Information on EC 1.14.13.136 - 2-hydroxyisoflavanone synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.13.136
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RECOMMENDED NAME
GeneOntology No.
2-hydroxyisoflavanone synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(2S)-naringenin + O2 + NADPH + H+ = 2,4',5,7-tetrahydroxyisoflavanone + H2O + NADP+
show the reaction diagram
(2)
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liquiritigenin + O2 + NADPH + H+ = 2,4',7-trihydroxyisoflavanone + H2O + NADP+
show the reaction diagram
(1)
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
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Isoflavonoid biosynthesis
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isoflavonoid biosynthesis I
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isoflavonoid biosynthesis II
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SYSTEMATIC NAME
IUBMB Comments
liquiritigenin,NADPH:oxygen oxidoreductase (hydroxylating, aryl migration)
Requires cytochrome P-450. The reaction involves the migration of the 2-phenyl group of the flavanone to the 3-position of the isoflavanone. The 2-hydroxyl group is derived from the oxygen molecule. EC 4.2.1.105, 2-hydroxyisoflavanone dehydratase, acts on the products with loss of water and formation of genistein and daidzein, respectively.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
no activity in Arabidopsis thaliana
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Manually annotated by BRENDA team
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UniProt
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
(2S)-7,4'-dihydroxyflavanone + O2 + NADPH + H+
2,7,4'-trihydroxyisoflavanone + H2O + NADP+
show the reaction diagram
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i.e. (2S)-liquiritigenin
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-
?
(2S)-liquiritigenin + O2 + NADPH + H+
2,7,4'-trihydroxyisoflavanone + H2O + NADP+
show the reaction diagram
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?
(2S)-liquiritigenin + O2 + NADPH + H+
2,7,4'-trihydroxyisoflavanone + NADP+ + H2O
show the reaction diagram
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-
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?
(2S)-naringenin + O2 + NADPH + H+
2,5,7,4'-tetrahydroxyisoflavanone + NADP+ + H2O
show the reaction diagram
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?
7,4'-dihydroxyflavanone + O2 + NADPH + H+
2,7,4'-trihydroxyisoflavanone + 3,7,4'-trihydroxyflavanone + H2O + NADP+
show the reaction diagram
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i.e. liquirtigenin
3,7,4'-trihydroxyflavanone is the by-product of the reaction (8% yield)
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?
liquiritigenin + O2 + NADPH + H+
2,7,4'-trihydroxyisoflavanone + H2O + NADP+
show the reaction diagram
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major product is 2,7,4'-trihydroxyisoflavanone which further reacts to daidzein
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?
additional information
?
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the enzyme also produces a spirodienone intermediate from (2S)-liquiritigenin which further reacts to 2,7-dihydroxy-4'-methoxyisoflavanone and formononetin
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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
(2S)-liquiritigenin + O2 + NADPH + H+
2,7,4'-trihydroxyisoflavanone + NADP+ + H2O
show the reaction diagram
Q7XAU5
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?
(2S)-naringenin + O2 + NADPH + H+
2,5,7,4'-tetrahydroxyisoflavanone + NADP+ + H2O
show the reaction diagram
Q7XAU5
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?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Iron
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the (P450) enzyme contains iron
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ancymidol
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complete inhibition at 1 mM
CO2
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52% inhibition in the presence of CO2 gas
Metyrapone
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complete inhibition at 0.1 mM
SKF 525-A
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73% inhibition at 2 mM
uniconazole
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complete inhibition at 0.1 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.006 - 0.011
7,4'-dihydroxyflavanone
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
59400
x * 59400, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 59400, SDS-PAGE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Arabidopsis thaliana and in leaves of Nicotiana benthamiana
expressed in Saccharomyces cerevisiae microsomes
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expressed in Saccharomyces cerevisiae strain BJ2168
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
K375T
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the mutant catalyses the aryl migration from liquiritigenin to yield 3,7,4'-trihydroxyflavanone only, its pH optimum is at pH 6.5
L371V
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inactive
L371V/K375T
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the mutant shows 3-5% activity levels compared to the wild type. The mutant produces a mixture of 95% 3beta-hydroxyflavanone and 5% flavone from (2S)-liquiritigenin
S310T
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the mutant also catalyses the aryl migration from liquiritigenin to yield 2,7,4'-trihydroxyisoflavanone, but the ratio of the by-product (3,7,4'-trihydroxyflavanone) formation is increased from 8% to 36% (pH 7.5), and a small amount (7%) of a new product, 7,4'-dihydroxyflavone, is detected compared to the wild type
S310T/K375T
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the P450 level of the mutant is approximately 1.5times that of wild type. The mutant shows 3-5% activity levels compared to the wild type
S310T/L371V/K375T
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the mutant produces 100% flavone from (2S)-liquiritigenin; the mutant shows 4times higher P450 level than the wild type