Information on EC 1.11.2.1 - unspecific peroxygenase

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The expected taxonomic range for this enzyme is: Eukaryota, Archaea

EC NUMBER
COMMENTARY hide
1.11.2.1
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RECOMMENDED NAME
GeneOntology No.
unspecific peroxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
RH + H2O2 = ROH + H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
halogenation
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hydroxylation
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oxygenation
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peroxygenation
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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.
CAS REGISTRY NUMBER
COMMENTARY hide
93229-67-5
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(1E)-prop-1-en-1-ylbenzene + H2O2
2-methyl-3-phenyloxirane + H2O
show the reaction diagram
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71% conversion, 7% enantiomeric excess
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?
(1Z)-prop-1-en-1-ylbenzene + H2O2
2-methyl-3-phenyloxirane + H2O
show the reaction diagram
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96% conversion, 29% enantiomeric excess
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?
(R)-(+)-limonene + H2O2
? + H2O
show the reaction diagram
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76% epoxide products
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?
(R)-2-phenoxyproprionic acid + H2O2
(R)-2-(4-hydroxyphenoxy)propionic acid + H2O
show the reaction diagram
(S)-(-)-limonene + H2O2
? + H2O
show the reaction diagram
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85% epoxide products
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?
1,2,3,4-tetrahydronaphthalene + H2O2
(1R)-1,2,3,4-tetrahydronaphthalen-1-ol
show the reaction diagram
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85% conversion, 99% enantiomeric excess
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?
1,2-dihydronaphthalene + H2O2
1,2-dihydronaphthalene oxide
show the reaction diagram
1,4-dimethoxybenzene + H2O2
4-methoxyphenol + formaldehyde + H2O
show the reaction diagram
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?
1,4-dimethoxybenzene + H2O2
4-methoxyphenol + H2O
show the reaction diagram
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?
1,4-dimethoxybenzene + H2O2
?
show the reaction diagram
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?
1,4-dioxane + H2O2
2-(2-hydroxyethoxy)acetaldehyde + H2O
show the reaction diagram
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?
1-(methoxymethyl)-4-nitrobenzene + H2O2
4-nitrobenzaldehyde + methanol + H2O
show the reaction diagram
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?
1-butene + H2O2
but-3-en-2-ol + 2-ethyloxirane + H2O
show the reaction diagram
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75% epoxide product
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?
1-heptene + H2O2
hept-1-en-3-ol + 2-pentyloxirane + H2O
show the reaction diagram
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88% epoxide product
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?
1-hexene + H2O2
hex-1-en-3-ol + 2-butyloxirane + H2O
show the reaction diagram
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50% epoxide product
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?
1-methyl-1-cyclohexene + H2O2
3-methylcyclohex-3-en-1-ol + 1-methyl-7-oxabicyclo[4.1.0]heptane + H2O
show the reaction diagram
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70% epoxide product
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?
1-methyl-1H-indene + H2O2
(1aS,6aR)-6-methyl-6,6a-dihydro-1aH-indeno[1,2-b]oxirene + H2O
show the reaction diagram
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96% conversion, 2.3% enantiomeric excess
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?
1-methylnaphthalene + H2O2
monohydroxylated 1-methylnaphthalene + dihydroxylated 1- methylnaphthalene + H2O
show the reaction diagram
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monohydroxylated 1-methylnaphthalene and dihydroxylated 1-methylnaphthalene are the main metabolites
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?
1-methylnaphthalene + H2O2
monohydroxylated 1-methylnaphthalene + dihydroxylated 1-methylnaphthalene + H2O
show the reaction diagram
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monohydroxylated 1-methylnaphthalene and dihydroxylated 1-methylnaphthalene are the main metabolites
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?
1-octene + H2O2
oct-1-en-3-ol + 2-hexyloxirane + H2O
show the reaction diagram
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55% epoxide product
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?
1-pentene + H2O2
pent-1-en-3-ol + 2-propyloxirane + H2O
show the reaction diagram
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31% epoxide product
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?
1-pyrenol + H2O2
1,8-dihydroxypyrene + 1,6-dihydroxypyrene + H2O
show the reaction diagram
2 2,6-dimethoxyphenol + 2 H2O2
coerulignone + 2 H2O
show the reaction diagram
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?
2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O2
?
show the reaction diagram
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?
2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O2
? + H2O
show the reaction diagram
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?
2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O2
oxidized 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O
show the reaction diagram
2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate) + H2O2
?
show the reaction diagram
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?
2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate) + H2O2
oxidized 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate) + H2O
show the reaction diagram
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?
2,3-dihydro-1H-indene + H2O2
(1R)-2,3-dihydro-1H-inden-1-ol + H2O
show the reaction diagram
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77% conversion, 87% enantiomeric excess
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?
2,3-dimethyl-2-butene + H2O2
2,2,3,3-tetramethyloxirane + H2O
show the reaction diagram
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sole product
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?
2,3-dimethylbutane + H2O2
2,3-dimethyl-butan-2-ol + H2O
show the reaction diagram
2,6-dimethoxyphenol + H2O2
?
show the reaction diagram
2,6-dimethoxyphenol + H2O2
cerugilone + H2O
show the reaction diagram
2,6-dimethoxyphenol + H2O2
ceruglignone + H2O
show the reaction diagram
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?
2,6-dimethoxyphenol + H2O2
coerulignone + H2O
show the reaction diagram
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?
2,6-dimethoxyphenol + H2O2
oxidized 2,6-dimethoxyphenol + H2O
show the reaction diagram
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?
2-(propan-2-yloxy)propane + H2O2
propan-2-one + propan-2-ol + H2O
show the reaction diagram
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?
2-chloropyridine + H2O2
2-chloropyridine N-oxide + H2O
show the reaction diagram
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26.1% conversion compared to pyridine
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?
2-methyl-2-butene + H2O2
2,2,3-trimethyloxirane + H2O
show the reaction diagram
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sole product
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?
2-methyl-2-butene + H2O2
2,3-epoxy-2-methylbutane + H2O
show the reaction diagram
2-methylnaphthalene + H2O2
2-naphthoic acid + monohydroxylated 2-methylnaphthalene + 2-naphthaldehyde + 2-naphthalene-methanol + monohydroxylated 2-naphthaldehyde + monohydroxylated 2-naphthoic acid + monhydroxylated 2-napthalenemethanol + dihydroxylated 2-napthalenemethanol + H2O
show the reaction diagram
2-methylpropene + H2O2
2,2-dimethyloxirane + H2O
show the reaction diagram
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sole product
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?
2-phenoxypropionic acid + H2O2
(R)-2-(4-hydroxyphenoxy)propionic acid + H2O
show the reaction diagram
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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%
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?
3,4-dimethoxybenzyl alcohol + H2O2
3,4-dimethoxybenzaldehyde + H2O
show the reaction diagram
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?
3,4-dimethoxybenzylmethyl ether + H2O2
3,4-dimethoxybenzaldehyde + methanol + H2O
show the reaction diagram
3,5-dimethylpyridine + H2O2
5-methyl-nicotinic alcohol + 5-methyl-nicotinic aldehyde + 3,5-dimethylpyridine N-oxide + H2O
show the reaction diagram
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143.4% conversion compared to pyridine
3,5-dimethylpyridine N-oxide is less than 1% of the converted substrate
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?
3-bromopyridine + H2O2
3-bromopyridine N-oxide + H2O
show the reaction diagram
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61.8% conversion compared to pyridine
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?
3-chloropyridine + H2O2
3-chloropyridine N-oxide + nicotinic alcohol + nicotinic aldehyde + nicotinic acid + H2O
show the reaction diagram
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47.2% conversion compared to pyridine
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?
3-cyanopyridine + H2O2
3-cyanopyridine N-oxide + H2O
show the reaction diagram
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moderate substrate with 25.4% conversion compared to pyridine
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?
3-fluoropyridine + H2O2
3-fluoropyridine N-oxide + H2O
show the reaction diagram
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39.4% conversion compared to pyridine
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?
3-iodopyridine + H2O2
3-iodopyridine N-oxide + H2O
show the reaction diagram
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3-iodopyridine is slightly better oxidized than unsubstituted pyridine (102.2% conversion)
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?
3-methylpyridine + H2O2
3-methylpyridine N-oxide + H2O
show the reaction diagram
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98.4% conversion compared to pyridine
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?
3-nitropyridine + H2O2
3-nitropyridine N-oxide + H2O
show the reaction diagram
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moderate substrate with 5.4% conversion compared to pyridine
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?
4-chloropyridine + H2O2
4-chloropyridine N-oxide + H2O
show the reaction diagram
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4-chloropyridine is slightly better oxidized than unsubstituted pyridine (102.9% conversion)
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?
4-ethoxy-3-methoxybenzyl alcohol + H2O2
4-ethoxy-3-methoxybenzaldehyde + H2O
show the reaction diagram
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?
4-ethylbenzoic acid + H2O2
?
show the reaction diagram
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?
4-isoprophylbenzoic acid + H2O2
?
show the reaction diagram
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?
4-methyl-1-cyclohexene + H2O2
3-methyl-7-oxabicyclo[4.1.0]heptane + 6-methylcyclohex-2-en-1-ol + H2O
show the reaction diagram
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70% epoxide product
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?
4-nitroanisole + H2O2
formaldehyde + 4-nitrophenol + H2O
show the reaction diagram
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?
4-nitrobenzaldehyde + H2O2
4-nitrobenzoic acid + H2O
show the reaction diagram
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?
4-nitrobenzyl alcohol + H2O2
4-nitrobenzaldehyde + H2O
show the reaction diagram
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?
4-nitrophenol + H2O2
4-nitrocatechol + H2O
show the reaction diagram
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?
4-nitrophenoxycarboxylic acid + H2O2
?
show the reaction diagram
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?
4-nitrotoluene + H2O2
4-nitrobenzyl alcohol + H2O
show the reaction diagram
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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
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?
5-hydroxymethylfurfural + H2O2
2,5-furandicarboxylic acid + H2O
show the reaction diagram
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + H2O
show the reaction diagram
5-nitro-1,3-benzodioxole + H2O2
?
show the reaction diagram
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?
5-nitro-1,3-benzodioxole + H2O2
oxidized 5-nitro-1,3-benzodioxole + H2O
show the reaction diagram
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?
5-nitrobenzodioxole + H2O2
4-nitrocatechol + formic acid + H2O
show the reaction diagram
5-nitrobenzodioxole + H2O2
4-nitrocatechol + H2O
show the reaction diagram
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-
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?
acetanilide + H2O2
paracetamol + H2O
show the reaction diagram
anisaldehyde + H2O2
? + H2O
show the reaction diagram
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?
anisyl alcohol + H2O2
anisaldehyde + H2O
show the reaction diagram
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?
anthracene + H2O2
mono-hydroxylated anthracene + dihydroxylated anthracene
show the reaction diagram
benzaldehyde + H2O2
benzoic acid + H2O
show the reaction diagram
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-
-
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?
benzene + H2O2
phenol + H2O
show the reaction diagram
benzyl alcohol + H2O2
benzaldehyde + H2O
show the reaction diagram
carbamazepine + H2O2
3-hydroxycarbamazepine + H2O
show the reaction diagram
cholecalciferol + H2O2
25-hydroxycholecalciferol + 24-hydroxycholecalciferol + 26,27-hydroxycholecalciferol + H2O
show the reaction diagram
cis-2-butene + H2O2
2,3-dimethyloxirane + H2O
show the reaction diagram
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sole product
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?
cyclohexane + H2O2
? + H2O
show the reaction diagram
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?
cyclohexane + H2O2
cyclohexanol + cyclohexanone + ?
show the reaction diagram
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-
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?
cyclohexane + H2O2
cyclohexanol + H2O
show the reaction diagram
cyclohexanol + H2O2
cyclohexanone + H2O
show the reaction diagram
cyclohexene + H2O2
cyclohex-2-en-1-ol + 7-oxabicyclo[4.1.0]heptane + H2O
show the reaction diagram
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55% epoxide product
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?
daidzein + H2O2
6-hydroxydaidzein + H2O
show the reaction diagram
dibenzofuran + H2O2
3-hydroxy-dibenzofuran + monohydroxylated dibenzofuran + 2,3-dihydroxydibenzofuran + 3,7-dihydroxydibenzofuran + dihydroxylated dibenzofuran + trihydroxylated dibenzofuran + H2O
show the reaction diagram
dibenzothiophene + H2O2
?
show the reaction diagram
diclofenac + H2O2
4'-hydroxydiclofenac + H2O
show the reaction diagram
diclofenac + H2O2
?
show the reaction diagram
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-
-
?
diethyl ether + H2O2
acetaldehyde + ethanol + H2O
show the reaction diagram
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?
diethyl ether + H2O2
ethanol + acetaldehyde + H2O
show the reaction diagram
dimethoxy-5-nitrobenzene + H2O2
?
show the reaction diagram
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-
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?
dimethylene-5-nitrobenzene + H2O2
?
show the reaction diagram
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?
ergocalciferol + H2O2
25-hydroxyergocalciferol + H2O
show the reaction diagram
ethylbenzene + H2O2
(R)-1-phenylethanol
show the reaction diagram
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95% conversion, 99% enantiomeric excess
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?
ethylbenzene + H2O2
(R)-phenylethanol + H2O
show the reaction diagram
ethylbenzene + H2O2
1-phenylethanol + H2O
show the reaction diagram
flavone + H2O2
6-hydroxyflavone + H2O
show the reaction diagram
fluorene + H2O2
2-hydroxyfluorene + 9-fluorenol + dihydroxylated fluorene + monohydroxylated fluorenone + trihydroxylated fluorene + H2O
show the reaction diagram
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?
fluorene + H2O2
9-fluorenone + 2-hydroxyfluorene + 9-fluorenol + dihydroxylated fluorene + monohydroxylated fluorenone + trihydroxylated fluorene + H2O
show the reaction diagram
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the enzyme oxygenates fluorene at the non-aromatic C9-carbon
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?
fluorene + H2O2
9-hydroxyfluorene + H2O
show the reaction diagram
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?
fluorene + H2O2
?
show the reaction diagram
lauric acid + H2O2
11-hydroxylauric acid + 10-hydroxylauric acid + H2O
show the reaction diagram
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57% omega-1 product, 43% omega-2 product
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lauric acid + H2O2
omega-1-hydroxylauric acid + omega-2-hydroxylauric acid + omega-hydroxylauric acid + H2O
show the reaction diagram
lidocaine + H2O2
monoglycinexylidede + glycinexylidide + H2O
show the reaction diagram
methyl 3,4-dimethoxybenzyl ether + H2O2
3,4-dimethoxybenzaldehyde + methanol + H2O
show the reaction diagram
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?
methyl 4-nitrobenzyl ether + H2O2
4-nitrobenzaldehyde + methanol + H2O
show the reaction diagram
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?
methyl benzoate + H2O2
?
show the reaction diagram
methyl myristate + H2O2
methyl 13-hydroxymyristate + methyl 12-hydroxymyristate + methyl 13-oxomyristate + methyl 12-oxomyristate + H2O
show the reaction diagram
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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
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?
methyl tert-butyl ether + H2O2
formaldehyde + tert-butanol + H2O
show the reaction diagram
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-
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?
myristic acid + H2O2
13-hydroxymyristic acid + 12-hydroxymyristic acid + H2O
show the reaction diagram
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49.5% omega-1 hydroxy product, 43% omega-2 hydroxy product, plus small amounts of corresponding keto products
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?
myristoleic acid + H2O2
12-hydroxymyristoleic acid + H2O
show the reaction diagram
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100% omega-2 hydroxy product
-
?
n-butylbenzene + H2O2
(R)-1-phenylbutanol
show the reaction diagram
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52% conversion, 40% enantiomeric excess
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?
n-heptane + H2O2
2-heptanol + 3-heptanol + H2O
show the reaction diagram
n-pentylbenzene + H2O2
1-phenylpentanol
show the reaction diagram
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8.4% conversion, 99% enantiomeric excess
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?
naphthalene + H2O2
1-naphthol + 2-naphthol + 1,4-naphthoquinone + H2O
show the reaction diagram
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the enzyme regioselectively hydroxylates naphthalene to 1-naphthol and traces of 2-naphthol (ratio 36:1)
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?
naphthalene + H2O2
1-naphthol + 2-naphthol + H2O
show the reaction diagram
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naphthalene is regioselectively converted into 1-naphthol and 2-naphthol at a ratio of 12:1
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?
naphthalene + H2O2
1-naphthol + H2O
show the reaction diagram
naphthalene + H2O2
?
show the reaction diagram
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-
?
naphthalene + H2O2
? + H2O
show the reaction diagram
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?
naphthalene + H2O2
naphthalene 1,2-oxide + H2O
show the reaction diagram
octyl octanoate + H2O2
octyl 7-hydroxyoctanoate + octyl 6-hydroxyoctanoate + H2O
show the reaction diagram
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49.7% omega-1 hydroxy product, 50.3% omega-2 hydroxy product
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?
oleic acid + H2O2
17-hydroxyoleic acid + 16-hydroxyoleic acid + H2O
show the reaction diagram
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33% omega-1 hydroxy product, 66% omega-2 hydroxy product
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?
palmitic acid + H2O2
15-hydroxypalmitic acid + 14-hydroxypalmitic acid + H2O
show the reaction diagram
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38.4% omega-1 hydroxy product, 52.9% omega-2 hydroxy product, plus small amounts of corresponding keto products
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?
phenanthrene + H2O2
4-phenanthrol + 1-phenanthrol + 3-phenanthrol + dihydroxylated phenanthrol + H2O
show the reaction diagram
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the enzyme almost completely converts phenantrene within 6 h
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?
phenol + bromide
2-bromophenol + 4-bromophenol
show the reaction diagram
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phenol is brominated to 2- and 4-bromophenol (ratio 1:4)
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?
phenol + bromide
4-benzoquinone + 2-chlorophenol
show the reaction diagram
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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
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-
?
phenol + H2O2
hydroquinone + catechol + H2O
show the reaction diagram
phenol + KBr
4-bromophenol + 2-bromophenol
show the reaction diagram
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the Agrocybe aegerita peroxidase has also strong brominating activity
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?
propane + H2O2
isopropanol + H2O
show the reaction diagram
propene + H2O2
2-methyloxirane + H2O
show the reaction diagram
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100% epoxide product
-
?
propranolol + H2O2
5-hydroxypropranolol + H2O
show the reaction diagram
propylbenzene + H2O2
(R)-1-phenylpropanol
show the reaction diagram
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64% conversion, 99% enantiomeric excess
-
?
pyrene + H2O2
1-pyrenol + H2O
show the reaction diagram
pyridine + H2O2
pyridine N-oxide + H2O
show the reaction diagram
SAR548304 + H2O2
?
show the reaction diagram
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-
-
-
?
sildenafil + H2O2
desmethylsildenafil + H2O
show the reaction diagram
stearic acid + H2O2
17-hydroxystearic acid + 16-hydroxystearic acid + H2O
show the reaction diagram
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31.5% omega-1 hydroxy product, 50% omega-2 hydroxy product, plus small amounts of corresponding keto products
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?
testosterone + H2O2
17beta-hydroxy-4,5-epoxy-5beta-androstan-3-one + 16alpha,17beta-dihydroxyandrost-4-en-3-one + H2O
show the reaction diagram
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-
-
?
tetradecane + H2O2
2-hydroxytetradecane + 3-hydroxytetradecane + 2,13-dihydroxytetradecane + 2,12-dihydroxytetradecane + 3,12-dihydroxytetradecane + 12-hydroxy2-ketotetradecane
show the reaction diagram
-
-
reaction in 20% acetone, 120 min, 1% 2-hydroxytetradecane + 1.9% 3-hydroxytetradecane + 1.7% 2,13-dihydroxytetradecane + 9.5% 2,12-dihydroxytetradecane + 15% 3,12-dihydroxytetradecane + 70% 12-hydroxy-2-oxotetradecane. Reaction in 40% acetone, 120 min, 27% 2-hydroxytetradecane + 36% 3-hydroxytetradecane + 8.2% 2,13-dihydroxytetradecane + 14.2% 2,12-dihydroxytetradecane + 8.2% 3,12-dihydroxytetradecane + 6.3% 12-hydroxy2-ketotetradecane
-
?
tetradecanol + H2O2
13-hydroxytetradecanol + 12-hydroxytetradecanol + stearic acid + 13-hydroxystearic acid + 12-hydroxystearic acid + H2O
show the reaction diagram
-
-
30 min reaction, 6.4% 13-hydroxytetradecanol, 7.2% 12-hydroxytetradecanol, 75.8% stearic acid, 5.9% 13-hydroxystearic acid, 4.7%12-hydroxystearic acid. 120 min reaction, 4.1% 13-hydroxytetradecanol, 5.9% 12-hydroxytetradecanol, 47.2% stearic acid, 23.8% 13-hydroxystearic acid, 19.4% 12-hydroxystearic acid
-
?
tetrahydro-2H-pyran + H2O2
5-hydroxypentanal + H2O
show the reaction diagram
-
-
-
-
?
tetrahydrofuran + H2O2
4-hydroxybutanal + H2O
show the reaction diagram
toluene + H2O2
4-cresol + 2-cresol + methyl 4-benzoquinone + H2O
show the reaction diagram
-
-
-
-
?
toluene + H2O2
4-cresol + 2-cresol + methyl-4-benzoquinone + H2O
show the reaction diagram
-
-
-
-
?
toluene + H2O2
?
show the reaction diagram
-
-
-
-
?
toluene + H2O2
benzyl alcohol + benzaldehyde + benzoic acid + 2-cresol + 4-cresol + methylhydroquinone + H2O
show the reaction diagram
-
all peroxygenase fractions oxygenate toluene at both the side chain and the aromatic ring with a ratio of side chain versus aromatic hydroxylation of about 2:1 in all cases
-
-
?
toluene + H2O2
benzyl alcohol + H2O
show the reaction diagram
toluene + H2O2
o-cresol + p-cresol + H2O
show the reaction diagram
trans-2-butene + H2O2
2,3-dimethyloxirane + H2O
show the reaction diagram
-
-
sole product
-
?
vanillyl alcohol + H2O2
vanillaldehyde + H2O
show the reaction diagram
-
-
-
-
?
veratraldehyde + H2O2
veratric acid + H2O
show the reaction diagram
-
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
show the reaction diagram
veratryl alcohol + H2O2 + H+
veratraldehyde + H2O
show the reaction diagram
additional information
?
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4-nitrotoluene
-
the low extent of 4-nitrotoluene oxidation is attributable to inhibition of the enzyme by the substrate
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
H2O2
-
in the presence of 5 mM veratryl alcohol, optimal activity is observed with 2 mM H2O2, but the enzyme still exhibits 35% of the maximum activity with 10 mM H2O2
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.43
1,2-dimethoxy-4-(methoxymethyl)benzene
-
pH 5.6, 22C
0.733 - 0.759
1,4-dimethoxybenzene
0.025 - 0.181
2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid)
0.037 - 0.049
2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate)
0.126 - 0.866
2,6-dimethoxyphenol
4.976
2-methyl-2-butene
-
pH 5.6, 22C
0.35 - 0.87
5-nitro-1,3-benzodioxole
3.6
Benzene
-
pH 7.0, temperature not specified in the publication
0.118 - 2.8
benzyl alcohol
0.397 - 18.4
Cyclohexane
1.844 - 6.571
Cyclohexanol
0.778 - 0.907
diclofenac
0.261 - 0.427
dimethylene-5-nitrobenzene
-
694
ethylbenzene
-
pH not specified in the publication, temperature not specified in the publication
0.486 - 81.4
H2O2
1.43
methyl 3,4-dimethoxybenzyl ether
-
in potassium phosphate buffer (50 mM, pH 7.0), at 23C
0.127 - 0.791
Naphthalene
480
propylbenzene
-
pH not specified in the publication, temperature not specified in the publication
0.069
Pyridine
2.1
tetrahydrofuran
-
in potassium phosphate buffer (50 mM, pH 7.0), at 23C
0.088 - 7.9
veratryl alcohol
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
720
1,2-dimethoxy-4-(methoxymethyl)benzene
-
pH 5.6, 22C
457 - 593
1,4-dimethoxybenzene
25 - 952
2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid)
123 - 283
2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate)
2 - 142
2,6-dimethoxyphenol
1257
2-methyl-2-butene
-
pH 5.6, 22C
192 - 498
5-nitro-1,3-benzodioxole
8
Benzene
-
pH 7.0, temperature not specified in the publication
62 - 524
benzyl alcohol
13 - 72
Cyclohexane
3 - 31
Cyclohexanol
371 - 582
diclofenac
271 - 322
dimethylene-5-nitrobenzene
-
410
ethylbenzene
-
pH not specified in the publication, temperature not specified in the publication
0.07 - 1910
H2O2
720
methyl 3,4-dimethoxybenzyl ether
-
in potassium phosphate buffer (50 mM, pH 7.0), at 23C
15 - 229
Naphthalene
194
propylbenzene
-
pH not specified in the publication, temperature not specified in the publication
0.21
Pyridine
0.26
testosterone
at pH 7.0 and 22C
33
tetrahydrofuran
-
in potassium phosphate buffer (50 mM, pH 7.0), at 23C
3 - 203
veratryl alcohol
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
500
1,2-dimethoxy-4-(methoxymethyl)benzene
-
pH 5.6, 22C
130 - 160
1,4-dimethoxybenzene
353 - 11424
2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid)
2510 - 7670
2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate)
5.85 - 540
2,6-dimethoxyphenol
250
2-methyl-2-butene
-
pH 5.6, 22C
320 - 748
5-nitro-1,3-benzodioxole
2.2
Benzene
-
pH 7.0, temperature not specified in the publication
124 - 525
benzyl alcohol
2 - 72
Cyclohexane
0.39 - 1.7
Cyclohexanol
160 - 210
diclofenac
81 - 160
dimethylene-5-nitrobenzene
-
590
ethylbenzene
-
pH not specified in the publication, temperature not specified in the publication
0.0016 - 500
H2O2
500
methyl 3,4-dimethoxybenzyl ether
-
in potassium phosphate buffer (50 mM, pH 7.0), at 23C
25.7 - 620
Naphthalene
405
propylbenzene
-
pH not specified in the publication, temperature not specified in the publication
3 - 3.04
Pyridine
1.6
testosterone
at pH 7.0 and 22C
11.6 - 386
veratryl alcohol
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.83
-
culture liquid, using veratryl alcohol as substrate, at pH 7.0 and 25C
3
-
peroxidase from culture liquid, at pH 7.0 in sodium citrate/phosphate buffer, using veratryl alcohol as substrate, at 25C
30.6
-
36.7fold purified enzyme fraction P II, using veratryl alcohol as substrate, at pH 7.0 and 25C
31.5
-
37.8fold purified enzyme fraction P I, using veratryl alcohol as substrate, at pH 7.0 and 25C
35
-
using veratryl alcohol as substrate, in 50 mM potassium phosphate buffer (pH 7.0), at 22C over 15 min
38.5
-
46.2fold purified enzyme fraction P III, using veratryl alcohol as substrate, at pH 7.0 and 25C
62
-
using veratryl alcohol as substrate, in 50 mM potassium phosphate buffer (pH 7.0), at 22C over 15 min
71.8
-
purified peroxidase, at pH 2.75 in phosphate buffer, using monochlorodimedone (Cl-) as substrate, at 25C
75
-
isoform P II, using veratryl alcohol as substrate, pH 7.0, temperature not specified in the publication
77
-
major enzyme form P I, after 33fold purification, using veratryl alchol as substrate, pH and temperature not specified in the publication
94
-
major enzyme form P II, after 40fold purification, using veratryl alchol as substrate, pH and temperature not specified in the publication
99.6
-
purified peroxidase, at pH 7.0 in sodium citrate/phosphate buffer, using 2,6-dimethoxyphenol as substrate, at 25C
103
-
major enzyme form P III, after 44fold purification, using veratryl alchol as substrate, pH and temperature not specified in the publication
165
-
peroxidase isozyme P II, after 55fold purification, at pH 7.0 in sodium citrate/phosphate buffer, using veratryl alcohol as substrate, at 25C
167
-
peroxidase isozyme P I, after 56fold purification, at pH 7.0 in sodium citrate/phosphate buffer, using veratryl alcohol as substrate, at 25C
217
-
purified enzyme, using naphthalene as substrate, pH and temperature not specified in the publication
234.2
-
purified peroxidase, at pH 7.0 in sodium citrate/phosphate buffer, using benzyl alcohol as substrate, at 25C
236.7
-
purified peroxidase, at pH 7.0 in sodium citrate/phosphate buffer, using benzaldehyde as substrate, at 25C
295.7
-
purified peroxidase, at pH 5.0 in sodium citrate/phosphate buffer, using 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate) as substrate, at 25C
354.3
-
purified peroxidase, at pH 2.75 in phosphate buffer, using monochlorodimedone (Br-) as substrate, at 25C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.4
-
optimum pH for 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid)
4.7
-
2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate) oxidation occurs in a narrow pH range (pH 2.0-6.5), with an acidic maximum around pH 4.7
5 - 8
-
activity related to 1-naphthol formation shows a broad pH optimum between 5.0 and 8.0
5
-
pH optimum for the oxidation of 2,2-azinobis-(3-ethylbenzothiazoline-6-sulfonate)
6
-
pH optimum for the oxidation of 2,6-dimethoxyphenol
6.2
-
the enzyme has two pH optima for the oxidation of benzyl alcohol (pH 6.2 and 7.2)
6.5
-
optimum pH for 5-nitro-1,3-benzodioxole
7.2
-
the enzyme has two pH optima for the oxidation of benzyl alcohol (pH 6.2 and 7.2)
7.5
-
pH optimum for the oxidation of veratryl alcohol
8
-
pH optimum for the oxidation of benzyl alcohol
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2.5 - 9
4 - 7.5
-
more than 50% activity between pH 4.0 and 7.5
4 - 8
-
more than 50% activity between pH 4.0 and 8.0
4.5 - 9
there is substantial activity loss outside the pH range of 4.5-9.0
5.4 - 8.4
-
for the reaction with methyl 3,4-dimethoxybenzyl ether
5.5 - 7.5
-
more than 50% activity between pH 5.5 and 7.5
6 - 9
-
pH 6.0: about 60% of maximal activity, pH 9.0: about 45% of maximal activity
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3.8
-
enzyme fraction P I shows two pI-values at 3.8 and 3.9, isoelectric focusing
3.9
-
enzyme fraction P I shows two pI-values at 3.8 and 3.9, isoelectric focusing
4
-
enzyme fraction P III, isoelectric focusing
4.2
-
enzyme fraction P II, isoelectric focusing
4.6 - 5.4
4.9 - 5.6
-
isozyme P II, isoelectric focusing
4.9 - 5.7
isoelectric focusing
5 - 5.3
-
three pI-bands between 5.0 and 5.3, major band at 5.3
5.3
-
main enzyme fraction P II, isoelectric focusing
5.5
mature protein without glycosylation, calculated from amino acid sequence
6.1
-
the final protein fraction had a molecular mass of 46 kDa but still consists of several incompletely separated proteins with slightly differing isoelectric points (pI 5.2, 5.6, 6.1), probably representing differently glycosylated isoforms
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
high expression in carbon- and nitrogen-rich media
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
32000
-
x * 32000, SDS-PAGE
35900
mature protein without glycosylation, calculated from amino acid sequence
37000
deglycosylated protein, SDS-PAGE
43000
-
enzyme fractions P II and P III, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor diffusion method, using ammonium sulfate as the precipitant a total of three suitable crystal forms are obtained at different pH values (PIIpH46 with 2.0 M ammonium sulfate in 100 mM TrisHCl pH 8.5, PIIpH56 with 2.4 M ammonium sulfate in 100 mM sodium citrate pH 5.6, and PIIpH85 with 2.0 M ammonium sulfate in 200 mM sodium acetate pH 4.6)
-
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3 - 9
-
substantial oxygenation of naphthalene still occurs at pH 3.0 and pH 9.0 (60 and 70% of the maximum conversion rate, respectively)
710955
5 - 10
-
highly stable within
723912
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
53
-
the enzyme shows 50% activity after 1 h at 53C
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
electrostatic immobilization of the negatively charged Agrocybe aegerita peroxygenase to chitosan-covered gold nanoparticles generates an ideal environment for the catalysis of peroxide reduction at a glassy carbon electrode
-
OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
an H2O2 concentration of 0.7 mM is most suitable regarding enzyme activity and stability
-
710926
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate precipitation, Phenyl Sepharose column chromatography, and Q-Source column chromatography
-
fast protein liquid chromatography
-
HiTrap SP column chromatography and BioSuite Q column chromatography
-
Mono Q column chromatography, Q-Sepharose column chromatography, and Superdex 75 gel filtration
Q Sepharose column chromatography, SP Sepharose column chromatography, and Mono S column chromatography
-
SP Sepharose column chromatography, Mono Q column chromatography, and Mono S column chromatography
-
ultrafiltration, ion exchange chromatography and gel filtration
ultrafiltration, Q Sepharose column chromatography, Mono Q column chromatography, and SEC column chromatography
-
ultrafiltration, SP Sepharose column chromatography, and Mono P column chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Pichia pastoris and Saccharomyces cerevisiae
-
expressed in Saccharomyces cerevisiae
-
expressed in Saccharomyces cerevisiae strain BJ5465
-
expression in Aspergillus oryzae
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
Agrocybe aegerita produces relatively high and stable peroxidase levels in complex liquid media based on soybeans
-
enzyme production can be specifically triggered in media containing soybean flour
highest enzyme levels are detected in the presence of soybean meal (60 g/l)
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
F12Y/A14V/R15G/A21D/V57A/L67F/V75I/I248V/F311L
-
the mutant enzyme exhibits enhanced activity, secretion and stability compared to the wild type enzyme
F12Y/A14V/R15GA21D/V57A/L67F/V75I/I248V/F311L
-
this mutant retains strong activity and stability, particularly in terms of temperature and the presence of co-solvents, compared to the wild type enzyme
G241D/R257K
-
the mutant displays a 2fold improvement in peroxygenase activity and half the peroxidative activity of the wild type enzyme
S226G
-
the mutant shows increased thermal stability compared to the wild type enzyme
T120V/S226G/T320N
-
the mutant shows reduced activity compared to the wild type enzyme
T120V/S226G/T320R
-
the mutant shows reduced activity compared to the wild type enzyme
F310A/A320Q
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
-
use of enzyme for biosensor applications. The substrate spectrum overlaps with those of cytochrome P450s and plant peroxidases which are relevant in environmental analysis and drug monitoring. After immobilization at a chitosan-capped gold-nanoparticle modified glassy carbon electrode, enzyme displays a pair of redox peaks with a midpoint potential of -278.5 mV vs. AgCl/AgCl at 1 M KCl for the Fe2+/Fe3+ redox couple of the heme-thiolate-containing protein. The signal is generated by the reduction of electrode-active reaction products e.g., p-benzoquinone and p-quinoneimine with electroenzymatic recycling of the analyte
additional information
-
Agrocybe aegerita peroxygenase is a particularly potent biocatalyst that fills the gap between cytochrome P450s and common heme peroxidases