1.11.2.3: plant seed peroxygenase
This is an abbreviated version!
For detailed information about plant seed peroxygenase, go to the full flat file.
Word Map on EC 1.11.2.3
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1.11.2.3
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arachidonic
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epoxyeicosatrienoic
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epoxide
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artery
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cyclooxygenase
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lipoxygenase
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vasodilation
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cyp2j2
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eicosanoids
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indomethacin
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hyperpolarizing
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miconazole
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endothelium-derived
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20-hete
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dihydroxyeicosatrienoic
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20-hydroxyeicosatetraenoic
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ms-ppoh
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cyp-derived
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edhfs
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arteriolar
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endothelium-dependent
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oleosins
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nordihydroguaiaretic
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vasodilatory
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dhets
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preglomerular
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5,6-epoxyeicosatrienoic
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large-conductance
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oxylipins
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17-octadecynoic
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eicosatetraynoic
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cyp-dependent
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sulfaphenazole
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hydroxyeicosatetraenoic
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p450-derived
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cross-recognition
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skf525a
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regioisomeric
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omega-hydroxylase
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p450-dependent
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14,15-epoxyeicosa-5z-enoic
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11,12-epoxyeicosatrienoic
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edhf-mediated
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epoxygenation
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5,8,11,14-eicosatetraynoic
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laser-doppler
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cyp2c11
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aacocf3
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iberiotoxin
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17-odya
- 1.11.2.3
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arachidonic
-
epoxyeicosatrienoic
- epoxide
- artery
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cyclooxygenase
- lipoxygenase
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vasodilation
- cyp2j2
-
eicosanoids
- indomethacin
-
hyperpolarizing
- miconazole
-
endothelium-derived
- 20-hete
-
dihydroxyeicosatrienoic
-
20-hydroxyeicosatetraenoic
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ms-ppoh
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cyp-derived
-
edhfs
-
arteriolar
-
endothelium-dependent
-
oleosins
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nordihydroguaiaretic
-
vasodilatory
-
dhets
-
preglomerular
-
5,6-epoxyeicosatrienoic
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large-conductance
- oxylipins
-
17-octadecynoic
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eicosatetraynoic
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cyp-dependent
- sulfaphenazole
-
hydroxyeicosatetraenoic
-
p450-derived
-
cross-recognition
- skf525a
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regioisomeric
-
omega-hydroxylase
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p450-dependent
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14,15-epoxyeicosa-5z-enoic
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11,12-epoxyeicosatrienoic
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edhf-mediated
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epoxygenation
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5,8,11,14-eicosatetraynoic
-
laser-doppler
- cyp2c11
- aacocf3
-
iberiotoxin
-
17-odya
Reaction
Synonyms
9-hydroperoxide fatty acid reductase, caleosin, caleosin-like protein, caleosin/peroxygenase, Clo-1, Clo-3, CLO/PXG, CLO3, CYP77B1, epoxygenase, fatty acid epoxygenase, hydrogen peroxide-reducible hemoprotein, hydroperoxide-dependent peroxygenase, peroxygenase RD20, peroxygenase, hydroperoxide-dependent hydroxylase, plant peroxygenase, PXG, PXG1, PXG2, PXG4, RD20, RD20/CLO3, soybean peroxygenase
ECTree
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Substrates Products
Substrates Products on EC 1.11.2.3 - plant seed peroxygenase
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REACTION DIAGRAM
(+)-(R)-limonene + H2O2
(R)-limonene trans-1,2-epoxide
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97% of products
-
?
(-)-(S)-limonene + H2O2
(S)-limonene cis-1,2-epoxide
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-
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
-
-
-
-
?
(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 + ?
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-
-
-
?
10-cis-heptadecenoic acid + cumene hydroperoxide
10,11-epoxyheptadecanoic acid + ?
94% of the activity with oleic acid
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-
?
10-cis-pentadecenoic acid + cumene hydroperoxide
10,11-epoxypentadecanoic acid + ?
98% of the activity with oleic acid
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-
?
13-hydroperoxy-9,11E,15Z-octadecatrienoic acid + H2O2
?
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-
-
?
13-hydroperoxyoctadecatrienoic acid + H2O2
13-hydroxyoctadecatrienoic acid + ?
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-
-
?
13-hydroxyoctadecatrienoic acid + H2O2
15,16-epoxy-13-hydroperoxyoctadecadienoic acid + ?
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-
-
?
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
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-
-
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?
2-hydroperoxyoctadecatrienoic acid + H2O2
2-hydroxyoctadecatrienoic acid + ?
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-
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?
2-methylhept-1-ene + tert-butyl hydroperoxide
2-methyl-2-pentyloxirane + ?
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-
-
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?
9-cis-hexadecenoic acid + cumene hydroperoxide
9,10-epoxy hexadecanoic acid + ?
89% of the activity with oleic acid
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-
?
aniline + cumene hydroperoxide
N-phenylhydroxylamine + H2O
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-
-
?
cis-2-heptene + tert-butyl hydroperoxide
2-butyl-3-methyl-cis-oxirane + ?
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-
93.9% yield
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?
cis-3-heptene + tert-butyl hydroperoxide
2-ethyl-3-propyl-cis-oxirane + ?
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-
72.7% yield
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?
cyclohexene + tert-butyl hydroperoxide
7-oxabicyclo-[4.1.0]-heptane + ?
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-
70.5% yield
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?
gamma-terpinene + H2O2
p-cymene
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in this reaction, hydroperoxide serves as hydrogen acceptor rather than an oxygen donor
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?
linoleate + tert-butyl hydroperoxide
(9Z)-12,13-epoxyoctadec-9-enoate + (12Z)-9,10-epoxyoctadec-12-enoate + 9,10-12,13-diepoxy-octadecanoate + ?
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23.4% yield, 25.4% yield and 46.7% yield, respectively
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?
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 + ?
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17.6% yield, 21.9% yield and 49.5% yield, respectively
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?
linoleic acid + 13-hydroperoxy-9,11-octadecadienoic acid
?
13-hydroperoxy-9,11-octadecadienoic acid is the most active cosubstrate
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-
?
linoleic acid + H2O2
15,16-epoxy-9,12-octadecadienoic acid + H2O
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25% yield
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?
linoleic acid + NADPH + H+
12,13-epoxy-octadec-cis-9-enoic acid + NADP+
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-
-
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?
linoleic acid + tert-butyl hydroperoxide
9,10-epoxy-octadecanoic acid + tert-butanol
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-
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?
linolenic acid + 13-hydroperoxy-9,11-octadecadienoic acid
?
13-hydroperoxy-9,11-octadecadienoic acid is the most active cosubstrate
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-
?
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
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?
methyl (13Z)-docos-13-enoate + tert-butyl hydroperoxide
methyl behenate 13,14-epoxide + H2O
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-
26.9% yield
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?
N-iso-butyl-(9Z,12Z,15Z)-octadecatrienamide + tert-butyl hydroperoxide
N-iso-butyl-9,10-15,16-diepoxy-(12Z)-octadecenamide + ?
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-
-
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?
oleate + tert-butyl hydroperoxide
methyl 9,10-epoxyoctadecanoate + ?
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-
99.8% yield
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?
oleate methyl ester + tert-butyl hydroperoxide
methyl 9,10-epoxyoctadecanoate + ?
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93.9% yield
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?
oleic acid + 13-hydroperoxy-9,11-octadecadienoic acid
?
13-hydroperoxy-9,11-octadecadienoic acid is the most active cosubstrate
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-
?
oleic acid + fatty acid hydroperoxide
cis-9,10-epoxystearic acid + ?
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-
-
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?
ricinoleate + tert-butyl hydroperoxide
9,10-epoxy-12-hydroxyoctadecanoate + ?
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73.6% yield
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?
trans-10,cis-12-linoleic acid + H2O2
12,13-epoxy-10-octadecenoic acid
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epoxidation occurs only at cis-double bond
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?
trans-2-heptene + tert-butyl hydroperoxide
2-butyl-3-methyl-trans-oxirane + ?
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26.6% yield
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?
(10E,12Z,9S)-9-hydroxyoctadec-10,12-dienoate + H2O
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-
-
-
?
(10E,12Z,9S)-9-hydroperoxy-octadec-10,12-dienoate + H2O2
(10E,12Z,9S)-9-hydroxyoctadec-10,12-dienoate + H2O
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-
-
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?
(10E,12Z,9S)-9-hydroperoxy-octadec-10,12-dienoate + H2O2
(10E,12Z,9S)-9-hydroxyoctadec-10,12-dienoate + H2O
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-
-
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?
(10E,12Z,9S)-9-hydroperoxy-octadec-10,12-dienoate + H2O2
(10E,12Z,9S)-9-hydroxyoctadec-10,12-dienoate + H2O
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-
-
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?
(10E,12Z,9S)-9-hydroperoxy-octadec-10,12-dienoate + H2O2
(10E,12Z,9S)-9-hydroxyoctadec-10,12-dienoate + H2O
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-
-
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?
(10E,12R,13S,9S)-12,13-epoxy-9-hydroxy-octadec-10-enoate + H2O
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-
-
-
?
(10E,12Z,9S)-9-hydroxy-octadec-10,12-dienoate + H2O2
(10E,12R,13S,9S)-12,13-epoxy-9-hydroxy-octadec-10-enoate + H2O
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-
-
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?
(10E,12Z,9S)-9-hydroxy-octadec-10,12-dienoate + H2O2
(10E,12R,13S,9S)-12,13-epoxy-9-hydroxy-octadec-10-enoate + H2O
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-
-
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?
(10E,12Z,9S)-9-hydroxy-octadec-10,12-dienoate + H2O2
(10E,12R,13S,9S)-12,13-epoxy-9-hydroxy-octadec-10-enoate + H2O
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-
-
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?
linoleate + H2O2
(12Z,9R,10S)-9,10-epoxyoctadec-12-enoate + H2O
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?
linoleic acid + cumene hydroperoxide
?
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64% conversion, physiological linoleic and linolenic acids are the preferred substrates for isoform PXG4
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?
linoleic acid + cumene hydroperoxide
?
47% of the activity with oleic acid
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?
cis-9,10-epoxystearic acid + ?
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?
additional information
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0.6% monoepoxy product and 91.6% diepoxy product
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?
methyl linolenate + tert-butyl hydroperoxide
additional information
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14.3% monoepoxy product and 78.3% diepoxy product
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?
additional information
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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
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?
additional information
?
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the enzyme does not oxidize diacylglycerol and triacylglycerol
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?
additional information
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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
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?
additional information
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the enzyme shows null reductase activity towards 9-hydroperoxy-10E,12Z-octadecadienoic and a weak activity towards 9-hydroperoxy-10E,12,15Z-octadecatrienoic acid
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additional information
?
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the enzyme shows null reductase activity towards 9-hydroperoxy-10E,12Z-octadecadienoic and a weak activity towards 9-hydroperoxy-10E,12,15Z-octadecatrienoic acid
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additional information
?
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peroxygenase exists in nature as a complex with a carotenoid-binding macromolecule
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?
additional information
?
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thiobenzamide and thioacetamide are no substrates
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?