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(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
-
-
-
-
?
(R)-(+)-limonene + H2O2
? + H2O
-
-
76% epoxide products
-
?
(R)-2-phenoxypropionic acid + H2O2
(R)-2-(4-hydroxyphenoxy)propionic acid + H2O
(S)-(-)-limonene + H2O2
? + H2O
-
-
85% epoxide products
-
?
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
-
-
?
1,2-dihydronaphthalene + H2O2
1,2-dihydronaphthalene oxide
1,4-dimethoxybenzene + H2O2
4-methoxyphenol + formaldehyde + H2O
-
-
-
-
?
1,4-dimethoxybenzene + H2O2
?
-
-
-
-
?
1,4-dioxane + H2O2
2-(2-hydroxyethoxy)acetaldehyde + 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
-
?
1-phenylethanol + H2O2
1-phenylethanone + H2O
-
-
-
?
1-pyrenol + H2O2
1,8-dihydroxypyrene + 1,6-dihydroxypyrene + H2O
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
11-deoxycortisol + H2O2
? + H2O
12-(4-nitrophenoxy)dodecanoic acid + H2O2
?
-
-
-
?
2 2,6-dimethoxyphenol + 2 H2O2
cerugilone + 2 H2O
2 2,6-dimethoxyphenol + 2 H2O2
cerulignone + 2 H2O
2 2,6-dimethoxyphenol + 2 H2O2
coerulignone + 2 H2O
-
-
-
-
?
2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) + H2O2
?
2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O2
?
-
-
-
-
?
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
?
-
-
-
-
?
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
(1R)-2,3-dihydro-1H-inden-1-ol + 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
-
?
2,3-dimethylbutane + H2O2
2,3-dimethyl-butan-2-ol + H2O
2,6-dimethoxyphenol + H2O2
?
2,6-dimethoxyphenol + H2O2
colored coerulignone + H2O
2,6-dimethoxyphenol + H2O2
oxidized 2,6-dimethoxyphenol + H2O
-
-
-
-
?
2-(benzyloxy)ethanol + H2O2
? + H2O
-
-
-
?
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-hydroxy-beta-ionone + H2O2
2-oxo-beta-ionone + H2O
2-methoxynaphthalene + H2O2
6-methoxynaphthalene-1,4-dione + H2O
-
reaction is performed by mutant enzyme L60F/S159G/A161F
-
-
?
2-methyl-2-butene + H2O2
2,2,3-trimethyloxirane + H2O
-
-
sole product
-
?
2-methyl-2-butene + H2O2
2,3-epoxy-2-methylbutane + H2O
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
-
reaction is performed by mutant enzyme L60F
-
-
?
2-methylpropene + H2O2
2,2-dimethyloxirane + H2O
-
-
sole product
-
?
2-oxindole + H2O2
5-hydroxy-2-oxindole + 6-hydroxy-2-oxindole + H2O
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%
-
?
3,4-dimethoxybenzyl alcohol + H2O2
3,4-dimethoxybenzaldehyde + H2O
3,4-dimethoxybenzylmethyl ether + H2O2
3,4-dimethoxybenzaldehyde + methanol + H2O
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-hydroxy-alpha-damascone + H2O2
3-oxo-alpha-damascone + H2O
3-hydroxy-alpha-ionone + H2O2
3-oxo-alpha-ionone + 3-hydroxy-2,3-didehydro-alpha-ionone
3-hydroxyindoline + H2O2
indoxyl + H2O
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-ethylbenzoic acid + H2O2
4-(1-hydroxyethyl)benzoic acid + H2O
-
-
-
-
?
4-ethylbenzoic acid + H2O2
?
-
-
-
?
4-hydroxy-beta-damascone + H2O2
4-oxo-beta-damascone + H2O
4-hydroxy-beta-ionone + H2O2
4-oxo-beta-ionone + H2O
4-hydroxy-trans-stilbene + H2O2
4,4'-dihydroxy-trans-stilbene + H2O
4-isopropylbenzoic acid + H2O2
?
-
-
-
?
4-methyl-1-cyclohexene + H2O2
3-methyl-7-oxabicyclo[4.1.0]heptane + 6-methylcyclohex-2-en-1-ol + H2O
-
-
70% epoxide product
-
?
4-nitroanisole + H2O2
formaldehyde + 4-nitrophenol + H2O
-
-
-
-
?
4-nitrobenzaldehyde + H2O2
4-nitrobenzoic acid + H2O
4-nitrobenzyl alcohol + H2O2
4-nitrobenzaldehyde + H2O
-
-
-
-
?
4-nitrophenol + H2O2
4-nitrocatechol + H2O
-
-
-
-
?
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
5-bromoindole + 5-bromoindoline + H2O2
5,5'-dibromoindigo + H2O
5-hydroxymethylfurfural + H2O2
2,5-furandicarboxylic acid + H2O
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + formic acid + H2O
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + H2O
5-nitro-1,3-benzodioxole + H2O2
?
6-bromoindole + H2O2
6-bromo-2-oxindole + 3-oxo-6-bromoindole + H2O
7,11-epoxymegastigma-5(6)-en-9-one + H2O2
4-hydroxy-7,11-epoxymegastigma-5(6)-en-9-one + H2O
acetanilide + H2O2
paracetamol + H2O
allylbenzylether + H2O2
? + H2O
lowest turnover number
-
-
?
alpha-damascone + H2O2
3-hydroxy-alpha-damascone + 10-hydroxy-alpha-damascone + 4-epoxy-alpha-damascone + H2O
alpha-ionone + H2O2
3-hydroxy-alpha-ionone + 4-epoxy-alpha-ionone + H2O
anisaldehyde + H2O2
? + H2O
-
-
-
-
?
anisyl alcohol + H2O2
anisaldehyde + H2O
-
-
-
-
?
anthracene + H2O2
mono-hydroxylated anthracene + dihydroxylated anthracene
benzaldehyde + H2O2
benzoic acid + H2O
-
-
-
-
?
benzene + H2O2
phenol + H2O
benzyl alcohol + H2O2
benzaldehyde + H2O
benzyloxyacetaldehyde + H2O2
? + H2O
high turnover number
-
-
?
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
carbamazepine + H2O2
3-hydroxycarbamazepine + H2O
cholecalciferol + H2O2
25-hydroxycholecalciferol + 24-hydroxycholecalciferol + 26,27-hydroxycholecalciferol + H2O
cis-2-butene + H2O2
2,3-dimethyloxirane + H2O
-
-
sole product
-
?
cortisone + H2O2
cortisone 21-gem-diol + cortisone 21-oic acid + adrenosterone + H2O
cortisone 21-al + H2O2
cortisone 21-oic acid + H2O
cyclohexane + H2O2
? + H2O
-
-
-
-
?
cyclohexane + H2O2
cyclohexanol + 7-oxabicyclo[4.1.0]heptane + H2O
-
-
-
-
?
cyclohexane + H2O2
cyclohexanol + cyclohexanone + ?
-
-
-
-
?
cyclohexane + H2O2
cyclohexanol + H2O
cyclohexanol + H2O2
cyclohexanone + H2O
cyclohexene + H2O2
7-oxabicyclo[4.1.0]heptane + H2O
-
-
-
-
?
cyclohexene + H2O2
cyclohex-2-en-1-ol + 7-oxabicyclo[4.1.0]heptane + H2O
-
-
55% epoxide product
-
?
cyclohexene + H2O2
cyclohexene oxide + H2O
-
-
-
?
daidzein + H2O2
6-hydroxydaidzein + H2O
dibenzofuran + H2O2
3-hydroxy-dibenzofuran + monohydroxylated dibenzofuran + 2,3-dihydroxydibenzofuran + 3,7-dihydroxydibenzofuran + dihydroxylated dibenzofuran + trihydroxylated dibenzofuran + H2O
dibenzothiophene + H2O2
?
dibenzylether + H2O2
? + H2O
highest turnover number
-
-
?
diclofenac + H2O2
4'-hydroxydiclofenac + H2O
diclofenac + H2O2
?
-
-
-
-
?
diethyl ether + H2O2
acetaldehyde + ethanol + H2O
-
-
-
-
?
diethyl ether + H2O2
ethanol + acetaldehyde + H2O
dimethoxy-5-nitrobenzene + H2O2
?
-
-
-
-
?
dimethylene-5-nitrobenzene + H2O2
?
-
-
-
-
?
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-11,14,17-trienoic acid + H2O2
17,18-epoxyeicosa-11,14-dienoic acid + H2O
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
-
-
?
ergocalciferol + H2O2
25-hydroxyergocalciferol + H2O
erucic acid + H2O2
? + H2O
ethenylbenzene + H2O2
(2S)-2-phenyloxirane + H2O
-
-
-
?
ethenylbenzene + H2O2
2-phenyloxirane + H2O
-
-
-
-
?
ethylbenzene + H2O2
(1R)-1-phenylethanol + acetophenone + H2O
39% conversion
-
-
?
ethylbenzene + H2O2
(R)-1-phenylethanol
-
-
95% conversion, 99% enantiomeric excess
-
?
ethylbenzene + H2O2
(R)-phenylethanol + H2O
ethylbenzene + H2O2
1-phenylethanol + H2O
flavone + H2O2
6-hydroxyflavone + H2O
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
-
-
?
fluorene + H2O2
9-hydroxyfluorene + H2O
-
-
-
-
?
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
-
-
?
indole + H2O2
2-oxindole + indoxyl + H2O
indole + H2O2
indigo + H2O
-
-
-
?
indoline + H2O2
3-hydroxyindoline + H2O
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
-
-
?
isophorone + H2O2
4-hydroxyisophorone + 4-ketoisophorone + H2O
isophorone + H2O2
4-ketoisophorone + H2O
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
lidocaine + H2O2
monoglycinexylidede + glycinexylidide + H2O
linoleic acid + H2O2
? + H2O
linoleic acid methyl ester + H2O2
? + 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
-
?
myristoleic acid + H2O2
? + H2O
n-butylbenzene + H2O2
(R)-1-phenylbutanol
-
-
52% conversion, 40% enantiomeric excess
-
?
n-heptane + H2O2
2-heptanol + 3-heptanol + H2O
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
1-naphthol + H2O
naphthalene + H2O2
? + H2O
-
-
-
-
?
naphthalene + H2O2
naphthalene 1,2-oxide + H2O
naphthalene + H2O2
naphthalene-1,4-dione + 2-hydroxynaphthalene-1,4-dione + H2O
-
reaction is performed by mutant enzyme F59Q/L60F/S159G
-
-
?
naphthalene + H2O2
naphthol + 1,4-naphthoquinone + H2O
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
-
?
oleic acid + H2O2
? + H2O
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
-
?
palmitoleic acid + H2O2
? + H2O
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 + H2O2
hydroquinone + catechol + H2O
phenol + KBr
4-bromophenol + 2-bromophenol
-
the Agrocybe aegerita peroxidase has also strong brominating activity
-
-
?
phenylbutane + H2O2
1-phenylbutan-1-ol + H2O
phenylethane + H2O2
1-phenylethan-1-ol + H2O
phenylpentane + H2O2
1-phenylpentan-1-ol + H2O
phenylpropane + H2O2
1-phenylpropan-1-ol + H2O
pinosylvin + H2O2
oxyresveratrol + oxypinosylvin + resveratrol + H2O
-
-
-
-
?
pinosylvin + H2O2
oxyresveratrol + resveratrol + H2O
-
-
-
?
prednisone + H2O2
? + H2O
propane + H2O2
isopropanol + H2O
propene + H2O2
2-methyloxirane + H2O
-
-
100% epoxide product
-
?
propranolol + H2O2
5-hydroxypropranolol + H2O
propylbenzene + H2O2
(R)-1-phenylpropanol
-
-
64% conversion, 99% enantiomeric excess
-
?
pyrene + H2O2
1-pyrenol + H2O
pyridine + H2O2
pyridine N-oxide + H2O
resveratrol + H2O2
oxyresveratrol + H2O
SAR548304 + H2O2
?
-
-
-
-
?
sildenafil + H2O2
N-desmethylsildenafil + formaldehyde + H2O
stearic acid + H2O2
17-hydroxystearic acid + 16-hydroxystearic acid + H2O
-
-
31.5% omega-1 hydroxy product, 50% omega-2 hydroxy product, plus small amounts of corresponding keto products
-
?
styrene + H2O2
styrene oxide + H2O
testosterone + H2O2
17beta-hydroxy-4,5-epoxy-5beta-androstan-3-one + 16alpha,17beta-dihydroxyandrost-4-en-3-one + H2O
-
-
-
?
tetracosa-6,9,12,15,18,21-hexaenoic acid + H2O2
21,22-epoxytetracosa-6,9,12,15,18-pentaenoic acid + H2O
-
nisinic acid, more than 99% conversion
-
-
?
tetradecane + H2O2
2-hydroxytetradecane + 3-hydroxytetradecane + 2,13-dihydroxytetradecane + 2,12-dihydroxytetradecane + 3,12-dihydroxytetradecane + 12-hydroxy2-ketotetradecane
-
-
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
-
-
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
-
-
-
-
?
tetrahydrofuran + H2O2
4-hydroxybutanal + H2O
toluene + H2O2
4-cresol + 2-cresol + methyl 4-benzoquinone + H2O
-
-
-
-
?
toluene + H2O2
4-cresol + 2-cresol + methyl-4-benzoquinone + H2O
-
-
-
-
?
toluene + H2O2
?
-
-
-
-
?
toluene + H2O2
benzyl alcohol + benzaldehyde + benzoic acid + 2-cresol + 4-cresol + methylhydroquinone + H2O
-
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
toluene + H2O2
o-cresol + p-cresol + H2O
trans-2-butene + H2O2
2,3-dimethyloxirane + H2O
-
-
sole product
-
?
trans-stilbene + H2O2
4,4'-dihydroxy-trans-stilbene + tri-hydroxylated trans-stilbene + H2O
trans-stilbene + H2O2
trans-stilbene epoxide + H2O
-
-
-
-
?
vanillyl alcohol + H2O2
vanillaldehyde + H2O
-
-
-
-
?
veratraldehyde + H2O2
veratric acid + H2O
-
-
-
-
?
veratryl alcohol + H2O2
3,4-dimethoxybenzaldehyde + 3,4-dimethoxybenzoic acid + H2O
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
veratryl alcohol + H2O2 + H+
veratraldehyde + H2O
[(1Z)-prop-1-en-1-yl]benzene + H2O2
(2Z)-3-phenylprop-2-en-1-ol + (2Z)-3-phenylprop-2-enal + H2O
-
-
-
-
?
additional information
?
-
(R)-2-phenoxypropionic acid + H2O2
(R)-2-(4-hydroxyphenoxy)propionic acid + H2O
-
-
-
-
?
(R)-2-phenoxypropionic acid + H2O2
(R)-2-(4-hydroxyphenoxy)propionic acid + H2O
-
-
-
?
(R)-2-phenoxypropionic acid + H2O2
(R)-2-(4-hydroxyphenoxy)propionic acid + H2O
-
-
-
-
?
1,2-dihydronaphthalene + H2O2
1,2-dihydronaphthalene oxide
-
-
main product, plus some 1-hydroxy-1,2-dihydronaphthalene and 2-hydroxy-1,2-dihydronaphthalene
-
?
1,2-dihydronaphthalene + H2O2
1,2-dihydronaphthalene oxide
-
-
main product, plus some 1-hydroxy-1,2-dihydronaphthalene and 2-hydroxy-1,2-dihydronaphthalene. 1-Hydroxy-1,2-dihydronaphthalene and 2-hydroxy-1,2-dihydronaphthalene are aromatized and further epoxidized to naphthalene oxide, giving 95% 1-naphthol and 5% 2-naphthol as final products
-
?
1-methylnaphthalene + H2O2
monohydroxylated 1-methylnaphthalene + dihydroxylated 1-methylnaphthalene + H2O
-
-
monohydroxylated 1-methylnaphthalene and dihydroxylated 1-methylnaphthalene are the main metabolites
-
?
1-methylnaphthalene + H2O2
monohydroxylated 1-methylnaphthalene + dihydroxylated 1-methylnaphthalene + H2O
-
-
monohydroxylated 1-methylnaphthalene and dihydroxylated 1-methylnaphthalene are the main metabolites
-
?
1-pyrenol + H2O2
1,8-dihydroxypyrene + 1,6-dihydroxypyrene + H2O
-
-
-
-
?
1-pyrenol + H2O2
1,8-dihydroxypyrene + 1,6-dihydroxypyrene + H2O
-
-
-
-
?
10-hydroxy-alpha-damascone + H2O2
4-oxo-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-enal + H2O
-
-
-
-
?
10-hydroxy-alpha-damascone + H2O2
4-oxo-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-enal + H2O
-
-
-
-
?
10-hydroxy-alpha-damascone + H2O2
4-oxo-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-enal + H2O
-
-
-
-
?
10-hydroxy-alpha-damascone + H2O2
4-oxo-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-enal + H2O
-
-
-
-
?
10-hydroxy-alpha-damascone + H2O2
4-oxo-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-enal + H2O
-
-
-
-
?
10-hydroxy-alpha-damascone + H2O2
4-oxo-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-enal + H2O
-
-
-
-
?
10-hydroxy-alpha-damascone + H2O2
4-oxo-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-enal + H2O
-
-
-
-
?
10-hydroxy-alpha-damascone + H2O2
4-oxo-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-enal + H2O
-
-
-
-
?
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
-
-
-
-
?
10-hydroxy-beta-damascone + H2O2
4-oxo-4-(2,6,6-trimethylcyclohex-1-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
-
-
-
-
?
10-hydroxy-beta-damascone + H2O2
4-oxo-4-(2,6,6-trimethylcyclohex-1-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
-
-
-
-
?
10-hydroxy-beta-damascone + H2O2
4-oxo-4-(2,6,6-trimethylcyclohex-1-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
-
-
-
-
?
10-hydroxy-beta-damascone + H2O2
4-oxo-4-(2,6,6-trimethylcyclohex-1-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
-
-
-
-
?
11-deoxycortisol + H2O2
? + H2O
Reichstein's substance S
-
-
?
11-deoxycortisol + H2O2
? + H2O
-
Reichstein's substance S
-
-
?
11-deoxycortisol + H2O2
? + H2O
-
Reichstein's substance S
-
-
?
2 2,6-dimethoxyphenol + 2 H2O2
cerugilone + 2 H2O
-
-
-
-
?
2 2,6-dimethoxyphenol + 2 H2O2
cerugilone + 2 H2O
-
-
-
?
2 2,6-dimethoxyphenol + 2 H2O2
cerugilone + 2 H2O
-
-
-
-
?
2 2,6-dimethoxyphenol + 2 H2O2
cerulignone + 2 H2O
-
-
-
-
?
2 2,6-dimethoxyphenol + 2 H2O2
cerulignone + 2 H2O
-
-
-
?
2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) + H2O2
?
-
-
-
-
?
2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) + H2O2
?
-
-
-
?
2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O2
oxidized 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O
-
-
-
?
2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O2
oxidized 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O
-
-
-
?
2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O2
oxidized 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O
-
-
-
-
?
2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O2
oxidized 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O
-
-
-
-
?
2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O2
oxidized 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O
-
-
-
-
?
2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O2
oxidized 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O
-
-
-
?
2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + H2O2
oxidized 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) + 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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
2,3-dihydro-1H-indene + H2O2
(1R)-2,3-dihydro-1H-inden-1-ol + H2O
-
-
77% conversion, 87% enantiomeric excess
-
?
2,3-dihydro-1H-indene + H2O2
(1R)-2,3-dihydro-1H-inden-1-ol + H2O
-
reaction is performed by mutant enzyme L60F (95% ee)
-
-
?
2,3-dimethylbutane + H2O2
2,3-dimethyl-butan-2-ol + H2O
-
-
-
-
?
2,3-dimethylbutane + H2O2
2,3-dimethyl-butan-2-ol + H2O
-
-
-
?
2,3-dimethylbutane + H2O2
2,3-dimethyl-butan-2-ol + H2O
-
-
-
-
?
2,6-dimethoxyphenol + H2O2
?
-
-
-
-
?
2,6-dimethoxyphenol + H2O2
?
-
-
-
-
?
2,6-dimethoxyphenol + H2O2
?
-
-
-
?
2,6-dimethoxyphenol + H2O2
?
-
-
-
?
2,6-dimethoxyphenol + H2O2
?
-
-
-
-
?
2,6-dimethoxyphenol + H2O2
?
-
-
-
-
?
2,6-dimethoxyphenol + H2O2
?
-
-
-
-
?
2,6-dimethoxyphenol + H2O2
?
-
-
-
?
2,6-dimethoxyphenol + H2O2
?
-
-
-
-
?
2,6-dimethoxyphenol + H2O2
?
-
-
-
?
2,6-dimethoxyphenol + H2O2
?
-
-
-
-
?
2,6-dimethoxyphenol + H2O2
?
-
-
-
-
?
2,6-dimethoxyphenol + H2O2
?
-
-
-
-
?
2,6-dimethoxyphenol + H2O2
colored coerulignone + H2O
-
-
-
-
?
2,6-dimethoxyphenol + H2O2
colored coerulignone + H2O
-
-
-
-
?
2,6-dimethoxyphenol + H2O2
colored coerulignone + H2O
-
-
-
-
?
2,6-dimethoxyphenol + H2O2
colored coerulignone + H2O
-
-
-
-
?
2,6-dimethoxyphenol + H2O2
colored coerulignone + H2O
-
-
-
?
2,6-dimethoxyphenol + H2O2
colored coerulignone + H2O
-
-
-
?
2,6-dimethoxyphenol + H2O2
colored coerulignone + H2O
-
-
-
-
?
2-hydroxy-beta-ionone + H2O2
2-oxo-beta-ionone + H2O
-
-
-
-
?
2-hydroxy-beta-ionone + H2O2
2-oxo-beta-ionone + H2O
-
-
-
-
?
2-hydroxy-beta-ionone + H2O2
2-oxo-beta-ionone + H2O
-
-
-
-
?
2-hydroxy-beta-ionone + H2O2
2-oxo-beta-ionone + H2O
-
-
-
-
?
2-hydroxy-beta-ionone + H2O2
2-oxo-beta-ionone + H2O
-
-
-
-
?
2-hydroxy-beta-ionone + H2O2
2-oxo-beta-ionone + H2O
-
-
-
-
?
2-hydroxy-beta-ionone + H2O2
2-oxo-beta-ionone + H2O
-
-
-
-
?
2-hydroxy-beta-ionone + H2O2
2-oxo-beta-ionone + H2O
-
-
-
-
?
2-hydroxy-beta-ionone + H2O2
2-oxo-beta-ionone + H2O
-
-
-
-
?
2-methyl-2-butene + H2O2
2,3-epoxy-2-methylbutane + H2O
-
-
-
-
?
2-methyl-2-butene + H2O2
2,3-epoxy-2-methylbutane + H2O
-
-
-
?
2-methyl-2-butene + H2O2
2,3-epoxy-2-methylbutane + H2O
-
-
-
-
?
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-naphthoic acid and monohydroxylated 2-methylnaphthalenes are the main metabolites
-
?
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-naphthoic acid and monohydroxylated 2-methylnaphthalenes are the main metabolites
-
?
2-oxindole + H2O2
5-hydroxy-2-oxindole + 6-hydroxy-2-oxindole + H2O
-
-
-
-
?
2-oxindole + H2O2
5-hydroxy-2-oxindole + 6-hydroxy-2-oxindole + H2O
-
-
-
-
?
2-oxindole + H2O2
5-hydroxy-2-oxindole + 6-hydroxy-2-oxindole + H2O
-
-
-
-
?
3,4-dimethoxybenzyl alcohol + H2O2
3,4-dimethoxybenzaldehyde + H2O
-
-
-
-
?
3,4-dimethoxybenzyl alcohol + H2O2
3,4-dimethoxybenzaldehyde + H2O
-
-
-
?
3,4-dimethoxybenzylmethyl ether + H2O2
3,4-dimethoxybenzaldehyde + methanol + H2O
-
-
-
-
?
3,4-dimethoxybenzylmethyl ether + H2O2
3,4-dimethoxybenzaldehyde + methanol + H2O
-
-
-
?
3,4-dimethoxybenzylmethyl ether + H2O2
3,4-dimethoxybenzaldehyde + methanol + H2O
-
-
-
-
?
3-hydroxy-alpha-damascone + H2O2
3-oxo-alpha-damascone + H2O
-
-
-
-
?
3-hydroxy-alpha-damascone + H2O2
3-oxo-alpha-damascone + H2O
-
-
-
-
?
3-hydroxy-alpha-damascone + H2O2
3-oxo-alpha-damascone + H2O
-
-
-
-
?
3-hydroxy-alpha-damascone + H2O2
3-oxo-alpha-damascone + H2O
-
-
-
-
?
3-hydroxy-alpha-damascone + H2O2
3-oxo-alpha-damascone + H2O
-
-
-
-
?
3-hydroxy-alpha-damascone + H2O2
3-oxo-alpha-damascone + H2O
-
-
-
-
?
3-hydroxy-alpha-damascone + H2O2
3-oxo-alpha-damascone + H2O
-
-
-
-
?
3-hydroxy-alpha-damascone + H2O2
3-oxo-alpha-damascone + H2O
-
-
-
-
?
3-hydroxy-alpha-damascone + H2O2
3-oxo-alpha-damascone + H2O
-
-
-
-
?
3-hydroxy-alpha-ionone + H2O2
3-oxo-alpha-ionone + 3-hydroxy-2,3-didehydro-alpha-ionone
-
-
-
-
?
3-hydroxy-alpha-ionone + H2O2
3-oxo-alpha-ionone + 3-hydroxy-2,3-didehydro-alpha-ionone
-
-
-
-
?
3-hydroxy-alpha-ionone + H2O2
3-oxo-alpha-ionone + 3-hydroxy-2,3-didehydro-alpha-ionone
-
-
-
-
?
3-hydroxy-alpha-ionone + H2O2
3-oxo-alpha-ionone + 3-hydroxy-2,3-didehydro-alpha-ionone
-
-
-
-
?
3-hydroxy-alpha-ionone + H2O2
3-oxo-alpha-ionone + 3-hydroxy-2,3-didehydro-alpha-ionone
-
-
-
-
?
3-hydroxy-alpha-ionone + H2O2
3-oxo-alpha-ionone + 3-hydroxy-2,3-didehydro-alpha-ionone
-
-
-
-
?
3-hydroxy-alpha-ionone + H2O2
3-oxo-alpha-ionone + 3-hydroxy-2,3-didehydro-alpha-ionone
-
-
-
-
?
3-hydroxy-alpha-ionone + H2O2
3-oxo-alpha-ionone + 3-hydroxy-2,3-didehydro-alpha-ionone
-
-
-
-
?
3-hydroxy-alpha-ionone + H2O2
3-oxo-alpha-ionone + 3-hydroxy-2,3-didehydro-alpha-ionone
-
-
-
-
?
3-hydroxyindoline + H2O2
indoxyl + H2O
-
-
-
-
?
3-hydroxyindoline + H2O2
indoxyl + H2O
-
-
-
-
?
3-hydroxyindoline + H2O2
indoxyl + H2O
-
-
-
-
?
4-hydroxy-beta-damascone + H2O2
4-oxo-beta-damascone + H2O
-
-
-
-
?
4-hydroxy-beta-damascone + H2O2
4-oxo-beta-damascone + H2O
-
-
-
-
?
4-hydroxy-beta-damascone + H2O2
4-oxo-beta-damascone + H2O
-
-
-
-
?
4-hydroxy-beta-damascone + H2O2
4-oxo-beta-damascone + H2O
-
-
-
-
?
4-hydroxy-beta-damascone + H2O2
4-oxo-beta-damascone + H2O
-
-
-
-
?
4-hydroxy-beta-damascone + H2O2
4-oxo-beta-damascone + H2O
-
-
-
-
?
4-hydroxy-beta-ionone + H2O2
4-oxo-beta-ionone + H2O
-
-
-
-
?
4-hydroxy-beta-ionone + H2O2
4-oxo-beta-ionone + H2O
-
-
-
-
?
4-hydroxy-beta-ionone + H2O2
4-oxo-beta-ionone + H2O
-
-
-
-
?
4-hydroxy-beta-ionone + H2O2
4-oxo-beta-ionone + H2O
-
-
-
-
?
4-hydroxy-beta-ionone + H2O2
4-oxo-beta-ionone + H2O
-
-
-
-
?
4-hydroxy-beta-ionone + H2O2
4-oxo-beta-ionone + H2O
-
-
-
-
?
4-hydroxy-trans-stilbene + H2O2
4,4'-dihydroxy-trans-stilbene + H2O
-
-
-
-
?
4-hydroxy-trans-stilbene + H2O2
4,4'-dihydroxy-trans-stilbene + H2O
-
-
-
-
?
4-hydroxy-trans-stilbene + H2O2
4,4'-dihydroxy-trans-stilbene + H2O
-
-
-
?
4-hydroxy-trans-stilbene + H2O2
4,4'-dihydroxy-trans-stilbene + H2O
-
-
-
?
4-nitrobenzaldehyde + H2O2
4-nitrobenzoic acid + H2O
-
-
-
-
?
4-nitrobenzaldehyde + H2O2
4-nitrobenzoic acid + H2O
-
-
-
-
?
4-nitrobenzaldehyde + H2O2
4-nitrobenzoic acid + H2O
-
-
-
?
4-nitrobenzaldehyde + H2O2
4-nitrobenzoic acid + H2O
-
-
-
-
?
4-nitrobenzaldehyde + H2O2
4-nitrobenzoic acid + H2O
-
-
-
-
?
4-nitrobenzaldehyde + H2O2
4-nitrobenzoic acid + H2O
-
-
-
?
4-nitrobenzaldehyde + H2O2
4-nitrobenzoic acid + H2O
-
-
-
-
?
4-nitrobenzaldehyde + H2O2
4-nitrobenzoic acid + H2O
-
-
-
-
?
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-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-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-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-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-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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
5-bromoindole + 5-bromoindoline + H2O2
5,5'-dibromoindigo + H2O
-
-
-
-
?
5-bromoindole + 5-bromoindoline + H2O2
5,5'-dibromoindigo + H2O
-
-
-
-
?
5-bromoindole + 5-bromoindoline + H2O2
5,5'-dibromoindigo + H2O
-
-
-
-
?
5-hydroxymethylfurfural + H2O2
2,5-furandicarboxylic acid + H2O
-
-
-
-
?
5-hydroxymethylfurfural + H2O2
2,5-furandicarboxylic acid + H2O
-
-
-
-
?
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + formic acid + H2O
-
-
-
?
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + formic acid + H2O
-
-
-
?
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + formic acid + H2O
-
-
-
-
?
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + formic acid + H2O
-
-
-
-
?
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + formic acid + H2O
-
-
-
?
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + formic acid + H2O
-
-
-
?
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + formic acid + H2O
-
-
-
-
?
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + H2O
-
-
-
-
?
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + H2O
-
-
-
-
?
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + H2O
-
-
-
-
?
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + H2O
-
-
-
-
?
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + H2O
-
-
-
?
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + H2O
-
-
-
?
5-nitro-1,3-benzodioxole + H2O2
4-nitrocatechol + H2O
-
-
-
-
?
5-nitro-1,3-benzodioxole + H2O2
?
-
-
-
-
?
5-nitro-1,3-benzodioxole + H2O2
?
-
-
-
-
?
6-bromoindole + H2O2
6-bromo-2-oxindole + 3-oxo-6-bromoindole + H2O
-
-
-
-
?
6-bromoindole + H2O2
6-bromo-2-oxindole + 3-oxo-6-bromoindole + H2O
-
-
-
-
?
6-bromoindole + H2O2
6-bromo-2-oxindole + 3-oxo-6-bromoindole + H2O
-
-
-
-
?
7,11-epoxymegastigma-5(6)-en-9-one + H2O2
4-hydroxy-7,11-epoxymegastigma-5(6)-en-9-one + H2O
-
-
-
-
?
7,11-epoxymegastigma-5(6)-en-9-one + H2O2
4-hydroxy-7,11-epoxymegastigma-5(6)-en-9-one + H2O
-
-
-
-
?
7,11-epoxymegastigma-5(6)-en-9-one + H2O2
4-hydroxy-7,11-epoxymegastigma-5(6)-en-9-one + H2O
-
-
-
-
?
7,11-epoxymegastigma-5(6)-en-9-one + H2O2
4-hydroxy-7,11-epoxymegastigma-5(6)-en-9-one + H2O
-
-
-
-
?
7,11-epoxymegastigma-5(6)-en-9-one + H2O2
4-hydroxy-7,11-epoxymegastigma-5(6)-en-9-one + H2O
-
-
-
-
?
7,11-epoxymegastigma-5(6)-en-9-one + H2O2
4-hydroxy-7,11-epoxymegastigma-5(6)-en-9-one + H2O
-
-
-
-
?
acetanilide + H2O2
paracetamol + H2O
-
-
-
-
?
acetanilide + H2O2
paracetamol + H2O
-
-
-
?
acetanilide + H2O2
paracetamol + H2O
-
-
-
-
?
alpha-damascone + H2O2
3-hydroxy-alpha-damascone + 10-hydroxy-alpha-damascone + 4-epoxy-alpha-damascone + H2O
-
-
-
-
?
alpha-damascone + H2O2
3-hydroxy-alpha-damascone + 10-hydroxy-alpha-damascone + 4-epoxy-alpha-damascone + H2O
-
-
-
-
?
alpha-damascone + H2O2
3-hydroxy-alpha-damascone + 10-hydroxy-alpha-damascone + 4-epoxy-alpha-damascone + H2O
-
-
-
-
?
alpha-damascone + H2O2
3-hydroxy-alpha-damascone + 10-hydroxy-alpha-damascone + 4-epoxy-alpha-damascone + H2O
-
-
-
-
?
alpha-damascone + H2O2
3-hydroxy-alpha-damascone + 10-hydroxy-alpha-damascone + 4-epoxy-alpha-damascone + H2O
-
-
-
-
?
alpha-damascone + H2O2
3-hydroxy-alpha-damascone + 10-hydroxy-alpha-damascone + 4-epoxy-alpha-damascone + H2O
-
-
-
-
?
alpha-ionone + H2O2
3-hydroxy-alpha-ionone + 4-epoxy-alpha-ionone + H2O
-
i.e. rac-(3E)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
-
-
?
alpha-ionone + H2O2
3-hydroxy-alpha-ionone + 4-epoxy-alpha-ionone + H2O
-
i.e. rac-(3E)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
-
-
?
alpha-ionone + H2O2
3-hydroxy-alpha-ionone + 4-epoxy-alpha-ionone + H2O
-
i.e. rac-(3E)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
-
-
?
alpha-ionone + H2O2
3-hydroxy-alpha-ionone + 4-epoxy-alpha-ionone + H2O
-
i.e. rac-(3E)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
-
-
?
alpha-ionone + H2O2
3-hydroxy-alpha-ionone + 4-epoxy-alpha-ionone + H2O
-
i.e. rac-(3E)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
-
-
?
alpha-ionone + H2O2
3-hydroxy-alpha-ionone + 4-epoxy-alpha-ionone + H2O
-
i.e. rac-(3E)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
-
-
?
anthracene + H2O2
mono-hydroxylated anthracene + dihydroxylated anthracene
-
-
-
-
?
anthracene + H2O2
mono-hydroxylated anthracene + dihydroxylated anthracene
-
the enzyme almost completely converts anthracene within 6 h
-
-
?
benzene + H2O2
phenol + H2O
-
-
-
-
?
benzene + H2O2
phenol + H2O
-
-
-
?
benzene + H2O2
phenol + H2O
-
oxygenation of the unactivated aromatic ring of benzene with hydrogen peroxide as co-substrate. Reaction proceeds via an initial epoxide intermediate that re-aromatizes in aqueous solution to form phenol. Second and third [per]oxygenation is also observed and results in the formation of further hydroxylation and following [per]oxidation products hydroquinone and p-benzoquinone, catechol and o-benzoquinone as well as 1,2,4-trihydroxybenzene and hydroxy-p-benzoquinone, respectively. The origin of the oxygen atom incorporated into benzene or phenol is the peroxide
-
?
benzene + H2O2
phenol + H2O
-
-
-
-
?
benzyl alcohol + H2O2
benzaldehyde + H2O
-
-
-
-
?
benzyl alcohol + H2O2
benzaldehyde + H2O
-
-
-
-
?
benzyl alcohol + H2O2
benzaldehyde + H2O
-
-
-
-
?
benzyl alcohol + H2O2
benzaldehyde + H2O
-
-
-
-
?
benzyl alcohol + H2O2
benzaldehyde + H2O
-
-
-
?
benzyl alcohol + H2O2
benzaldehyde + H2O
-
-
-
-
?
benzyl alcohol + H2O2
benzaldehyde + H2O
-
-
-
?
benzyl alcohol + H2O2
benzaldehyde + H2O
-
-
-
-
?
beta-damascone + H2O2
4-hydroxy-beta-damascone + 10-hydroxy-beta-damascone + 3-hydroxy-beta-damascone + H2O
-
-
-
-
?
beta-damascone + H2O2
4-hydroxy-beta-damascone + 10-hydroxy-beta-damascone + 3-hydroxy-beta-damascone + H2O
-
-
-
-
?
beta-damascone + H2O2
4-hydroxy-beta-damascone + 10-hydroxy-beta-damascone + 3-hydroxy-beta-damascone + H2O
-
-
-
-
?
beta-damascone + H2O2
4-hydroxy-beta-damascone + 10-hydroxy-beta-damascone + 3-hydroxy-beta-damascone + H2O
-
-
-
-
?
beta-damascone + H2O2
4-hydroxy-beta-damascone + 10-hydroxy-beta-damascone + 3-hydroxy-beta-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
-
i.e. rac-(3E)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
-
-
?
beta-ionone + H2O2
4-hydroxy-beta-ionone + 3-hydroxy-beta-ionone + 2-hydroxy-beta-ionone + 13-hydroxy-beta-ionone + 10-hydroxy-beta-ionone + H2O
-
i.e. rac-(3E)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
-
-
?
beta-ionone + H2O2
4-hydroxy-beta-ionone + 3-hydroxy-beta-ionone + 2-hydroxy-beta-ionone + 13-hydroxy-beta-ionone + 10-hydroxy-beta-ionone + H2O
-
i.e. rac-(3E)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
-
-
?
beta-ionone + H2O2
4-hydroxy-beta-ionone + 3-hydroxy-beta-ionone + 2-hydroxy-beta-ionone + 13-hydroxy-beta-ionone + 10-hydroxy-beta-ionone + H2O
-
i.e. rac-(3E)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
-
-
?
beta-ionone + H2O2
4-hydroxy-beta-ionone + 3-hydroxy-beta-ionone + 2-hydroxy-beta-ionone + 13-hydroxy-beta-ionone + 10-hydroxy-beta-ionone + H2O
-
i.e. rac-(3E)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
-
-
?
beta-ionone + H2O2
4-hydroxy-beta-ionone + 3-hydroxy-beta-ionone + 2-hydroxy-beta-ionone + 13-hydroxy-beta-ionone + 10-hydroxy-beta-ionone + H2O
-
i.e. rac-(3E)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
-
-
?
carbamazepine + H2O2
3-hydroxycarbamazepine + H2O
-
-
-
-
?
carbamazepine + H2O2
3-hydroxycarbamazepine + H2O
-
-
-
?
carbamazepine + H2O2
3-hydroxycarbamazepine + H2O
-
-
-
-
?
cholecalciferol + H2O2
25-hydroxycholecalciferol + 24-hydroxycholecalciferol + 26,27-hydroxycholecalciferol + H2O
-
-
-
-
?
cholecalciferol + H2O2
25-hydroxycholecalciferol + 24-hydroxycholecalciferol + 26,27-hydroxycholecalciferol + H2O
-
-
-
-
?
cortisone + H2O2
cortisone 21-gem-diol + cortisone 21-oic acid + adrenosterone + H2O
-
-
-
?
cortisone + H2O2
cortisone 21-gem-diol + cortisone 21-oic acid + adrenosterone + H2O
-
-
-
-
?
cortisone + H2O2
cortisone 21-gem-diol + cortisone 21-oic acid + adrenosterone + H2O
-
-
-
-
?
cortisone 21-al + H2O2
cortisone 21-oic acid + H2O
-
-
-
?
cortisone 21-al + H2O2
cortisone 21-oic acid + H2O
-
-
-
-
?
cortisone 21-al + H2O2
cortisone 21-oic acid + H2O
-
-
-
-
?
cyclohexane + H2O2
cyclohexanol + H2O
-
-
-
-
?
cyclohexane + H2O2
cyclohexanol + H2O
-
-
-
-
?
cyclohexane + H2O2
cyclohexanol + H2O
-
-
-
?
cyclohexane + H2O2
cyclohexanol + H2O
-
-
-
-
?
cyclohexanol + H2O2
cyclohexanone + H2O
-
-
-
-
?
cyclohexanol + H2O2
cyclohexanone + H2O
-
-
-
-
?
cyclohexanol + H2O2
cyclohexanone + H2O
-
-
-
?
cyclohexanol + H2O2
cyclohexanone + H2O
-
-
-
-
?
daidzein + H2O2
6-hydroxydaidzein + H2O
-
-
-
-
?
daidzein + H2O2
6-hydroxydaidzein + H2O
-
-
-
?
daidzein + H2O2
6-hydroxydaidzein + H2O
-
-
-
-
?
dibenzofuran + H2O2
3-hydroxy-dibenzofuran + monohydroxylated dibenzofuran + 2,3-dihydroxydibenzofuran + 3,7-dihydroxydibenzofuran + dihydroxylated dibenzofuran + trihydroxylated dibenzofuran + H2O
-
-
-
-
?
dibenzofuran + H2O2
3-hydroxy-dibenzofuran + monohydroxylated dibenzofuran + 2,3-dihydroxydibenzofuran + 3,7-dihydroxydibenzofuran + dihydroxylated dibenzofuran + trihydroxylated dibenzofuran + H2O
-
-
-
-
?
dibenzothiophene + H2O2
?
-
in vivo Coprinellus radians peroxygenase converts about 60% of dibenzothiophene into dibenzothiophene sulfoxide and dibenzothiophene sulfone as the sole metabolites. In vitro a total of seven oxygenation products are detected after dibenzothiophene conversion by the purified peroxygenase with dibenzothiophene sulfoxide as major product
-
-
?
dibenzothiophene + H2O2
?
-
in vivo Agrocybe aegerita peroxygenase oxidizes dibenzothiophene (0.11 mM) by 100% within 16 days into eight different metabolites. Among the latter are mainly S-oxidation products (dibenzothiophene sulfoxide, dibenzothiophene sulfone) and in lower amounts ring-hydroxylation compounds (e.g., 2-hydroxy-dibenzothiophene). In vitro a total of 19 oxygenation products are detected after dibenzothiophene conversion by the purified peroxygenase with ring hydroxylation favored over S-oxidation with 2-hydroxy-dibenzothiophene as major product
-
-
?
diclofenac + H2O2
4'-hydroxydiclofenac + H2O
-
-
-
-
?
diclofenac + H2O2
4'-hydroxydiclofenac + H2O
-
-
-
?
diclofenac + H2O2
4'-hydroxydiclofenac + H2O
-
-
-
-
?
diethyl ether + H2O2
ethanol + acetaldehyde + H2O
-
-
-
-
?
diethyl ether + H2O2
ethanol + acetaldehyde + H2O
-
-
-
?
diethyl ether + H2O2
ethanol + acetaldehyde + H2O
-
-
-
-
?
docosa-4,7,10,13,16,19-hexaenoic acid + H2O2
19,20-epoxydocosa-4,7,10,13,16-pentaenoic acid + H2O
-
more than 99% conversion
-
-
?
docosa-4,7,10,13,16,19-hexaenoic acid + H2O2
19,20-epoxydocosa-4,7,10,13,16-pentaenoic acid + H2O
-
more than 99% conversion
-
-
?
docosa-7,10,13,16,19-pentaenoic acid + H2O2
19,20-epoxydocosa-7,10,13,16-tetraenoic acid + H2O
-
more than 99% conversion
-
-
?
docosa-7,10,13,16,19-pentaenoic acid + H2O2
19,20-epoxydocosa-7,10,13,16-tetraenoic acid + H2O
-
more than 99% conversion
-
-
?
eicosa-11,14,17-trienoic acid + H2O2
17,18-epoxyeicosa-11,14-dienoic acid + H2O
-
more than 99% conversion
-
-
?
eicosa-11,14,17-trienoic acid + H2O2
17,18-epoxyeicosa-11,14-dienoic acid + H2O
-
more than 99% conversion
-
-
?
eicosa-5,8,11,14,17-pentaenoic acid + H2O2
17,18-epoxyeicosa-5,8,11,14-tetraenoic acid + H2O
-
more than 99% conversion
-
-
?
eicosa-5,8,11,14,17-pentaenoic acid + H2O2
17,18-epoxyeicosa-5,8,11,14-tetraenoic acid + H2O
-
more than 99% conversion
-
-
?
ergocalciferol + H2O2
25-hydroxyergocalciferol + H2O
-
-
-
-
?
ergocalciferol + H2O2
25-hydroxyergocalciferol + H2O
-
-
-
-
?
erucic acid + H2O2
? + H2O
-
-
-
-
?
erucic acid + H2O2
? + H2O
-
-
-
-
?
ethylbenzene + H2O2
(R)-phenylethanol + H2O
-
-
-
-
?
ethylbenzene + H2O2
(R)-phenylethanol + H2O
-
-
-
?
ethylbenzene + H2O2
(R)-phenylethanol + H2O
-
-
-
-
?
ethylbenzene + H2O2
1-phenylethanol + H2O
-
-
-
?
ethylbenzene + H2O2
1-phenylethanol + H2O
-
-
1-phenylethanol is the major product
-
?
ethylbenzene + H2O2
1-phenylethanol + H2O
-
-
1-phenylethanol is the major product
-
?
ethylbenzene + H2O2
1-phenylethanol + H2O
-
-
-
?
flavone + H2O2
6-hydroxyflavone + H2O
-
-
-
-
?
flavone + H2O2
6-hydroxyflavone + H2O
-
-
-
?
flavone + H2O2
6-hydroxyflavone + H2O
-
-
-
-
?
fluorene + H2O2
?
-
-
-
?
fluorene + H2O2
?
-
-
-
-
?
heneicosa-6,9,12,15,18-pentaenoic acid + H2O2
18,19-epoxyheneicosa-6,9,12,15-tetraenoic acid + H2O
-
more than 99% conversion
-
-
?
heneicosa-6,9,12,15,18-pentaenoic acid + H2O2
18,19-epoxyheneicosa-6,9,12,15-tetraenoic acid + H2O
-
more than 99% conversion
-
-
?
indole + H2O2
2-oxindole + indoxyl + H2O
-
-
-
-
?
indole + H2O2
2-oxindole + indoxyl + H2O
-
-
-
-
?
indole + H2O2
2-oxindole + indoxyl + H2O
-
-
-
-
?
indoline + H2O2
3-hydroxyindoline + H2O
-
-
-
-
?
indoline + H2O2
3-hydroxyindoline + H2O
-
-
-
-
?
indoline + H2O2
3-hydroxyindoline + H2O
-
-
-
-
?
isophorone + H2O2
(S)-4-hydroxyisophorone + 7-hydroxyisophorone + 7-formylisophorone + 4-ketoisophorone + H2O
72% conversion, reaction with 0.0001 mM enzyme and 5 mM H2O2
-
-
?
isophorone + H2O2
(S)-4-hydroxyisophorone + 7-hydroxyisophorone + 7-formylisophorone + 4-ketoisophorone + H2O
96% conversion, reaction with 0.00025 mM enzyme and 5 mM H2O2
-
-
?
isophorone + H2O2
(S)-4-hydroxyisophorone + 7-hydroxyisophorone + 7-formylisophorone + 4-ketoisophorone + H2O
72% conversion, reaction with 0.0001 mM enzyme and 5 mM H2O2
-
-
?
isophorone + H2O2
(S)-4-hydroxyisophorone + 7-hydroxyisophorone + 7-formylisophorone + 4-ketoisophorone + H2O
96% conversion, reaction with 0.00025 mM enzyme and 5 mM H2O2
-
-
?
isophorone + H2O2
4-hydroxyisophorone + 4-ketoisophorone + H2O
-
95% conversion, reaction with 0.0001 mM enzyme and 2.5 mM H2O2
-
-
?
isophorone + H2O2
4-hydroxyisophorone + 4-ketoisophorone + H2O
-
95% conversion, reaction with 0.0001 mM enzyme and 2.5 mM H2O2
-
-
?
isophorone + H2O2
4-hydroxyisophorone + 4-ketoisophorone + H2O
-
100% conversion, reaction with 0.0005 mM enzyme and 5 mM H2O2
-
-
?
isophorone + H2O2
4-ketoisophorone + H2O
-
100% conversion, reaction with 0.0005 mM enzyme and 5 mM H2O2
-
-
?
isophorone + H2O2
4-ketoisophorone + H2O
-
100% conversion, reaction with 0.0005 mM enzyme and 5 mM H2O2
-
-
?
lauric acid + H2O2
omega-1-hydroxylauric acid + omega-2-hydroxylauric acid + omega-hydroxylauric acid + H2O
-
-
-
-
?
lauric acid + H2O2
omega-1-hydroxylauric acid + omega-2-hydroxylauric acid + omega-hydroxylauric acid + H2O
-
-
-
?
lauric acid + H2O2
omega-1-hydroxylauric acid + omega-2-hydroxylauric acid + omega-hydroxylauric acid + H2O
-
-
-
-
?
lidocaine + H2O2
monoglycinexylidede + glycinexylidide + H2O
-
-
-
-
?
lidocaine + H2O2
monoglycinexylidede + glycinexylidide + H2O
-
-
-
?
lidocaine + H2O2
monoglycinexylidede + glycinexylidide + H2O
-
-
-
-
?
linoleic acid + H2O2
? + H2O
-
-
-
-
?
linoleic acid + H2O2
? + H2O
-
-
-
-
?
linoleic acid methyl ester + H2O2
? + H2O
-
-
-
-
?
linoleic acid methyl ester + H2O2
? + H2O
-
-
-
-
?
methyl benzoate + H2O2
?
-
-
-
-
?
methyl benzoate + H2O2
?
-
-
-
?
methyl benzoate + H2O2
?
-
-
-
-
?
myristoleic acid + H2O2
? + H2O
-
-
-
-
?
myristoleic acid + H2O2
? + H2O
-
-
-
-
?
n-heptane + H2O2
2-heptanol + 3-heptanol + H2O
-
-
-
-
?
n-heptane + H2O2
2-heptanol + 3-heptanol + H2O
-
-
-
?
n-heptane + H2O2
2-heptanol + 3-heptanol + H2O
-
-
-
-
?
N-phthaloyl-phenethylamine + H2O2
2-(2-hydroxy-2-phenylethyl)-1H-isoindole-1,3(2H)-dione + H2O
-
-
-
-
?
N-phthaloyl-phenethylamine + H2O2
2-(2-hydroxy-2-phenylethyl)-1H-isoindole-1,3(2H)-dione + H2O
-
-
-
-
?
N-phthaloyl-phenethylamine + H2O2
2-(2-hydroxy-2-phenylethyl)-1H-isoindole-1,3(2H)-dione + H2O
-
-
-
-
?
N-phthaloyl-phenethylamine + H2O2
2-(2-hydroxy-2-phenylethyl)-1H-isoindole-1,3(2H)-dione + H2O
-
-
-
-
?
N-phthaloyl-phenethylamine + H2O2
2-(2-hydroxy-2-phenylethyl)-1H-isoindole-1,3(2H)-dione + H2O
-
-
-
-
?
N-phthaloyl-phenethylamine + H2O2
2-(2-hydroxy-2-phenylethyl)-1H-isoindole-1,3(2H)-dione + H2O
-
-
-
-
?
N-phthaloyl-phenethylamine + H2O2
2-(2-hydroxy-2-phenylethyl)-1H-isoindole-1,3(2H)-dione + H2O
-
-
-
-
?
naphthalene + H2O2
1-naphthol + H2O
-
-
-
-
?
naphthalene + H2O2
1-naphthol + H2O
-
-
-
-
?
naphthalene + H2O2
1-naphthol + H2O
-
-
-
?
naphthalene + H2O2
1-naphthol + H2O
-
-
-
?
naphthalene + H2O2
1-naphthol + H2O
-
-
-
-
?
naphthalene + H2O2
1-naphthol + H2O
-
-
-
-
?
naphthalene + H2O2
1-naphthol + H2O
-
-
-
?
naphthalene + H2O2
1-naphthol + H2O
-
-
in addition to 1-naphthol a smaller amount of naphthalene is converted to 2 naphthol dependent on pH, at pH 7.0-8.0 3% 2-naphthol and 97% 1-naphthol are formed while at pH 3.0 18% 2-naphthol and 82% 1-naphthol are formed. Traces of 1-naphthol are later oxidized to 1,4-naphthoquinone
-
?
naphthalene + H2O2
1-naphthol + H2O
-
-
-
-
?
naphthalene + H2O2
1-naphthol + H2O
-
-
-
?
naphthalene + H2O2
1-naphthol + H2O
-
-
-
-
?
naphthalene + H2O2
?
-
-
-
-
?
naphthalene + H2O2
?
-
-
-
-
?
naphthalene + H2O2
?
-
-
-
-
?
naphthalene + H2O2
?
-
-
-
?
naphthalene + H2O2
naphthalene 1,2-oxide + H2O
-
-
-
-
?
naphthalene + H2O2
naphthalene 1,2-oxide + H2O
-
the enzyme selectively hydroxylates the aromatic ring of naphthalene
naphthalene 1,2-oxide is the primary product of Agrocybe aegerita peroxidase/peroxygenase-catalyzed oxygenation of naphthalene
-
?
naphthalene + H2O2
naphthol + 1,4-naphthoquinone + H2O
-
-
-
-
?
naphthalene + H2O2
naphthol + 1,4-naphthoquinone + H2O
-
-
-
-
?
naphthalene + H2O2
naphthol + 1,4-naphthoquinone + H2O
-
-
-
-
?
naphthalene + H2O2
naphthol + 1,4-naphthoquinone + H2O
-
-
-
-
?
naphthalene + H2O2
naphthol + 1,4-naphthoquinone + H2O
-
-
-
-
?
naphthalene + H2O2
naphthol + 1,4-naphthoquinone + H2O
-
-
-
-
?
naphthalene + H2O2
naphthol + 1,4-naphthoquinone + H2O
-
-
-
-
?
oleic acid + H2O2
? + H2O
-
-
-
-
?
oleic acid + H2O2
? + H2O
-
-
-
-
?
palmitoleic acid + H2O2
? + H2O
-
-
-
-
?
palmitoleic acid + H2O2
? + H2O
-
-
-
-
?
phenol + H2O2
hydroquinone + catechol + H2O
-
-
-
-
?
phenol + H2O2
hydroquinone + catechol + H2O
-
-
-
?
phenol + H2O2
hydroquinone + catechol + H2O
-
-
-
-
?
phenylbutane + H2O2
1-phenylbutan-1-ol + H2O
-
-
-
-
?
phenylbutane + H2O2
1-phenylbutan-1-ol + H2O
-
-
-
-
?
phenylbutane + H2O2
1-phenylbutan-1-ol + H2O
-
-
-
-
?
phenylbutane + H2O2
1-phenylbutan-1-ol + H2O
-
-
-
-
?
phenylbutane + H2O2
1-phenylbutan-1-ol + H2O
-
-
-
-
?
phenylbutane + H2O2
1-phenylbutan-1-ol + H2O
-
-
-
-
?
phenylbutane + H2O2
1-phenylbutan-1-ol + H2O
-
-
-
-
?
phenylethane + H2O2
1-phenylethan-1-ol + H2O
-
-
-
-
?
phenylethane + H2O2
1-phenylethan-1-ol + H2O
-
-
-
-
?
phenylethane + H2O2
1-phenylethan-1-ol + H2O
-
-
-
-
?
phenylethane + H2O2
1-phenylethan-1-ol + H2O
-
-
-
-
?
phenylethane + H2O2
1-phenylethan-1-ol + H2O
-
-
-
-
?
phenylethane + H2O2
1-phenylethan-1-ol + H2O
-
-
-
-
?
phenylethane + H2O2
1-phenylethan-1-ol + H2O
-
-
-
-
?
phenylpentane + H2O2
1-phenylpentan-1-ol + H2O
-
-
-
-
?
phenylpentane + H2O2
1-phenylpentan-1-ol + H2O
-
-
-
-
?
phenylpentane + H2O2
1-phenylpentan-1-ol + H2O
-
-
-
-
?
phenylpentane + H2O2
1-phenylpentan-1-ol + H2O
-
-
-
-
?
phenylpentane + H2O2
1-phenylpentan-1-ol + H2O
-
-
-
-
?
phenylpentane + H2O2
1-phenylpentan-1-ol + H2O
-
-
-
-
?
phenylpentane + H2O2
1-phenylpentan-1-ol + H2O
-
-
-
-
?
phenylpropane + H2O2
1-phenylpropan-1-ol + H2O
-
-
-
-
?
phenylpropane + H2O2
1-phenylpropan-1-ol + H2O
-
-
-
-
?
phenylpropane + H2O2
1-phenylpropan-1-ol + H2O
-
-
-
-
?
phenylpropane + H2O2
1-phenylpropan-1-ol + H2O
-
-
-
-
?
phenylpropane + H2O2
1-phenylpropan-1-ol + H2O
-
-
-
-
?
phenylpropane + H2O2
1-phenylpropan-1-ol + H2O
-
-
-
-
?
phenylpropane + H2O2
1-phenylpropan-1-ol + H2O
-
-
-
-
?
prednisone + H2O2
? + H2O
-
-
-
?
prednisone + H2O2
? + H2O
-
-
-
-
?
propane + H2O2
isopropanol + H2O
-
-
-
-
?
propane + H2O2
isopropanol + H2O
-
-
-
?
propane + H2O2
isopropanol + H2O
-
-
-
-
?
propranolol + H2O2
5-hydroxypropranolol + H2O
-
-
-
-
?
propranolol + H2O2
5-hydroxypropranolol + H2O
-
-
-
?
propranolol + H2O2
5-hydroxypropranolol + H2O
-
-
-
-
?
pyrene + H2O2
1-pyrenol + H2O
-
13% of pyrene is oxidized within 8 h
-
-
?
pyrene + H2O2
1-pyrenol + H2O
-
45% of pyrene is oxidized within 8 h
-
-
?
pyridine + H2O2
pyridine N-oxide + H2O
-
-
-
-
?
pyridine + H2O2
pyridine N-oxide + H2O
-
-
-
-
?
pyridine + H2O2
pyridine N-oxide + H2O
-
-
-
?
pyridine + H2O2
pyridine N-oxide + H2O
-
100% conversion
-
-
?
pyridine + H2O2
pyridine N-oxide + H2O
-
-
-
-
?
resveratrol + H2O2
oxyresveratrol + H2O
-
-
-
-
?
resveratrol + H2O2
oxyresveratrol + H2O
-
-
-
?
sildenafil + H2O2
N-desmethylsildenafil + formaldehyde + H2O
-
-
-
-
?
sildenafil + H2O2
N-desmethylsildenafil + formaldehyde + H2O
-
-
-
?
sildenafil + H2O2
N-desmethylsildenafil + formaldehyde + H2O
-
-
-
-
?
styrene + H2O2
styrene oxide + H2O
-
-
-
-
?
styrene + H2O2
styrene oxide + H2O
-
-
-
-
?
styrene + H2O2
styrene oxide + H2O
-
-
-
-
?
styrene + H2O2
styrene oxide + H2O
-
-
-
-
?
styrene + H2O2
styrene oxide + H2O
-
-
-
-
?
styrene + H2O2
styrene oxide + H2O
-
-
-
-
?
styrene + H2O2
styrene oxide + H2O
-
-
-
-
?
tetrahydrofuran + H2O2
4-hydroxybutanal + H2O
-
-
-
-
?
tetrahydrofuran + H2O2
4-hydroxybutanal + H2O
-
-
-
-
?
tetrahydrofuran + H2O2
4-hydroxybutanal + H2O
-
-
-
?
tetrahydrofuran + H2O2
4-hydroxybutanal + H2O
-
-
-
-
?
toluene + H2O2
benzyl alcohol + H2O
-
-
-
-
?
toluene + H2O2
benzyl alcohol + H2O
-
the initial product of toluene oxidation is benzyl alcohol, which then declines with concomitant production of benzaldehyde, which in turn declines with concomitant production of benzoic acid. The reactions proceed stepwise with total conversions of 93% for toluene
-
-
?
toluene + H2O2
o-cresol + p-cresol + H2O
-
-
-
-
?
toluene + H2O2
o-cresol + p-cresol + H2O
-
-
-
?
toluene + H2O2
o-cresol + p-cresol + H2O
-
-
-
-
?
trans-stilbene + H2O2
4,4'-dihydroxy-trans-stilbene + tri-hydroxylated trans-stilbene + H2O
-
-
-
-
?
trans-stilbene + H2O2
4,4'-dihydroxy-trans-stilbene + tri-hydroxylated trans-stilbene + H2O
-
-
-
?
trans-stilbene + H2O2
4,4'-dihydroxy-trans-stilbene + tri-hydroxylated trans-stilbene + H2O
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
-
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
-
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
-
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
-
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
-
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
-
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
-
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
-
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
-
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
-
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
-
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
-
-
-
-
?
veratryl alcohol + H2O2
veratraldehyde + H2O
-
-
-
-
?
veratryl alcohol + H2O2 + H+
veratraldehyde + H2O
-
-
-
-
?
veratryl alcohol + H2O2 + H+
veratraldehyde + H2O
-
-
-
-
?
veratryl alcohol + H2O2 + H+
veratraldehyde + H2O
-
-
-
?
veratryl alcohol + H2O2 + H+
veratraldehyde + H2O
-
-
-
-
?
additional information
?
-
the enzyme is not capable of oxidizing bromide or chloride
-
-
?
additional information
?
-
-
the enzyme is not capable of oxidizing bromide or chloride
-
-
?
additional information
?
-
-
no activity with pinosylvin and resveratrol
-
-
-
additional information
?
-
the enzyme is not capable of oxidizing bromide or chloride
-
-
?
additional information
?
-
-
the enzyme also brominates phenol to 2- and 4-bromophenols and selectively hydroxylates naphthalene to 1-naphthol, but shows no laccase activity
-
-
?
additional information
?
-
-
the enzyme does not oxidize phenanthrene and perylene
-
-
?
additional information
?
-
-
regioselective hydroxylation of saturated/unsaturated fatty acids is observed at the omega-1 and omega-2 position, but only at the omega-2 position in myristoleic acid. Alkyl esters of fatty acids and monoglycerides are also omga-1 or omega-2 hydroxylated, but di- and tri-glycerides are not modified. Fatty alcohols yield hydroxy derivatives at the omega-1 or omega-2 positions (diols) but also fatty acids and their hydroxy derivatives. The peroxygenase is able to oxyfunctionalize alkanes giving, in addition to alcohols at positions 2 or 3, dihydroxylated derivatives at both sides of the molecule. The predominance of mono- or di-hydroxylated derivatives seems related to the higher or lower proportion of acetone, respectively, in the reaction medium
-
-
?
additional information
?
-
-
the enzyme fails to transform isophorone
-
-
-
additional information
?
-
-
nicotinic acid, nicotine amide, 3,5-dichloropyridine and perchloropyridine are no substrates
-
-
?
additional information
?
-
-
the Agrocybe aegerita peroxidase has strong brominating as well as weak chlorinating and iodating activities, and catalyzes both benzylic and aromatic hydroxylations
-
-
?
additional information
?
-
-
the enzyme does not oxidize perylene
-
-
?
additional information
?
-
-
the enzyme exhibits also haloperoxidase activity as shown by the chlorination or bromination of monochlorodimedone. Ethanol is not oxidized by the peroxidase
-
-
?
additional information
?
-
-
the enzyme fails to cleave a 4-nitrophenyl-terminated polyethylene glycol
-
-
?
additional information
?
-
-
the transferred oxygen exclusively originates from the peroxide. Benzylic hydroxylation leads exclusively to the (R)-1-phenylalkanols. For (R)-1-phenylethanol, (R)-1-phenylpropanol and (R)-1-tetralol, the enantiomeric excess reaches >99%. For longer chain lengths, the enantiomeric excesses and total turnover numbers decrease while the number of by-products, e.g. 1-phenylketones, increase
-
-
?
additional information
?
-
benzyloxyacetate is not a substrate
-
-
-
additional information
?
-
the enzyme shows no activity with cortisone and negligible oxidation of prednisone and 11-deoxycortisol
-
-
-
additional information
?
-
-
enzyme shows neither brominating nor chlorinating activities
-
-
?
additional information
?
-
the enzyme fails to transform isophorone
-
-
-
additional information
?
-
the enzyme fails to transform isophorone
-
-
-
additional information
?
-
the enzyme catalyzes hydrogen peroxide-driven ethylbenzene hydroxylation, as well as styrene epoxidation. The ethylbenzene hydroxylation activity is higher than the styrene epoxidation activity, maybe due to a difference in the binding affinity of the two substrates. The rate-limiting steps of ethylbenzene hydroxylation and styrene epoxidation are the same, and may be any step before formation of the active oxidant
-
-
?
additional information
?
-
the enzyme catalyzes hydrogen peroxide-driven ethylbenzene hydroxylation, as well as styrene epoxidation. The ethylbenzene hydroxylation activity is higher than the styrene epoxidation activity, maybe due to a difference in the binding affinity of the two substrates. The rate-limiting steps of ethylbenzene hydroxylation and styrene epoxidation are the same, and may be any step before formation of the active oxidant
-
-
?
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Hofrichter, M.; Ullrich, R.
Heme-thiolate haloperoxidases: versatile biocatalysts with biotechnological and environmental significance
Appl. Microbiol. Biotechnol.
71
276-288
2006
Cyclocybe aegerita
brenda
Piontek, K.; Ullrich, R.; Liers, C.; Diederichs, K.; Plattner, D.A.; Hofrichter, M.
Crystallization of a 45 kDa peroxygenase/peroxidase from the mushroom Agrocybe aegerita and structure determination by SAD utilizing only the haem iron
Acta Crystallogr. Sect. F
66
693-698
2010
Cyclocybe aegerita
brenda
Ullrich, R.; Nuske, J.; Scheibner, K.; Spantzel, J.; Hofrichter, M.
Novel haloperoxidase from the agaric basidiomycete Agrocybe aegerita oxidizes aryl alcohols and aldehydes
Appl. Environ. Microbiol.
70
4575-4581
2004
Cyclocybe aegerita
brenda
Anh, D.H.; Ullrich, R.; Benndorf, D.; Svatos, A.; Muck, A.; Hofrichter, M.
The coprophilous mushroom Coprinus radians secretes a haloperoxidase that catalyzes aromatic peroxygenation
Appl. Environ. Microbiol.
73
5477-5485
2007
Coprinellus radians
brenda
Kluge, M.G.; Ullrich, R.; Scheibner, K.; Hofrichter, M.
Spectrophotometric assay for detection of aromatic hydroxylation catalyzed by fungal haloperoxidase-peroxygenase
Appl. Microbiol. Biotechnol.
75
1473-1478
2007
Cyclocybe aegerita
brenda
Kluge, M.; Ullrich, R.; Dolge, C.; Scheibner, K.; Hofrichter, M.
Hydroxylation of naphthalene by aromatic peroxygenase from Agrocybe aegerita proceeds via oxygen transfer from H2O2 and intermediary epoxidation
Appl. Microbiol. Biotechnol.
81
1071-1076
2009
Cyclocybe aegerita
brenda
Aranda, E.; Kinne, M.; Kluge, M.; Ullrich, R.; Hofrichter, M.
Conversion of dibenzothiophene by the mushrooms Agrocybe aegerita and Coprinellus radians and their extracellular peroxygenases
Appl. Microbiol. Biotechnol.
82
1057-1066
2009
Cyclocybe aegerita, Coprinellus radians
brenda
Pecyna, M.J.; Ullrich, R.; Bittner, B.; Clemens, A.; Scheibner, K.; Schubert, R.; Hofrichter, M.
Molecular characterization of aromatic peroxygenase from Agrocybe aegerita
Appl. Microbiol. Biotechnol.
84
885-897
2009
Cyclocybe aegerita (B9W4V6)
brenda
Kinne, M.; Zeisig, C.; Ullrich, R.; Kayser, G.; Hammel, K.E.; Hofrichter, M.
Stepwise oxygenations of toluene and 4-nitrotoluene by a fungal peroxygenase
Biochem. Biophys. Res. Commun.
397
18-21
2010
Cyclocybe aegerita
brenda
Aranda, E.; Ullrich, R.; Hofrichter, M.
Conversion of polycyclic aromatic hydrocarbons, methyl naphthalenes and dibenzofuran by two fungal peroxygenases
Biodegradation
21
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2010
Cyclocybe aegerita, Coprinellus radians
brenda
Ullrich, R.; Liers, C.; Schimpke, S.; Hofrichter, M.
Purification of homogeneous forms of fungal peroxygenase
Biotechnol. J.
4
1619-1626
2009
Cyclocybe aegerita
brenda
Peng, L.; Wollenberger, U.; Hofrichter, M.; Ullrich, R.; Scheibner, K.; Scheller, F.W.
Bioelectrocatalytic properties of Agrocybe aegerita peroxygenase
Electrochim. Acta
55
7809-7813
2010
Cyclocybe aegerita
-
brenda
Ullrich, R.; Hofrichter, M.
The haloperoxidase of the agaric fungus Agrocybe aegerita hydroxylates toluene and naphthalene
FEBS Lett.
579
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2005
Cyclocybe aegerita
brenda
Ullrich, R.; Dolge, C.; Kluge, M.; Hofrichter, M.
Pyridine as novel substrate for regioselective oxygenation with aromatic peroxygenase from Agrocybe aegerita
FEBS Lett.
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2008
Cyclocybe aegerita
brenda
Kinne, M.; Poraj-Kobielska, M.; Ralph, S.A.; Ullrich, R.; Hofrichter, M.; Hammel, K.E.
Oxidative cleavage of diverse ethers by an extracellular fungal peroxygenase
J. Biol. Chem.
284
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2009
Cyclocybe aegerita
brenda
Kinne, M.; Ullrich, R.; Hammel, K.E.; Scheibner, K.; Hofrichter, M.
Regioselective preparation of (R)-2-(4-hydroxyphenoxy)propionic acid with a fungal peroxygenase
Tetrahedron Lett.
49
5950-5953
2008
Cyclocybe aegerita
-
brenda
Groebe, G.; Ullrich, R.; Pecyna, M.J.; Kapturska, D.; Friedrich, S.; Hofrichter, M.; Scheibner, K.
High-yield production of aromatic peroxygenase by the agaric fungus Marasmius rotula
AMB Express
1
31
2011
Marasmius rotula
brenda
Karich, A.; Kluge, M.; Ullrich, R.; Hofrichter, M.
Benzene oxygenation and oxidation by the peroxygenase of Agrocybe aegerita
AMB Express
3
5
2013
Cyclocybe aegerita (B9W4V6)
brenda
Yarman, A.; Groebe, G.; Neumann, B.; Kinne, M.; Gajovic-Eichelmann, N.; Wollenberger, U.; Hofrichter, M.; Ullrich, R.; Scheibner, K.; Scheller, F.W.
The aromatic peroxygenase from Marasmius rutola - a new enzyme for biosensor applications
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2012
Marasmius rotula
brenda
Babot, E.D.; del Rio, J.C.; Kalum, L.; Martinez, A.T.; Gutierrez, A.
Oxyfunctionalization of aliphatic compounds by a recombinant peroxygenase from Coprinopsis cinerea
Biotechnol. Bioeng.
110
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2013
Coprinopsis cinerea
brenda
Peter, S.; Kinne, M.; Ullrich, R.; Kayser, G.; Hofrichter, M.
Epoxidation of linear, branched and cyclic alkenes catalyzed by unspecific peroxygenase
Enzyme Microb. Technol.
52
370-376
2013
Cyclocybe aegerita
brenda
Hayakawa, S.; Matsumura, H.; Nakamura, N.; Yohda, M.; Ohno, H.
Identification of the rate-limiting step of the peroxygenase reactions catalyzed by the thermophilic cytochrome P450 from Sulfolobus tokodaii strain 7
FEBS J.
281
1409-1416
2014
Sulfurisphaera tokodaii, Sulfurisphaera tokodaii 7
brenda
Kluge, M.; Ullrich, R.; Scheibner, K.; Hofrichter, M.
Stereoselective benzylic hydroxylation of alkylbenzenes and epoxidation of styrene derivatives catalyzed by the peroxygenase of Agrocybe aegerita
Green Chem.
14
440-446
2012
Cyclocybe aegerita
-
brenda
Kluge, M.; Ullrich, R.; Scheibner, K.; Hofrichter, M.
Formation of naphthalene hydrates in the enzymatic conversion of 1,2-dihydronaphthalene by two fungal peroxygenases and subsequent naphthalene formation
J. Mol. Catal. B
103
56-60
2013
Cyclocybe aegerita, Coprinellus radians
-
brenda
Molina-Espeja, P.; Garcia-Ruiz, E.; Gonzalez-Perez, D.; Ullrich, R.; Hofrichter, M.; Alcalde, M.
Directed evolution of unspecific peroxygenase from Agrocybe aegerita
Appl. Environ. Microbiol.
80
3496-3507
2014
Cyclocybe aegerita (B9W4V6)
brenda
Poraj-Kobielska, M.; Peter, S.; Leonhardt, S.; Ullrich, R.; Scheibner, K.; Hofrichter, M.
Immobilization of unspecific peroxygenases (EC 1.11.2.1) in PVA/PEG gel and hollow fiber modules
Biochem. Eng. J.
98
144-150
2015
Cyclocybe aegerita
-
brenda
Kiebist, J.; Holla, W.; Heidrich, J.; Poraj-Kobielska, M.; Sandvoss, M.; Simonis, R.; Groebe, G.; Atzrodt, J.; Hofrichter, M.; Scheibner, K.
One-pot synthesis of human metabolites of SAR548304 by fungal peroxygenases
Bioorg. Med. Chem.
23
4324-4332
2015
Marasmius rotula
brenda
Lucas, F.; Babot, E.; Canellas, M.; Del Rio, J.; Kalum, L.; Ullrich, R.; Hofrichter, M.; Guallar, V.; Martinez, A.; Gutierrez, A.
Molecular determinants for selective C25-hydroxylation of vitamins D2 and D3 by fungal peroxygenases
Catal. Sci. Technol.
6
288-295
2015
Coprinopsis cinerea, Cyclocybe aegerita
-
brenda
Molina-Espeja, P.; Canellas, M.; Plou, F.J.; Hofrichter, M.; Lucas, F.; Guallar, V.; Alcalde, M.
Synthesis of 1-naphthol by a natural peroxygenase engineered by directed evolution
ChemBioChem
17
341-349
2016
Cyclocybe aegerita (B9W4V6)
brenda
Kiebist, J.; Schmidtke, K.U.; Zimmermann, J.; Kellner, H.; Jehmlich, N.; Ullrich, R.; Zaender, D.; Hofrichter, M.; Scheibner, K.
A peroxygenase from Chaetomium globosum catalyzes the selective oxygenation of testosterone
ChemBioChem
18
563-569
2017
Chaetomium globosum (Q2HHI5), Chaetomium globosum, Chaetomium globosum ATCC 6205 (Q2HHI5)
brenda
Hofrichter, M.; Ullrich, R.
Oxidations catalyzed by fungal peroxygenases
Curr. Opin. Chem. Biol.
19
116-125
2014
Coprinellus radians, Marasmius rotula, Cyclocybe aegerita (B9W4V6)
brenda
Molina-Espeja, P.; Ma, S.; Mate, D.M.; Ludwig, R.; Alcalde, M.
Tandem-yeast expression system for engineering and producing unspecific peroxygenase
Enzyme Microb. Technol.
73-74
29-33
2015
Cyclocybe aegerita
brenda
Carro, J.; Ferreira, P.; Rodriguez, L.; Prieto, A.; Serrano, A.; Balcells, B.; Arda, A.; Jimenez-Barbero, J.; Gutierrez, A.; Ullrich, R.; Hofrichter, M.; Martinez, A.T.
5-hydroxymethylfurfural conversion by fungal aryl-alcohol oxidase and unspecific peroxygenase
FEBS J.
282
3218-3229
2015
Cyclocybe aegerita, Cyclocybe aegerita DSM 22459
brenda
Peter, S.; Karich, A.; Ullrich, R.; Groebe, G.; Scheibner, K.; Hofrichter, M.
Enzymatic one-pot conversion of cyclohexane into cyclohexanone Comparison of four fungal peroxygenases
J. Mol. Catal. B
103
47-51
2014
Coprinopsis cinerea, Marasmius rotula, Cyclocybe aegerita (B9W4V6)
-
brenda
Karich, A.; Scheibner, K.; Ullrich, R.; Hofrichter, M.
Exploring the catalase activity of unspecific peroxygenases and the mechanism of peroxide-dependent heme destruction
J. Mol. Catal. B
134
238-246
2016
Coprinopsis cinerea, Marasmius rotula, Cyclocybe aegerita (B9W4V6)
-
brenda
Wang, X.; Ullrich, R.; Hofrichter, M.; Groves, J.T.
Heme-thiolate ferryl of aromatic peroxygenase is basic and reactive
Proc. Natl. Acad. Sci. USA
112
3686-3691
2015
Cyclocybe aegerita (B9W4V6)
brenda
Mate, D.M.; Palomino, M.A.; Molina-Espeja, P.; Martin-Diaz, J.; Alcalde, M.
Modification of the peroxygenative peroxidative activity ratio in the unspecific peroxygenase from Agrocybe aegerita by structure-guided evolution
Protein Eng. Des. Sel.
30
191-198
2017
Cyclocybe aegerita (B9W4V6)
brenda
Hayakawa, S.; Matsumura, H.; Nakamura, N.; Yohda, M.; Ohno, H.
Identification of the rate-limiting step of the peroxygenase reactions catalyzed by the thermophilic cytochrome P450 from Sulfolobus tokodaii strain 7
FEBS J.
281
1409-1416
2014
Sulfurisphaera tokodaii (Q972I2), Sulfurisphaera tokodaii 7 (Q972I2)
brenda
Rotilio, L.; Swoboda, A.; Ebner, K.; Rinnofner, C.; Glieder, A.; Kroutil, W.; Mattevi, A.
Structural and biochemical studies enlighten the unspecific peroxygenase from Hypoxylon sp. EC38 as an efficient oxidative biocatalyst
ACS Catal.
11
11511-11525
2021
Hypoxylon sp. EC38 (A0A1Y2TH07)
brenda
Knorrscheidt, A.; Soler, J.; Huenecke, N.; Puellmann, P.; Garcia-Borras, M.; Weissenborn, M.J.
Accessing chemo- and regioselective benzylic and aromatic oxidations by protein engineering of an unspecific peroxygenase
ACS Catal.
11
7327-7338
2021
Thermothelomyces thermophilus
brenda
Gonzalez-Benjumea, A.; Linde, D.; Carro, J.; Ullrich, R.; Hofrichter, M.; Martinez, A.; Gutierrez, A.
Regioselective and stereoselective epoxidation of n-3 and n-6 fatty acids by fungal peroxygenases
Antioxidants (Basel)
10
1888
2021
Achaetomiella virescens, Cyclocybe aegerita, Cyclocybe aegerita TM-A1
brenda
Linde, D.; Olmedo, A.; Gonzalez-Benjumea, A.; Estevez, M.; Renau-Minguez, C.; Carro, J.; Fernandez-Fueyo, E.; Gutierrez, A.; Martinez, A.
Two new unspecific peroxygenases from heterologous expression of fungal genes in Escherichia coli
Appl. Environ. Microbiol.
86
e02899-19
2020
Achaetomiella virescens, Daldinia caldariorum
brenda
de Santos, P.; Hoang, M.; Kiebist, J.; Kellner, H.; Ullrich, R.; Scheibner, K.; Hofrichter, M.; Liers, C.; Alcalde, M.
Functional expression of two unusual acidic peroxygenases from Candolleomyces aberdarensis in yeasts by adopting evolved secretion mutations
Appl. Environ. Microbiol.
87
1-14
2021
Candolleomyces aberdarensis
brenda
Martin-Diaz, J.; Molina-Espeja, P.; Hofrichter, M.; Hollmann, F.; Alcalde, M.
Directed evolution of unspecific peroxygenase in organic solvents
Biotechnol. Bioeng.
118
3002-3014
2021
Cyclocybe aegerita (B9W4V6)
brenda
Bormann, S.; Hertweck, D.; Schneider, S.; Bloh, J.Z.; Ulber, R.; Spiess, A.C.; Holtmann, D.
Modeling and simulation-based design of electroenzymatic batch processes catalyzed by unspecific peroxygenase from A. aegerita
Biotechnol. Bioeng.
118
7-16
2021
Cyclocybe aegerita
brenda
Faiza, M.; Huang, S.; Lan, D.; Wang, Y.
New insights on unspecific peroxygenases Superfamily reclassification and evolution
BMC Evol. Biol.
19
76
2019
Cyclocybe aegerita, Coprinellus radians, Marasmius rotula
brenda
Knorrscheidt, A.; Soler, J.; Huenecke, N.; Puellmann, P.; Garcia-Borras, M.; Weissenborn, M.
Simultaneous screening of multiple substrates with an unspecific peroxygenase enabled modified alkane and alkene oxyfunctionalisations
Catal. Sci. Technol.
11
6058-6064
2021
Thermothelomyces thermophilus
-
brenda
Aranda, C.; Ullrich, R.; Kiebist, J.; Scheibner, K.; Del Rio, J.; Hofrichter, M.; Martinez, A.; Gutierrez, A.
Selective synthesis of the resveratrol analogue 4,4'-dihydroxy-trans-stilbene and stilbenoids modification by fungal peroxygenases
Catal. Sci. Technol.
8
2394-2401
2018
Chaetomium globosum, Coprinopsis cinerea, Marasmius rotula (A0A023H437), Cyclocybe aegerita (B9W4V6)
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brenda
Aranda, C.; Municoy, M.; Guallar, V.; Kiebist, J.; Scheibner, K.; Ullrich, R.; Del Rio, J.; Hofrichter, M.; Martinez, A.; Gutierrez, A.
Selective synthesis of 4-hydroxyisophorone and 4-ketoisophorone by fungal peroxygenases
Catal. Sci. Technol.
9
1398-1405
2019
Chaetomium globosum, Coprinopsis cinerea, Humicola insolens, Marasmius rotula (A0A023H437), Cyclocybe aegerita (B9W4V6), Cyclocybe aegerita TM-A1 (B9W4V6), Chaetomium globosum DSM 62110, Marasmius rotula DSM 25031 (A0A023H437)
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brenda
Ullrich, R.; Poraj-Kobielska, M.; Herold-Majumdar, O.; Vind, J.; Hofrichter, M.
Synthesis of indigo-dyes from indole derivatives by unspecific peroxygenases and their application for in-situ dyeing
Catalysts
11
1495
2021
Coprinopsis cinerea, Humicola insolens, Cyclocybe aegerita
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brenda
Aranda, C.; Olmedo, A.; Kiebist, J.; Scheibner, K.; del Rio, J.; Martinez, A.; Gutierrez, A.
Selective epoxidation of fatty acids and fatty acid methyl esters by fungal peroxygenases
ChemCatChem
10
3964-3968
2018
Chaetomium globosum, Marasmius rotula
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brenda
Puellmann, P.; Knorrscheidt, A.; Muench, J.; Palme, P.; Hoehenwarter, W.; Marillonnet, S.; Alcalde, M.; Westermann, B.; Weissenborn, M.
A modular two yeast species secretion system for the production and preparative application of unspecific peroxygenases
Commun. Biol.
4
562
2021
Chaetomium globosum, Coprinopsis cinerea, Cyclocybe aegerita, Galerina marginata, Leptoxyphium fumago, Marasmius rotula, Thermothelomyces thermophilus
brenda
Kinner, A.; Rosenthal, K.; Luetz, S.
Identification and expression of new unspecific peroxygenases - Recent advances, challenges and opportunities
Front. Bioeng. Biotechnol.
9
705630
2021
Chaetomium globosum, Coprinellus radians, Candolleomyces aberdarensis, Coprinopsis verticillata, Marasmius wettsteinii, Marasmius rotula (A0A023H437), Cyclocybe aegerita (B9W4V6)
brenda
Lan, D.; Nie, X.; Ma, Y.; Wang, Y.
Recombinant expression and biochemical characterization of unspecific peroxygenase GmaUPOJ
Huanan Ligong Daxue Xuebao
49
22-28
2021
Galerina marginata
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brenda
Babot, E.; Aranda, C.; Del Rio, J.; Ullrich, R.; Kiebist, J.; Scheibner, K.; Hofrichter, M.; Martinez, A.; Gutierrez, A.
Selective oxygenation of ionones and damascones by fungal peroxygenases
J. Agric. Food Chem.
68
5375-5383
2020
Chaetomium globosum, Coprinopsis cinerea, Humicola insolens, Cyclocybe aegerita, Marasmius rotula, Daldinia caldariorum, Cyclocybe aegerita TM-A1, Chaetomium globosum DSM 62110, Marasmius rotula DSM 25031
brenda
Mireles, R.; Ramirez-Ramirez, J.; Alcalde, M.; Ayala, M.
Ether oxidation by an evolved fungal heme-peroxygenase Insights into substrate recognition and reactivity
J. Fungi (Basel)
7
608
2021
Cyclocybe aegerita (B9W4V6)
brenda
Ullrich, R.; Poraj-Kobielska, M.; Scholze, S.; Halbout, C.; Sandvoss, M.; Pecyna, M.J.; Scheibner, K.; Hofrichter, M.
Side chain removal from corticosteroids by unspecific peroxygenase
J. Inorg. Biochem.
183
84-93
2018
Marasmius wettsteinii, Marasmius rotula (A0A023H437), Marasmius rotula, Cyclocybe aegerita (B9W4V6), Marasmius wettsteinii DSM 106021
brenda
Jacob, S.; Bormann, S.; Becker, M.; Antelo, L.; Holtmann, D.; Thines, E.
Magnaporthe oryzae as an expression host for the production of the unspecific peroxygenase AaeUPO from the basidiomycete Agrocybe aegerita
MicrobiologyOpen
10
e1229
2021
Cyclocybe aegerita (B9W4V6)
brenda