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(+)-(R)-limonene + H2O2
(R)-limonene trans-1,2-epoxide
-
-
97% of products
-
?
(-)-(S)-limonene + H2O2
(S)-limonene cis-1,2-epoxide
-
-
88% of products
-
?
(10E,12Z,9S)-9-hydroperoxy-octadec-10,12-dienoate + H2O2
(10E,12Z,9S)-9-hydroxyoctadec-10,12-dienoate + H2O
(10E,12Z,9S)-9-hydroxy-octadec-10,12-dienoate + H2O2
(10E,12R,13S,9S)-12,13-epoxy-9-hydroxy-octadec-10-enoate + H2O
(10E,12Z,9S)-9-hydroxyoctadec-10,12-dienoate + H2O2
(10E,12R,13S,9S)-12,13-epoxy-9-hydroxy-octadec-10-enoate + H2O
-
-
-
-
?
(3Z)-hexenal + H2O2
(2E)-4-hydroxy-2-hexenal + H2O
-
-
-
-
?
(3Z)-nonenal + H2O2
(2E)-4-hydroxy-2-nonenal + H2O
-
-
-
-
?
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid + tert-butyl hydroperoxide
(12Z,15Z)-9,10-epoxyoctadeca-12,15-dienoic aicd + (9Z,12Z)-15,16-epoxy-9,12-octadecadienoic acid + ?
-
-
-
-
?
10-cis-heptadecenoic acid + cumene hydroperoxide
10,11-epoxyheptadecanoic acid + ?
94% of the activity with oleic acid
-
-
?
10-cis-pentadecenoic acid + cumene hydroperoxide
10,11-epoxypentadecanoic acid + ?
98% of the activity with oleic acid
-
-
?
2 linolenic acid + 3 tert-butyl hydroperoxide
(12Z,15Z)-9-epoxyoctadec-12,15-dienoic acid + (12Z)-9,15-diepoxyoctadec-12-enoic acid + 3 tert-butanol
-
-
-
-
?
2-methylhept-1-ene + tert-butyl hydroperoxide
2-methyl-2-pentyloxirane + ?
-
-
-
-
?
4-chloroaniline + H2O2
4-chloronitrosobenzene + ?
-
-
-
-
?
9-cis-hexadecenoic acid + cumene hydroperoxide
9,10-epoxy hexadecanoic acid + ?
89% of the activity with oleic acid
-
-
?
alpha-terpinene + H2O2
cis-1,4-dihydroxy-p-menth-2-ene
-
-
-
-
?
aniline + cumene hydroperoxide
?
aniline + cumene hydroperoxide
nitrosobenzene + ?
-
-
-
-
?
cis-2-heptene + tert-butyl hydroperoxide
2-butyl-3-methyl-cis-oxirane + ?
-
-
93.9% yield
-
?
cis-3-heptene + tert-butyl hydroperoxide
2-ethyl-3-propyl-cis-oxirane + ?
-
-
72.7% yield
-
?
cyclohexene + tert-butyl hydroperoxide
7-oxabicyclo-[4.1.0]-heptane + ?
-
-
70.5% yield
-
?
gamma-terpinene + H2O2
p-cymene
-
-
in this reaction, hydroperoxide serves as hydrogen acceptor rather than an oxygen donor
-
?
hept-1-ene + tert-butyl hydroperoxide
2-pentyloxirane + ?
-
-
2.8% yield
-
?
indole + H2O2
?
-
-
-
-
?
indole + H2O2
indoxyl + H2O
indole + linoleic acid hydroperoxide
?
-
-
-
-
?
linoleate + H2O2
(12Z,9R,10S)-9,10-epoxyoctadec-12-enoate + H2O
linoleate + tert-butyl hydroperoxide
(9Z)-12,13-epoxyoctadec-9-enoate + (12Z)-9,10-epoxyoctadec-12-enoate + 9,10-12,13-diepoxy-octadecanoate + ?
-
-
23.4% yield, 25.4% yield and 46.7% yield, respectively
-
?
linoleate methyl ester + tert-butyl hydroperoxide
methyl 12,13-epoxy-9(Z)-octadecenoate + methyl 9,10-epoxy-12(Z)-octadecenoate + methyl 9,10-12,13-diepoxyoctadecanoate + ?
-
-
17.6% yield, 21.9% yield and 49.5% yield, respectively
-
?
linoleic acid + cumene hydroperoxide
?
linoleic acid + H2O2
15,16-epoxy-9,12-octadecadienoic acid + H2O
-
-
25% yield
-
?
linoleic acid + H2O2
?
-
-
-
-
?
linoleic acid + tert-butyl hydroperoxide
9,10-epoxy-octadecanoic acid + tert-butanol
-
-
-
-
?
linolenic acid + cumene hydroperoxide
linolenic acid 9,10-15,16-diepoxide + ?
74% conversion, physiological linoleic and linolenic acids are the preferred substrates for isoform PXG4
major product, (R),(S)-epoxide enantiomers
-
?
methyl (13Z)-docos-13-enoate + tert-butyl hydroperoxide
methyl behenate 13,14-epoxide + H2O
-
-
26.9% yield
-
?
methyl 4-tolyl sulfide + cumene hydroperoxide
?
N-iso-butyl-(9Z,12Z,15Z)-octadecatrienamide + tert-butyl hydroperoxide
N-iso-butyl-9,10-15,16-diepoxy-(12Z)-octadecenamide + ?
-
-
-
-
?
nerol + H2O2
nerol-2,3-epoxide
-
-
sole product
-
?
oleate + tert-butyl hydroperoxide
methyl 9,10-epoxyoctadecanoate + ?
-
-
99.8% yield
-
?
oleate methyl ester + tert-butyl hydroperoxide
methyl 9,10-epoxyoctadecanoate + ?
-
-
93.9% yield
-
?
oleic acid + cumene hydroperoxide
?
oleic acid + cumene hydroperoxide
cis-9,10-epoxystearic acid + ?
oleic acid + fatty acid hydroperoxide
cis-9,10-epoxystearic acid + ?
-
-
-
-
?
oleic acid + H2O2
9,10-epoxyoctadecanoic acid
-
-
15% yield
-
?
oleic acid + H2O2
9,10-epoxystearic acid
-
-
-
-
?
parathion ethyl + cumene hydroperoxide
paraoxon + ?
phenylsulfide + H2O2
phenylsulfoxide + ?
-
-
-
-
?
pyrogallol + H2O2
purpurogallin + H2O
-
-
-
-
?
ricinoleate + tert-butyl hydroperoxide
9,10-epoxy-12-hydroxyoctadecanoate + ?
-
-
73.6% yield
-
?
styrene + tert-butyl hydroperoxide
epoxyethyl benzene + ?
-
-
57.4% yield
-
?
thioanisole + H2O2
?
-
-
-
-
?
thiobenzamide + cumene hydroperoxide
?
trans-10,cis-12-linoleic acid + H2O2
12,13-epoxy-10-octadecenoic acid
-
-
epoxidation occurs only at cis-double bond
-
-
trans-2-heptene + tert-butyl hydroperoxide
2-butyl-3-methyl-trans-oxirane + ?
-
-
26.6% yield
-
?
linolenate + tert-butyl hydroperoxide
additional information
-
(10E,12Z,9S)-9-hydroperoxy-octadec-10,12-dienoate + H2O2

(10E,12Z,9S)-9-hydroxyoctadec-10,12-dienoate + H2O
-
-
-
-
?
(10E,12Z,9S)-9-hydroperoxy-octadec-10,12-dienoate + H2O2
(10E,12Z,9S)-9-hydroxyoctadec-10,12-dienoate + H2O
-
-
-
-
?
(10E,12Z,9S)-9-hydroperoxy-octadec-10,12-dienoate + H2O2
(10E,12Z,9S)-9-hydroxyoctadec-10,12-dienoate + H2O
-
-
-
-
?
(10E,12Z,9S)-9-hydroperoxy-octadec-10,12-dienoate + H2O2
(10E,12Z,9S)-9-hydroxyoctadec-10,12-dienoate + H2O
-
-
-
-
?
(10E,12Z,9S)-9-hydroperoxy-octadec-10,12-dienoate + H2O2
(10E,12Z,9S)-9-hydroxyoctadec-10,12-dienoate + H2O
-
-
-
-
?
(10E,12Z,9S)-9-hydroxy-octadec-10,12-dienoate + H2O2

(10E,12R,13S,9S)-12,13-epoxy-9-hydroxy-octadec-10-enoate + H2O
-
-
-
-
?
(10E,12Z,9S)-9-hydroxy-octadec-10,12-dienoate + H2O2
(10E,12R,13S,9S)-12,13-epoxy-9-hydroxy-octadec-10-enoate + H2O
-
-
-
-
?
(10E,12Z,9S)-9-hydroxy-octadec-10,12-dienoate + H2O2
(10E,12R,13S,9S)-12,13-epoxy-9-hydroxy-octadec-10-enoate + H2O
-
-
-
-
?
(10E,12Z,9S)-9-hydroxy-octadec-10,12-dienoate + H2O2
(10E,12R,13S,9S)-12,13-epoxy-9-hydroxy-octadec-10-enoate + H2O
-
-
-
-
?
aniline + cumene hydroperoxide

?
-
-
-
-
?
aniline + cumene hydroperoxide
?
-
-
-
-
?
indole + H2O2

indoxyl + H2O
-
-
-
-
?
indole + H2O2
indoxyl + H2O
-
-
-
-
?
indole + H2O2
indoxyl + H2O
-
-
-
-
?
indole + H2O2
indoxyl + H2O
-
-
-
-
?
indole + H2O2
indoxyl + H2O
-
-
-
-
?
linoleate + H2O2

(12Z,9R,10S)-9,10-epoxyoctadec-12-enoate + H2O
-
-
-
-
?
linoleate + H2O2
(12Z,9R,10S)-9,10-epoxyoctadec-12-enoate + H2O
-
-
-
-
?
linoleate + H2O2
(12Z,9R,10S)-9,10-epoxyoctadec-12-enoate + H2O
-
-
-
-
?
linoleate + H2O2
(12Z,9R,10S)-9,10-epoxyoctadec-12-enoate + H2O
-
-
-
-
?
linoleate + H2O2
(12Z,9R,10S)-9,10-epoxyoctadec-12-enoate + H2O
-
-
-
-
?
linoleic acid + cumene hydroperoxide

?
-
-
-
-
?
linoleic acid + cumene hydroperoxide
?
-
64% conversion, physiological linoleic and linolenic acids are the preferred substrates for isoform PXG4
-
?
linoleic acid + cumene hydroperoxide
?
-
-
-
-
?
linoleic acid + cumene hydroperoxide
?
47% of the activity with oleic acid
-
-
?
methyl 4-tolyl sulfide + cumene hydroperoxide

?
-
-
-
-
?
methyl 4-tolyl sulfide + cumene hydroperoxide
?
-
-
-
-
?
oleate + H2O2

?
-
-
-
-
?
oleate + H2O2
?
-
-
-
-
?
oleate + H2O2
?
-
-
-
-
?
oleate + H2O2
?
-
-
-
-
?
oleate + H2O2
?
-
-
-
-
?
oleic acid + cumene hydroperoxide

?
-
-
-
-
?
oleic acid + cumene hydroperoxide
?
preferred substrate
-
-
?
oleic acid + cumene hydroperoxide
?
-
-
-
-
?
oleic acid + cumene hydroperoxide
?
-
-
-
-
?
oleic acid + cumene hydroperoxide

cis-9,10-epoxystearic acid + ?
-
-
-
-
?
oleic acid + cumene hydroperoxide
cis-9,10-epoxystearic acid + ?
-
-
-
-
?
parathion ethyl + cumene hydroperoxide

paraoxon + ?
-
-
-
-
?
parathion ethyl + cumene hydroperoxide
paraoxon + ?
-
-
-
-
?
parathion ethyl + cumene hydroperoxide
paraoxon + ?
-
-
-
-
?
thiobenzamide + cumene hydroperoxide

?
-
-
-
-
?
thiobenzamide + cumene hydroperoxide
?
-
-
-
-
?
linolenate + tert-butyl hydroperoxide

additional information
-
-
-
0.6% monoepoxy product and 91.6% diepoxy product
-
?
methyl linolenate + tert-butyl hydroperoxide
additional information
-
-
-
14.3% monoepoxy product and 78.3% diepoxy product
-
?
additional information
?
-
enzyme is an efficient fatty acid epoxygenase, catalyzing the oxidation of cis double bonds of unsaturated fatty acids. The C-12,13 double bond of these unsaturated fatty acids is the least favoured. Isoform PXG4 catalyzes exclusively the formation of (R),(S)-epoxide enantiomers, which is the absolute stereochemistry of the epoxides found in planta. Poor substrate: oleic acid methyl ester
-
-
-
additional information
?
-
-
the enzyme does not oxidize diacylglycerol and triacylglycerol
-
-
-
additional information
?
-
isoform PXG1 catalyzes the strictly hydroperoxide-dependent epoxidation of unsaturated fatty acids. It prefers hydroperoxy-trienoic acids over hydroperoxydienoic acids as oxygen donors to oxidize a wide range of unsaturated fatty acids with cis double bonds. Phospholipids and acyl-CoA are not effective substrates and it will only use free fatty acid or fatty acid methyl esters as substrates. Both hydroperoxy-dienoic and hydroperoxy-trienoic acids are effectively utilized as oxygen donors, with hydroperoxy-trienoic acids being more efficiently reduced
-
-
-
additional information
?
-
-
peroxygenase exists in nature as a complex with a carotenoid-binding macromolecule
-
-
-
additional information
?
-
-
thiobenzamide and thioacetamide are no substrates
-
-
-
additional information
?
-
-
no substrate: geraniol
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid + tert-butyl hydroperoxide
(12Z,15Z)-9,10-epoxyoctadeca-12,15-dienoic aicd + (9Z,12Z)-15,16-epoxy-9,12-octadecadienoic acid + ?
-
-
-
-
?
2 linolenic acid + 3 tert-butyl hydroperoxide
(12Z,15Z)-9-epoxyoctadec-12,15-dienoic acid + (12Z)-9,15-diepoxyoctadec-12-enoic acid + 3 tert-butanol
-
-
-
-
?
aniline + cumene hydroperoxide
?
aniline + cumene hydroperoxide
nitrosobenzene + ?
-
-
-
-
?
linoleic acid + cumene hydroperoxide
?
linoleic acid + tert-butyl hydroperoxide
9,10-epoxy-octadecanoic acid + tert-butanol
-
-
-
-
?
linolenic acid + cumene hydroperoxide
linolenic acid 9,10-15,16-diepoxide + ?
Q9CAB7
74% conversion, physiological linoleic and linolenic acids are the preferred substrates for isoform PXG4
major product, (R),(S)-epoxide enantiomers
-
?
methyl 4-tolyl sulfide + cumene hydroperoxide
?
oleic acid + cumene hydroperoxide
?
-
-
-
-
?
oleic acid + cumene hydroperoxide
cis-9,10-epoxystearic acid + ?
oleic acid + fatty acid hydroperoxide
cis-9,10-epoxystearic acid + ?
-
-
-
-
?
thiobenzamide + cumene hydroperoxide
?
additional information
?
-
aniline + cumene hydroperoxide

?
-
-
-
-
?
aniline + cumene hydroperoxide
?
-
-
-
-
?
linoleic acid + cumene hydroperoxide

?
-
-
-
-
?
linoleic acid + cumene hydroperoxide
?
Q9CAB7
-
64% conversion, physiological linoleic and linolenic acids are the preferred substrates for isoform PXG4
-
?
linoleic acid + cumene hydroperoxide
?
-
-
-
-
?
methyl 4-tolyl sulfide + cumene hydroperoxide

?
-
-
-
-
?
methyl 4-tolyl sulfide + cumene hydroperoxide
?
-
-
-
-
?
oleic acid + cumene hydroperoxide

cis-9,10-epoxystearic acid + ?
-
-
-
-
?
oleic acid + cumene hydroperoxide
cis-9,10-epoxystearic acid + ?
-
-
-
-
?
thiobenzamide + cumene hydroperoxide

?
-
-
-
-
?
thiobenzamide + cumene hydroperoxide
?
-
-
-
-
?
additional information

?
-
Q9CAB7
enzyme is an efficient fatty acid epoxygenase, catalyzing the oxidation of cis double bonds of unsaturated fatty acids. The C-12,13 double bond of these unsaturated fatty acids is the least favoured. Isoform PXG4 catalyzes exclusively the formation of (R),(S)-epoxide enantiomers, which is the absolute stereochemistry of the epoxides found in planta. Poor substrate: oleic acid methyl ester
-
-
-
additional information
?
-
-
the enzyme does not oxidize diacylglycerol and triacylglycerol
-
-
-
additional information
?
-
-
peroxygenase exists in nature as a complex with a carotenoid-binding macromolecule
-
-
-
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Henriksen, A.; Mirza, O.; Indiani, C.; Teilum, K.; Smulevich, G.; Welinder, K.G.; Gajhede, M.
Structure of soybean seed coat peroxidase: a plant peroxidase with unusual stability and haem-apoprotein interactions
Protein Sci.
10
108-115
2001
Soja hispida
brenda
Magri, M.; Miranda, M.; Cascone, O.
Immobilization of soybean seed coat peroxidase on polyaniline: Synthesis optimization and catalytic properties
Biocatal. Biotransform.
23
339-346
2005
Glycine max
-
brenda
Doerge, D.R.; Corbett, M.D.
Oxidation of organosulfur compounds by the microsomal fraction of germinating pea seeds (Pisum sativum)
Biochem. Biophys. Res. Commun.
121
1001-1005
1984
Pisum sativum
brenda
Takamura, H.; Gardner, H.W.
Oxygenation of (3Z)-alkenal to (2E)-4-hydroxy-2-alkenal in soybean seed (Glycine max L.)
Biochim. Biophys. Acta
1303
83-91
1996
Glycine max
brenda
Piazza, G.J.; Foglia, T.A.
Synthesis of a fatty tetrahydroxyamide using peroxygenase from oat seeds
J. Am. Oil Chem. Soc.
81
933-937
2004
Avena sativa
brenda
Piazza, G.J.; Foglia, T.A.
One-pot synthesis of fatty acid epoxides from triacylglycerols using enzymes present in oat seeds
J. Am. Oil Chem. Soc.
83
1021-1025
2006
Avena sativa
brenda
Ishimaru, A.
Purification and characterization of solubilized peroxygenase from microsomes of pea seeds
J. Biol. Chem.
254
8427-8433
1979
Pisum sativum
brenda
Kandel, S.; Morant, M.; Benveniste, I.; Blee, E.; Werck-Reichhart, D.; Pinot, F.
Cloning, functional expression, and characterization of CYP709C1, the first sub-terminal hydroxylase of long chain fatty acid in plants. Induction by chemicals and methyl jasmonate
J. Biol. Chem.
280
35881-35889
2005
Triticum aestivum
brenda
Hanano, A.; Burcklen, M.; Flenet, M.; Ivancich, A.; Louwagie, M.; Garin, J.; Blee, E.
Plant seed peroxygenase is an original heme-oxygenase with an EF-hand calcium binding motif
J. Biol. Chem.
281
33140-33151
2006
Arabidopsis thaliana, Avena sativa
brenda
Piazza, G.J.; Nunez, A.; Foglia, T.A.
Epoxidation of fatty acids, fatty methyl esters, and alkenes by immobilized oat seed peroxygenase
J. Mol. Catal. B
21
143-151
2003
Avena sativa
-
brenda
Lequeu, J.; Fauconnier, M.L.; Chammai, A.; Bronner, R.; Blee, E.
Formation of plant cuticle: evidence for the occurrence of the peroxygenase pathway
Plant J.
36
155-164
2003
Avena sativa, Glycine max, Zea mays
brenda
Partridge, M.; Murphy, D.J.
Roles of a membrane-bound caleosin and putative peroxygenase in biotic and abiotic stress responses in Arabidopsis
Plant Physiol. Biochem.
47
796-806
2009
Arabidopsis thaliana
brenda
Hamberg, M.; Hamberg, G.
Peroxygenase-catalyzed fatty acid epoxidation in cereal seeds. Sequential oxidation of linoleic acid into 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acid
Plant Physiol.
110
807-815
1996
Avena sativa, Hordeum vulgare, Hordeum vulgare subsp. vulgare, Secale cereale, Triticum aestivum
brenda
Blee, E.; Flenet, M.; Boachon, B.; Fauconnier, M.L.
A non-canonical caleosin from Arabidopsis efficiently epoxidizes physiological unsaturated fatty acids with complete stereoselectivity
FEBS J.
279
3981-3995
2012
Arabidopsis thaliana (Q9CAB7)
brenda
Fuchs, C.; Schwab, W.
Epoxidation, hydroxylation and aromatization is catalyzed by a peroxygenase from Solanum lycopersicum
J. Mol. Catal. B
96
52-60
2013
Solanum lycopersicum
-
brenda
Kim, Y.Y.; Jung, K.W.; Yoo, K.S.; Jeung, J.U.; Shin, J.S.
A stress-responsive caleosin-like protein, AtCLO4, acts as a negative regulator of ABA responses in Arabidopsis
Plant Cell Physiol.
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874-884
2011
Arabidopsis thaliana (Q9CAB7)
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Meesapyodsuk, D.; Qiu, X.
A peroxygenase pathway involved in the biosynthesis of epoxy fatty acids in oat
Plant Physiol.
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2011
Avena sativa (G1JSL4)
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