Information on EC 1.14.14.89 - 4'-methoxyisoflavone 2'-hydroxylase

for references in articles please use BRENDA:EC1.14.14.89
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.14.14.89
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RECOMMENDED NAME
GeneOntology No.
4'-methoxyisoflavone 2'-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
formononetin + [reduced NADPH-hemoprotein reductase] + O2 = 2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydroxylation
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oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
(-)-maackiain biosynthesis
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(-)-medicarpin biosynthesis
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Isoflavonoid biosynthesis
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
formononetin,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (2'-hydroxylating)
A heme-thiolate protein (P-450). Acts on isoflavones with a 4'-methoxy group, such as formononetin and biochanin A. Involved in the biosynthesis of the pterocarpin phytoalexins medicarpin and maackiain. EC 1.14.13.89, isoflavone 2'-hydroxylase, is less specific and acts on other isoflavones as well as 4'-methoxyisoflavones.
CAS REGISTRY NUMBER
COMMENTARY hide
110183-49-8
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Mervill cv. Harosoy 63, elicitor-induced
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Manually annotated by BRENDA team
elicitor-induced
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
biochanin A + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxybiochanin A + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
daidzein + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxydaidzein + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
genistein + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxygenistein + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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
daidzein + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxydaidzein + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
A0A0U1WKA6
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-
?
formononetin + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
genistein + [reduced NADPH-hemoprotein reductase] + O2
2'-hydroxygenistein + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
A0A0U1WKA6
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P-450
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NADPH-hemoprotein reductase
A flavoprotein containing both FMN and FAD. This enzyme catalyses the transfer of electrons from NADPH, an obligatory two-electron donor, to microsomal P-450 monooxygenases, EC 1.14.14._
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additional information
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no cofactors are FAD and FMN
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mn2+
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cells treated with MnCl2 exhibit 5fold activity after 12 hours
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
BAS 110
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BAS 111
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CO
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ratio CO:O2 of 9:1 leads to 88-96% inhibition
cytochrome c
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0.01 mM cytochrome c reduces activity to 14%, 0.1 mM cytochrome c reduces activity to 4%
juglone
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0.001 mM juglone reduces activity to 50%
ketoconazol
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tetcyclasis
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Triadimefone
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additional information
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no inhibition by 5 mM KCN and 1 mM EDTA
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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cells susceptible to Ascochyta rabiei can be elicitor-induced to 500% activity
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
13
Biochanin A
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3.3
formononetin
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
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assay conditions
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 100 mM potassium phosphate, pH 7.5 containing 400 mM sucrose and 3.5 mM 2-mercaptoethanol, 24 h
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Saccharomyces cerevisae
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expressed in Saccharomyces cerevisae overexpressing CYP81E1
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gene dgr, recombinant enzyme expression in Escherichia coli strain BL21(DE3), aerobic bioconversion capacity of the recombinant Escherichia coli whole-cell under the optimized conditions, method evaluation and optimization, overview
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
reduction of soy isoflavones by use of Escherichia coli whole-cell biocatalyst expressing isoflavone reductase under aerobic conditions, optimization of the aerobic bioconversion conditions, overview. Addition of chloramphenicol significantly increases the bioconversion capacity of the recombinant Escherichia coli whole-cell, but addition of chloramphenicol does not increase the expression of S-DGR irrespective of whether the concentration of chloramphenicol is high. The maximal concentration of daidzein that the recombinant Escherichia coli whole-cell is able to convert efficiently is 0.8 mmol/l. The average bioconversion rate for daidzein is 85.0% and the yield of 2'-hydroxydaidzein is 0.545 mmol/l