Information on EC 1.14.13.136 - 2-hydroxyisoflavanone synthase

Word Map on EC 1.14.13.136
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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
1.14.13.136
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RECOMMENDED NAME
GeneOntology No.
2-hydroxyisoflavanone synthase
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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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-
-
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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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-
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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.
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
no activity in Arabidopsis thaliana
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-
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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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
-
-
-
-
?
(2S)-liquiritigenin + O2 + NADPH + H+
2,7,4'-trihydroxyisoflavanone + NADP+ + H2O
show the reaction diagram
-
-
-
?
(2S)-naringenin + O2 + NADPH + H+
2,5,7,4'-tetrahydroxyisoflavanone + NADP+ + H2O
show the reaction diagram
-
-
-
?
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)
-
?
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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-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Iron
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the (P450) enzyme contains iron
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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
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.006 - 0.011
7,4'-dihydroxyflavanone
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
59400
x * 59400, SDS-PAGE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 59400, SDS-PAGE
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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
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.136)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)