Information on EC 1.3.1.45 - 2'-hydroxyisoflavone reductase

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The expected taxonomic range for this enzyme is: Spermatophyta

EC NUMBER
COMMENTARY hide
1.3.1.45
-
RECOMMENDED NAME
GeneOntology No.
2'-hydroxyisoflavone reductase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
vestitone + NADP+ = 2'-hydroxyformononetin + NADPH + H+
show the reaction diagram
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
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redox reaction
reduction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
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Isoflavonoid biosynthesis
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maackiain biosynthesis
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medicarpin biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
vestitone:NADP+ oxidoreductase
In the reverse reaction, a 2'-hydroxyisoflavone is reduced to an isoflavanone; 2'-hydroxypseudobaptigenin also acts. Involved in the biosynthesis of the pterocarpin phytoalexins medicarpin and maackiain.
CAS REGISTRY NUMBER
COMMENTARY hide
128449-69-4
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132264-36-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
chickpea
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-
Manually annotated by BRENDA team
variant Mundo Novo (IAC 388-17-1)
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
transgenic rice lines overexpressing the OsIRL gene under an abscisic acid inducible promoter are tolerant against methyl viologen (MV) and glucose/glucose oxidase-induced stress in rice leave and suspension-cultured cells
metabolism
FcIRL belongs to the class of pinoresinol-lariciresinol reductase, PRL, functioning in the biosynthesis of 8,8'-linked lignans, with function in catalyzing reduction of pinoresinol and lariciresinol into secoisolariciresinol, and medicinal secondary metabolism and resistance in Fagopyrum cymosum
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2',7-dihydroxy-3',4'-methylenedioxyisoflavone + NADPH
2',7-hydroxy-dihydro-3',4'-methylenedioxyisoflavone + NADP+
show the reaction diagram
2',7-dihydroxy-4',5'-methylenedioxyisoflavone + NADPH
(3R)2',7-dihydroxy-dihydro-4',5'-methylenedioxyisoflavone + NADP+
show the reaction diagram
2'-hydroxyformononetin + NADPH
(3R)-vestitone + NADP+
show the reaction diagram
2'-hydroxyformononetin + NADPH
vestitone + NADP+
show the reaction diagram
2'-hydroxyformononetin + NADPH + H+
vestitone + NADP+
show the reaction diagram
dehydrodiconiferyl alcohol + NADPH
isodihydrodehydrodiconiferyl alcohol NADP+
show the reaction diagram
-
-
-
?
isodihydrodehydrodiconiferyl alcohol + NADPH
tetrahydrodehydrodiconiferyl alcohol + NADP+
show the reaction diagram
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-
-
-
additional information
?
-
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
2'-hydroxyformononetin + NADPH
vestitone + NADP+
show the reaction diagram
2'-hydroxyformononetin + NADPH + H+
vestitone + NADP+
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
the enzyme sequence contains a conserved NmrA, nitrogen metabolite repression regulator, domain, V6-N244
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.013 - 0.0182
2'-Hydroxyformononetin
0.035
NADPH
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-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00383 - 0.215
2'-Hydroxyformononetin
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
a 5'-deletion to -404 completely abolishes promoter activation by abiotic stimulus in transgenic plants
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
35 - 40
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
constitutive expression
Manually annotated by BRENDA team
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constitutive expression
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
predicted from amino acid sequence
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
33280
calculated from cDNA
34000
predicted from nucleotide sequence encoding 314 amino acids
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
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gel filtration
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
the enzyme sequence contains one conserved glycosylation site at N214
phosphoprotein
the enzyme sequence contains multi-phosphorylation sites
additional information
the enzyme sequence contains an N-terminal acetylation site M1-K5
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
at 1.6 A resolution by hanging-drop vapor-diffusion method
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OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
complete inactivation without dithioerythritol in 6 h at 4°C
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390812
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 20 mM potassium phosphate buffer, pH 7.5, 1 mM dithioerythritol, 5% glycerol
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
as six-His tagged OsIRL protein, the generated recombinant OsIRL protein is used for antibody preparation
Ni2+-NTA affinity chromatography and gel filtration
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partially, subcellular fractions of cultured cells
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using Ni-NTA agarose affinity chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloning of full-length FcIRL, DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic analysis, overview
expression in Escherichia coli
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expression in Nicotiana tabacum
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expression in transgenic Nicotiana tabacum plants under control of the CaMV35S promotor
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gene constructs lacking the promoter of CaIRL are introduced into Agrobacterium tumefaciens strain LBA4404 and used to transform tobacco leaf discs
generating of transgenic rice lines overexpressing the OsIRL gene under an abscisic acid inducible promoter, the OsIRL transgenic rice line activated by abscisic acid treatment is tolerant against methyl viologen and glucose/glucose oxidase-induced stress in rice leaves and suspension-cultured cells, cloning of recombinant enzyme as six-His tagged OsIRL protein for antibody production
into Escherichia coli expression vector pET28a
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recombinantly expressed in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
After embedding of seeds in agar containing 2',7',-dichlorofluorescin, the H2O2 is highly stimulated in the elongation region compared with the root apex. The OsIRL mRNA expression level in 3-day-old roots is weakly expressed in the apex region, it shows an increment accompanying the increase in H2O2 concentration, results indicate that the expression level and localization of OsIRL is associated with H2O2 accumulation.; OsIRL gene and protein are downregulated in young seedling roots treated with diphenyleneiodonium, known quencher of reactive oxygen species, but to a lesser extent when compared with glutathione treatment in roots; OsIRL gene and protein are downregulated in young seedling roots treated with reduced glutathione, a known quencher of reactive oxygen species, in roots of 3 day-old young seedlings grown on glutathione, reactive oxygen species levels are significantly decreased by approximately 50% in the presence of 1 mM glutathione compared with untreated controls; OsIRL gene and protein are shown to be downregulated in young seedling roots treated with reduced glutathione and diphenyleneiodonium
increased expression of GbIRL1 is detected when the seedlings are treated with ultraviolet-B, 5-aminolevulinic acid, wounding and ethephon, abscisic acid, salicylic acid
OsIRL transcript level in rice suspension-cultured cells is found to be by hydrogen peroxide, ferric chloride, methyl viologen and glucose/glucose oxidase; the expression of OsIRL is slightly increased after treatment 0.02 mM abscisic acid in wild-type calli, suggesting a possible reason for glucose/glucose oxidase stress resistance; the OsIRL transcript level in rice suspension-cultured cells is induced by FeCl3 within 4 h after treatment, but down-regulated when co-treated with glutathione; the OsIRL transcript level in rice suspension-cultured cells is induced by glucose/glucose oxidase within 4 h after treatment, but down-regulated when co-treated with glutathione; the OsIRL transcript level in rice suspension-cultured cells is induced by methyl viologen within 4 h after treatment, but down-regulated when co-treated with glutathione; the OsIRL transcript level in rice suspension-cultured cells is induced by the oxidant H2O2, but down-regulated when co-treated with glutathione
the full-length version of the CaIRL promoter directs a reporter gene expression that is stimulated by mechanical injury as the expression from the native CaIRL gene; the promoter of a gene encoding an isoflavone reductase-like protein in coffee drives a stress-responsive expression in leaves; transcript level is markedly increased in response to fungal infection and mechanical injury, a rapid and marked increase in CaIRL expression is also observed following mechanical injury of the leaves (75fold after 4 h treatment), this induction is followed by a progressive decrease in transcript accumulation at 8 and 12 h post injury, the activation of CaIRL expression by mechanical injury is faster than that observed in response to fungal inoculation
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D285G
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decreased turnover rate
DELTA39-47
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nine of the amino acid residues around position 40 deleted in the current construct D39-47 IFR to facilitate crystallization, affects enzyme activity only slightly
G14F
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no detectable activity
H164A
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decreased turnover rate
K144A
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complete loss of enzyme activity
R97G
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decreased turnover rate
Y169A
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decreased turnover rate
Y272A
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decreased turnover rate