenol + KBr
4-bromophenol + 2-bromophenol
-
the Agrocybe aegerita peroxidase has also strong brominating activity
-
-
?
pinosylvin + H2O2
oxyresveratrol + oxypinosylvin + resveratrol + H2O
-
-
-
-
?
propranolol + H2O2
5-hydroxypropranolol + H2O