Information on EC 1.11.2.3 - plant seed peroxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.11.2.3
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RECOMMENDED NAME
GeneOntology No.
plant seed peroxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
R1H + R2OOH = R1OH + R2OH
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
epoxidation
sulfoxidation
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
cutin biosynthesis
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vernolate biosynthesis III
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Cutin, suberine and wax biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
substrate:hydroperoxide oxidoreductase (RH-hydroxylating or epoxidising)
A heme protein with calcium binding motif (caleosin-type). Enzymes of this type include membrane-bound proteins found in seeds of different plants. They catalyse the direct transfer of one oxygen atom from an organic hydroperoxide, which is reduced into its corresponding alcohol to a substrate which will be oxidized. Reactions catalysed include hydroxylation, epoxidation and sulfoxidation. Preferred substrate and co-substrate are unsaturated fatty acids and fatty acid hydroperoxides, respectively. Plant seed peroxygenase is involved in the synthesis of cutin.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Soja hispida
soybean
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-(R)-limonene + H2O2
(R)-limonene trans-1,2-epoxide
show the reaction diagram
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97% of products
-
?
(-)-(S)-limonene + H2O2
(S)-limonene cis-1,2-epoxide
show the reaction diagram
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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
show the reaction diagram
(10E,12Z,9S)-9-hydroxy-octadec-10,12-dienoate + H2O2
(10E,12R,13S,9S)-12,13-epoxy-9-hydroxy-octadec-10-enoate + H2O
show the reaction diagram
(10E,12Z,9S)-9-hydroxyoctadec-10,12-dienoate + H2O2
(10E,12R,13S,9S)-12,13-epoxy-9-hydroxy-octadec-10-enoate + H2O
show the reaction diagram
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-
-
-
?
(3Z)-hexenal + H2O2
(2E)-4-hydroxy-2-hexenal + H2O
show the reaction diagram
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-
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?
(3Z)-nonenal + H2O2
(2E)-4-hydroxy-2-nonenal + H2O
show the reaction diagram
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?
(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 + ?
show the reaction diagram
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-
-
?
10-cis-heptadecenoic acid + cumene hydroperoxide
10,11-epoxyheptadecanoic acid + ?
show the reaction diagram
94% of the activity with oleic acid
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?
10-cis-pentadecenoic acid + cumene hydroperoxide
10,11-epoxypentadecanoic acid + ?
show the reaction diagram
98% of the activity with oleic 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
show the reaction diagram
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-
-
?
2-methylhept-1-ene + tert-butyl hydroperoxide
2-methyl-2-pentyloxirane + ?
show the reaction diagram
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-
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?
4-chloroaniline + H2O2
4-chloronitrosobenzene + ?
show the reaction diagram
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-
-
?
9-cis-hexadecenoic acid + cumene hydroperoxide
9,10-epoxy hexadecanoic acid + ?
show the reaction diagram
89% of the activity with oleic acid
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?
alpha-terpinene + H2O2
cis-1,4-dihydroxy-p-menth-2-ene
show the reaction diagram
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-
-
?
aniline + cumene hydroperoxide
?
show the reaction diagram
aniline + cumene hydroperoxide
nitrosobenzene + ?
show the reaction diagram
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-
-
-
?
cis-2-heptene + tert-butyl hydroperoxide
2-butyl-3-methyl-cis-oxirane + ?
show the reaction diagram
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93.9% yield
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?
cis-3-heptene + tert-butyl hydroperoxide
2-ethyl-3-propyl-cis-oxirane + ?
show the reaction diagram
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72.7% yield
-
?
cyclohexene + tert-butyl hydroperoxide
7-oxabicyclo-[4.1.0]-heptane + ?
show the reaction diagram
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70.5% yield
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?
gamma-terpinene + H2O2
p-cymene
show the reaction diagram
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in this reaction, hydroperoxide serves as hydrogen acceptor rather than an oxygen donor
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?
hept-1-ene + tert-butyl hydroperoxide
2-pentyloxirane + ?
show the reaction diagram
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2.8% yield
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?
indole + H2O2
?
show the reaction diagram
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?
indole + H2O2
indoxyl + H2O
show the reaction diagram
indole + linoleic acid hydroperoxide
?
show the reaction diagram
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?
linoleate + H2O2
(12Z,9R,10S)-9,10-epoxyoctadec-12-enoate + H2O
show the reaction diagram
linoleate + tert-butyl hydroperoxide
(9Z)-12,13-epoxyoctadec-9-enoate + (12Z)-9,10-epoxyoctadec-12-enoate + 9,10-12,13-diepoxy-octadecanoate + ?
show the reaction diagram
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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 + ?
show the reaction diagram
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17.6% yield, 21.9% yield and 49.5% yield, respectively
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?
linoleic acid + cumene hydroperoxide
?
show the reaction diagram
linoleic acid + H2O2
15,16-epoxy-9,12-octadecadienoic acid + H2O
show the reaction diagram
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25% yield
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?
linoleic acid + H2O2
?
show the reaction diagram
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-
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?
linoleic acid + tert-butyl hydroperoxide
9,10-epoxy-octadecanoic acid + tert-butanol
show the reaction diagram
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?
linolenic acid + cumene hydroperoxide
linolenic acid 9,10-15,16-diepoxide + ?
show the reaction diagram
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
show the reaction diagram
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26.9% yield
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?
methyl 4-tolyl sulfide + cumene hydroperoxide
?
show the reaction diagram
N-iso-butyl-(9Z,12Z,15Z)-octadecatrienamide + tert-butyl hydroperoxide
N-iso-butyl-9,10-15,16-diepoxy-(12Z)-octadecenamide + ?
show the reaction diagram
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?
nerol + H2O2
nerol-2,3-epoxide
show the reaction diagram
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sole product
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?
oleate + H2O2
?
show the reaction diagram
oleate + tert-butyl hydroperoxide
methyl 9,10-epoxyoctadecanoate + ?
show the reaction diagram
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99.8% yield
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?
oleate methyl ester + tert-butyl hydroperoxide
methyl 9,10-epoxyoctadecanoate + ?
show the reaction diagram
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93.9% yield
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?
oleic acid + cumene hydroperoxide
?
show the reaction diagram
oleic acid + cumene hydroperoxide
cis-9,10-epoxystearic acid + ?
show the reaction diagram
oleic acid + fatty acid hydroperoxide
cis-9,10-epoxystearic acid + ?
show the reaction diagram
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?
oleic acid + H2O2
9,10-epoxyoctadecanoic acid
show the reaction diagram
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15% yield
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?
oleic acid + H2O2
9,10-epoxystearic acid
show the reaction diagram
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?
parathion ethyl + cumene hydroperoxide
paraoxon + ?
show the reaction diagram
phenylsulfide + H2O2
phenylsulfoxide + ?
show the reaction diagram
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-
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?
pyrogallol + H2O2
purpurogallin + H2O
show the reaction diagram
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?
ricinoleate + tert-butyl hydroperoxide
9,10-epoxy-12-hydroxyoctadecanoate + ?
show the reaction diagram
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73.6% yield
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?
styrene + tert-butyl hydroperoxide
epoxyethyl benzene + ?
show the reaction diagram
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57.4% yield
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?
thioanisole + H2O2
?
show the reaction diagram
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?
thiobenzamide + cumene hydroperoxide
?
show the reaction diagram
trans-10,cis-12-linoleic acid + H2O2
12,13-epoxy-10-octadecenoic acid
show the reaction diagram
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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 + ?
show the reaction diagram
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26.6% yield
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?
linolenate + tert-butyl hydroperoxide
additional information
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(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 + ?
show the reaction diagram
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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
show the reaction diagram
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-
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?
aniline + cumene hydroperoxide
?
show the reaction diagram
aniline + cumene hydroperoxide
nitrosobenzene + ?
show the reaction diagram
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-
-
?
linoleic acid + cumene hydroperoxide
?
show the reaction diagram
linoleic acid + tert-butyl hydroperoxide
9,10-epoxy-octadecanoic acid + tert-butanol
show the reaction diagram
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-
-
-
?
linolenic acid + cumene hydroperoxide
linolenic acid 9,10-15,16-diepoxide + ?
show the reaction diagram
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
?
show the reaction diagram
oleic acid + cumene hydroperoxide
?
show the reaction diagram
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-
-
-
?
oleic acid + cumene hydroperoxide
cis-9,10-epoxystearic acid + ?
show the reaction diagram
oleic acid + fatty acid hydroperoxide
cis-9,10-epoxystearic acid + ?
show the reaction diagram
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-
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?
thiobenzamide + cumene hydroperoxide
?
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
no cofactors required
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe
Soja hispida
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additional information
-
peroxygenase activity is not stimulated by Ca2+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-mercaptoethanol
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the sulfoxidation of thiobenzamide, catalyzed by isoform PXG1, is completely abolished in the presence of 1 mM 2-mercaptoethanol (competitive inhibitor)
disulfoton
H2O2
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the enzyme is inhibited by hydrogen peroxide preincubation
O,O-dimethyl O-(4-nitrophenyl)phosphorothioate
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parathion
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suicide inhibition
parathion ethyl
parathion methyl
phorate
terbufos
additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.12
4-chloroaniline
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pH and temperature not specified in the publication
1.3
H2O2
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partially purified enzyme, at pH 7.2 and 25C
0.07 - 0.08
indole
0.078
linoleic acid
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pH 6.0, 40C
0.26
linoleic acid hydroperoxide
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partially purified enzyme, at pH 7.2 and 25C
0.071
oleic acid
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pH 6.0, 40C
0.031
phenylsulfide
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pH and temperature not specified in the publication
0.123
thioanisole
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pH and temperature not specified in the publication
0.815
trans-10,cis-12-linoleic acid
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pH 6.0, 40C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.01
terbufos
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.15
disulfoton
0.13
O,O-dimethyl O-(4-nitrophenyl)phosphorothioate
Avena sativa
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in 0.1 M KH2PO4, at pH 7.0 and 26C
0.08
parathion
0.13
parathion methyl
0.09
phorate
0.02
terbufos
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.54
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unpurified microsomal enzyme, at pH 7.2 and 25C
3.4
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partially purified microsomal enzyme, at pH 7.2 and 25C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 7
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7.1
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partially purified enzyme, using 0.2 mM linoleic acid hydroperoxide as cosubstrate
7.2
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membrane-bound enzyme, using 0.2 mM linoleic acid hydroperoxide as cosubstrate; partially purified enzyme, using 1.0 mM H2O2 as cosubstrate
8.7
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membrane-bound enzyme, using 1.0 mM H2O2 as cosubstrate
9.5
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for both (2E)-4-hydroxy-2-hexenal and (2E)-4-hydroxy-2-nonenal formation the optimal pH is 9.5
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
55
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immobilized enzyme
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
dominantly expressed in vascular bundles in most organs as well as in the guard cells
Manually annotated by BRENDA team
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isoform Clo-3
Manually annotated by BRENDA team
dominantly expressed in vascular bundles in most organs as well as in the guard cells
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
27000
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SDS-PAGE
32000
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SDS-PAGE
37000
Soja hispida
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230000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
heterotetramer
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3 * 62500 + 1 * 41000, SDS-PAGE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
phosphoprotein
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Clo-3 is phosphorylated in response to salt stress
sumoylation
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isoform PXG1 possesses a high sumoylation potentiality at the position Lys-196
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21, determined at -173C as TRIS-complex, 2.8 A resolution, 88.2% overall completeness
Soja hispida
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
enzyme immobilized on various polyaniline-based polymers retains 80% of its activity for 15 weeks. Immobilized enzyme shows a greatly improved tolerance to different organic solvents
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ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
acetonitrile
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soluble enzyme loses about 90% of its activity in 70% acetonitrile, the immobilized enzyme loses about 30% of its activity
Glycerol
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20% (v/v) glycerol remarkably stabilizes the enzyme. The enzyme extracted with cholate or deoxycholate is very stable in the presence of glycerol
Triton X-100
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the solubilized peroxygenase is unstable especially in the presence of Triton X-100
Tween
-
the solubilized peroxygenase is unstable especially in the presence of Tween 80
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DEAE-Trisacryl 300 gel filtration and CM-Sepharose column chromatography
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DEAF-cellulose column chromatography and agarose gel column chromatography
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Ni-NTA column chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21
Soja hispida
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expressed in Saccharomyces cerevisiae
expression in Escherichia coli
expression in Pichia pastoris and Escherichia coli
expression in Saccharomyces cerevisiae
expression in Saccharomyces cervisiae
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression is down-regulated following exposure to exogenous abscisic acid and salt stress
isoform Clo-3 is highly upregulated following exposure to abiotic stresses, such as salt and drought or treatment with salicylic acid or 2,6-dichloroisonicotinic acid, and to biotic stress such as Leptosphaeria maculans infection
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
H138V
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the mutant possess only 4% of the heme content wild type isoform PXG1
H70V
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the heme content of the mutant is barely measurable (less than 1%) as compared to the wild type isoform PXG1