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Information on EC 1.3.1.42 - 12-oxophytodienoate reductase and Organism(s) Arabidopsis thaliana and UniProt Accession Q9FUP0

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IUBMB Comments
Involved in the conversion of linolenate into jasmonate in Zea mays.
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This record set is specific for:
Arabidopsis thaliana
UNIPROT: Q9FUP0
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Word Map
The taxonomic range for the selected organisms is: Arabidopsis thaliana
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
12-oxophytodienoate reductase, 12-oxo-phytodienoic acid reductase, csopr3, osopr7, opda reductase, taopr1, 12-oxophytodienoate reductase 3, osopr8, oprii, 12-oxophytodienoate-10,11-reductase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
12-oxo-phytodienoate acid reductase
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12-oxophytodienoate reductase 3
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oxophytodienoate reductase
-
phytodienoic acid reductase
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12-oxo-phytodienoic acid reductase
-
-
-
-
12-oxophytodienoate reductase isoform 3
-
-
oxophytodienoate reductase
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phytodienoic acid reductase
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
-
-
-
-
oxidation
-
-
-
-
reduction
SYSTEMATIC NAME
IUBMB Comments
8-[(1R,2R)-3-oxo-2-{(Z)-pent-2-enyl}cyclopentyl]octanoate:NADP+ 4-oxidoreductase
Involved in the conversion of linolenate into jasmonate in Zea mays.
CAS REGISTRY NUMBER
COMMENTARY hide
101150-03-2
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(15Z)-12-oxophyto-10,15-dienoate + NADPH + H+
8-[(1R,2R)-3-oxo-2-((Z)-pent-2-enyl)cyclopentyl]octanoate + NADP+
show the reaction diagram
-
-
-
?
(9S,13S)-12-oxophytodienoic acid + NADPH + H+
3-oxo-2-((2Z)-pentenyl)-cyclopentane-1-octanoic acid + NADP+
show the reaction diagram
OPR3 is involved in jasmonic acid biosynthesis
-
-
?
1,4-benzoquinone + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
2-methylcyclopent-2-en-1-one + NADPH + H+
(2S)-2-methylcyclopentanone + NAD+
show the reaction diagram
-
-
-
?
maleic acid + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
methyl vinyl ketone + NADPH + H+
hexanal + NADP+
show the reaction diagram
-
-
-
?
N-ethyl-maleimide + NADPH + H+
? + NAD+
show the reaction diagram
-
-
-
?
trans-hex-2-enal + NADPH + H+
hexanal + NADP+
show the reaction diagram
-
-
-
?
(15Z)-12-oxophyto-10,15-dienoate + NADPH
8-[(1R,2R)-3-oxo-2-((Z)-pent-2-enyl)cyclopentyl]octanoate + NADP+
show the reaction diagram
(9S,13S)-(15Z)-12-oxophyto-10,15-dienoate + NADPH
(9S,13S)-8-[(1R,2R)-3-oxo-2-((Z)-pent-2-enyl)cyclopentyl]octanoate + NADP+
show the reaction diagram
(9S,13S)-12-oxo-phytodienoic acid + NADPH
3-oxo-2((2Z)-pentenyl)-cyclopentane-1-octanoic acid + NADP+
show the reaction diagram
12-oxo-cis-phythodienoic acid + NADPH
cis-3-oxo-2-(2'-pentenyl)cyclopentane-1-octanoic acid + NADP+
show the reaction diagram
9S,13R-12-oxo-phytodienoic acid + NADPH
? + NADP+
show the reaction diagram
-
does not utilize 13S-configured isomers
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(9S,13S)-12-oxophytodienoic acid + NADPH + H+
3-oxo-2-((2Z)-pentenyl)-cyclopentane-1-octanoic acid + NADP+
show the reaction diagram
OPR3 is involved in jasmonic acid biosynthesis
-
-
?
(15Z)-12-oxophyto-10,15-dienoate + NADPH
8-[(1R,2R)-3-oxo-2-((Z)-pent-2-enyl)cyclopentyl]octanoate + NADP+
show the reaction diagram
-
-
-
-
?
(9S,13S)-(15Z)-12-oxophyto-10,15-dienoate + NADPH
(9S,13S)-8-[(1R,2R)-3-oxo-2-((Z)-pent-2-enyl)cyclopentyl]octanoate + NADP+
show the reaction diagram
-
product is an intermediate in the jasmonate biosynthesis
-
-
?
(9S,13S)-12-oxo-phytodienoic acid + NADPH
3-oxo-2((2Z)-pentenyl)-cyclopentane-1-octanoic acid + NADP+
show the reaction diagram
12-oxo-cis-phythodienoic acid + NADPH
cis-3-oxo-2-(2'-pentenyl)cyclopentane-1-octanoic acid + NADP+
show the reaction diagram
9S,13R-12-oxo-phytodienoic acid + NADPH
? + NADP+
show the reaction diagram
-
does not utilize 13S-configured isomers
-
-
?
additional information
?
-
-
phylogenetic analysis, isozyme OPR3 is induced in self-defense signalling, enzyme is involved in octadecanoid and jasmonate biosynthesis with differential roles for in the local versus the systemic wound response, cDNA micro array analysis
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-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
FMN
absorption maxima at 280, 374 and 467 nm
flavin
-
dependent on
FMN
-
one molecule per enzyme monomer
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2,4,6-trinitrotoluene
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0283
(15Z)-12-oxophyto-10,15-dienoate
pH 7.2, temperature not specified in the publication
1.967
2-methylcyclopent-2-en-1-one
pH 7.2, temperature not specified in the publication
0.0385
Methyl vinyl ketone
pH 7.2, temperature not specified in the publication
4.36
trans-hex-2-enal
pH 7.2, temperature not specified in the publication
0.035
(9S,13S)-12-oxophytodienoic acid
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
13.5
substrate methyl vinyl ketone, pH 7.2, temperature not specified in the publication
2
substrate (15Z)-12-oxophyto-10,15-dienoate, pH 7.2, temperature not specified in the publication
2.5
substrate 2-methylcyclopent-2-en-1-one, pH 7.2, temperature not specified in the publication
22.8
substrate N-ethyl-maleimide, pH 7.2, temperature not specified in the publication
26.9
substrate 1,4-benzoquinone, pH 7.2, temperature not specified in the publication
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
OPR overexpressing line
Manually annotated by BRENDA team
OPR overexpressing line
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
isozymes OPR1 and OPR2
Manually annotated by BRENDA team
-
isozyme OPR3
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
in plants, OPRs belong to the old yellow enzyme family and form multigene families, phylogenetic analysis, structural evolution and functional divergence among OPR paralogues in plants, 6 major green plant lineages, overview
metabolism
one of the key genes of the jasmonic acid biosynthesis pathway
physiological function
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
OPR3_ARATH
391
0
42691
Swiss-Prot
Chloroplast (Reliability: 5)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
41170
predicted from amino acid sequence
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 42000, SDS-PAGE, x * 42690, calculated from sequence
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
10 mg/ml purified recombinant isozyme OPR3 in 100 mM MES, pH 6.0, 100 mM NaCl, 0.3 mM TCEP, hanging drop vapour diffusion method, 0.002 ml protein solution with equal volume of well solution containing 8.75-10.0% monomethyl ether polyethylene glycol 5000, 0.1 M triethanolamine, pH 8.0, 0.275-0.35 M glycine, crystals are harvested into a cryoprotectant solution containing 12% monomethyl ether polyethylene glycol 5000, 0.1 M triethanolamine, pH 8.0, 0.4 M glycine, and 25% PEG 400, X-ray diffraction structure determination and analysis at 2.0 A resolution, molecular replacement
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crystal structure of Arabidopsis thaliana OPR3 in complex with 8-iso prostaglandin A1 (8-iso PGA1) is reported. The crystal structure is solved to 2.6 A. The positioning of 8-iso PGA1 reveals a new binding orientation for substrate in the active site that likely contributes to the relaxed stereospecificity observed for AtOPR3 relative to other OPR's
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one enzyme monomer per asymmetric unit, space group C2221. Enzyme is a member of an alpha/beta barrel fold family of FMN-containing oxidoreductases
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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construction of isozyme OPR3 mutant plants for subcellular localization study of the isozyme, overview
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
by affinity chromatography
by affinity chromatography
OPR1, OPR2 and OPR3
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recombinant isozyme OPR3 from Escherichia coli by nickel-imino-diacetic acid affinity chromatography
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recombinant tagged isozymes OPR1-3 from Escherichia coli by affinity chromatography
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
OPR DNA and amino acid sequence determination and analysis, comparative genomic analysis of OPR genes, phylogenetic analysis and sequence comparisons, detailed overview
overexpression of Arabidopsis OPR3 in hexaploid wheat (Triticum aestivum) alters plant development and freezing tolerance. Transgenic wheat plants with high AtOPR3 expression levels are characterized by delayed germination, slower growth, late flowering and senescence, and improved tolerance to short-term freezing
recombinant expression of OPR3 in Escherichia coli
cloning, and DNA sequence determination and analysis, expression of gene At2g06050, encoding isozyme OPR3, in Escherichia coli as N-terminally fusion protein fused to S-tag-His6-maltose binding protein
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enzyme cloned from its cDNA, open reading frame encodes a 372 amino acids polypeptide, functionally expressed in Escherichia coli
expression of the 3 isozymes OPR1-3 as N-terminally GST- or His-tagged enzymes in Escherichia coli
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OPR1 and OPR2, two closely related genes encodes 12-oxophytodienoic acid-10,11-reductases
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OPR3 expressed in functional form in Escherichia coli, cloning of OPR2 cDNA by reverse transcriptase-polymerase chain reaction, OPR2 expressed in insect cell cultures of Spodoptera frugiperda with transgenic Autographa californica baculoviruses and overexpressed in transgenic Arabidopsis thaliana
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recombinant expression in Escherichia coli, RNA interference is used to investigate the effect of knockdown expression of OPR1
recombinant expression in Escherichia coli, RNA interference is used to investigate the effect of knockdown expression of OPR2
subcloning of the OPR genes from a lambdaGEM11 genomic library
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
environmental protection
2,4,6-trinitrotoluene detoxofication, use of plants to remove environmental pollutants
environmental protection
2,4,6-trinitrotoluene detoxofication, use of plants to remove environmental pollutants
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Schaller, F.; Weiler, E.W.
Molecular cloning and characterization of 12-oxophytodienoate reductase, an enzyme of the octadecanoid signaling pathway from Arabidopsis thaliana. Structural and functional relationship to yeast old yellow enzyme
J. Biol. Chem.
272
28066-28072
1997
Arabidopsis thaliana (Q8LAH7), Arabidopsis thaliana, Capnoides sempervirens, Saccharomyces cerevisiae, Saccharomyces pastorianus
Manually annotated by BRENDA team
Schaller, F.; Hennig, P.; Weiler, E.W.
12-Oxophytodienoate-10,11-reductase: occurrence of two isoenzymes of different specificity against stereoisomers of 12-oxophytodienoic acid
Plant Physiol.
118
1345-1351
1998
Arabidopsis sp., Arabidopsis thaliana, Bryonia dioica, Capnoides sempervirens, Saccharomyces cerevisiae, Zea mays
Manually annotated by BRENDA team
Biesgen, C.; Weiler, E.
Structure and regulation of OPR1 and OPR2, two closely related genes encoding 12-oxophytodienoic acid-10,11-reductases from Arabidopsis thaliana
Planta
208
155-165
1999
Arabidopsis thaliana, Bryonia dioica
Manually annotated by BRENDA team
Costa, C.L.; Arruda, P.; Benedetti, C.E.
An Arabidopsis gene induced by wounding functionally homologous to flavoprotein oxidoreductases
Plant Mol. Biol.
44
61-71
2000
Arabidopsis sp., Arabidopsis thaliana, Capnoides sempervirens, Saccharomyces cerevisiae, Saccharomyces pastorianus, Zea mays
Manually annotated by BRENDA team
Schaller, F.; Biesgen, C.; Muessig, C.; Altmann, T.; Weiler, E.W.
12-Oxophytodienoate reductase 3 (OPR3) is the isoenzyme involved in jasmonate biosynthesis
Planta
210
979-984
2000
Arabidopsis thaliana, Capnoides sempervirens, Saccharomyces cerevisiae
Manually annotated by BRENDA team
Strassner, J.; Schaller, F.; Frick, U.B.; Howe, G.A.; Weiler, E.W.; Amrhein, N.; Macheroux, P.; Schaller, A.
Characterization and cDNA-microarray expression analysis of 12-oxophytodienoate reductases reveals differential roles for octadecanoid biosynthesis in the local versus the systemic wound response
Plant J.
32
585-601
2002
Arabidopsis thaliana, Solanum lycopersicum (Q9FEW9), Solanum lycopersicum (Q9FEX0), Solanum lycopersicum (Q9XG54)
Manually annotated by BRENDA team
Malone, T.E.; Madson, S.E.; Wrobel, R.L.; Jeon, W.B.; Rosenberg, N.S.; Johnson, K.A.; Bingman, C.A.; Smith, D.W.; Phillips, G.N., Jr.; Markley, J.L.; Fox, B.G.
X-ray structure of Arabidopsis At2g06050, 12-oxophytodienoate reductase isoform 3
Proteins
58
243-245
2004
Arabidopsis thaliana
Manually annotated by BRENDA team
Fox, B.G.; Malone, T.E.; Johnson, K.A.; Madson, S.E.; Aceti, D.; Bingman, C.A.; Blommel, P.G.; Buchan, B.; Burns, B.; Cao, J.; Cornilescu, C.; Doreleijers, J.; Ellefson, J.; Frederick, R.; Geetha, H.; Hruby, D.; Jeon, W.B.; Kimball, T.; Kunert, J.; Markley, J.L.; Newman, C.; Olson, A.; Peterson, F.C.; Phillips, G.N.; Primm, J.; Ramirez, B.; Rosenberg, N.S.; Runnels, M.; Seder, K.; Shaw, J.; Smith, D.W.; Sreenath, H.; Song, J.; Sussman, M.R.; Thao, S.; Troestler, D.; Tyler, E.; Tyler, R.; Ulrich, E.; Vinarov, D.; Vojtik, F.; Volkman, B.F.; Wesenberg, G.; Wrobel, R.L.; Zhang, J.; Zhao, Q.; Zolnai, Z.
X-ray structure of Arabidopsis At1g77680, 12-oxophytodienoate reductase isoform 1
Proteins
61
206-208
2005
Arabidopsis thaliana
Manually annotated by BRENDA team
Beynon, E.R.; Symons, Z.C.; Jackson, R.G.; Lorenz, A.; Rylott, E.L.; Bruce, N.C.
The role of oxophytodienoate reductases in the detoxification of the explosive 2,4,6-trinitrotoluene by Arabidopsis
Plant Physiol.
151
253-261
2009
Arabidopsis thaliana (Q8GYB8), Arabidopsis thaliana (Q8LAH7), Arabidopsis thaliana (Q9FUP0)
Manually annotated by BRENDA team
Li, W.; Liu, B.; Yu, L.; Feng, D.; Wang, H.; Wang, J.
Phylogenetic analysis, structural evolution and functional divergence of the 12-oxo-phytodienoate acid reductase gene family in plants
BMC Evol. Biol.
9
90
2009
Arabidopsis thaliana (Q9FUP0), Chlamydomonas reinhardtii, Medicago truncatula, Oryza sativa, Physcomitrium patens, Picea sitchensis, Populus trichocarpa, Selaginella moellendorffii, Sorghum bicolor, Volvox carteri, Zea mays
Manually annotated by BRENDA team
Han, B.; Malone, T.; Kim, D.; Bingman, C.; Kim, H.; Fox, B.; Phillips Jr., G.
Crystal structure of Arabidopsis thaliana 12-oxophytodienoate reductase isoform 3 in complex with 8-iso prostaglandin A 1
Proteins
79
3236-3241
2011
Arabidopsis thaliana
Manually annotated by BRENDA team
Pigolev, A.V.; Miroshnichenko, D.N.; Pushin, A.S.; Terentyev, V.V.; Boutanayev, A.M.; Dolgov, S.V.; Savchenko, T.V.
Overexpression of Arabidopsis OPR3 in hexaploid wheat (Triticum aestivum L.) alters plant development and freezing tolerance
Int. J. Mol. Sci.
19
3989
2018
Arabidopsis thaliana (Q9FUP0)
Manually annotated by BRENDA team
Maynard, D.; Kumar, V.; Sproi, J.; Dietz, K.J.
12-Oxophytodienoic acid reductase 3 (OPR3) functions as NADPH-dependent alpha,beta-ketoalkene reductase in detoxification and monodehydroascorbate reductase in redox homeostasis
Plant Cell Physiol.
61
584-595
2020
Arabidopsis thaliana (Q9FUP0)
Manually annotated by BRENDA team