Information on EC 1.14.13.103 - 8-dimethylallylnaringenin 2'-hydroxylase

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The expected taxonomic range for this enzyme is: Sophora flavescens

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EC NUMBER
COMMENTARY hide
1.14.13.103
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RECOMMENDED NAME
GeneOntology No.
8-dimethylallylnaringenin 2'-hydroxylase
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REACTION
REACTION DIAGRAM
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ORGANISM
UNIPROT
LITERATURE
sophoraflavanone B + NADPH + H+ + O2 = leachianone G + NADP+ + H2O
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
sophoraflavanone G biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
sophoraflavanone-B,NADPH:oxygen oxidoreductase (2'-hydroxylating)
A membrane-bound cytochrome P-450 heme-thiolate monooxygenase that is associated with the endoplasmic reticulum [1,2]. This enzyme is specific for sophoraflavanone B as substrate. NADPH cannot be replaced by NADH, FAD or FMN. Along with EC 2.5.1.70 (naringenin 8-dimethylallyltransferase) and EC 2.5.1.71 (leachianone G 2''-dimethylallyltransferase), this enzyme forms part of the sophoraflavanone-G-biosynthesis pathway.
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CAS REGISTRY NUMBER
COMMENTARY hide
400886-31-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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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)-8-dimethylallylnaringenin + NADPH + H+ + O2
leachianone G + NADP+ + H2O
show the reaction diagram
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i.e. sophoraflavanone B, the enzyme catalyzes the 2'-hydroxylation of 8-DMAN and is O2-dependent
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8-dimethylallylnaringenin + NADPH + H+ + O2
leachianone G + NADP+ + H2O
show the reaction diagram
additional information
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the enzyme is a cytochrome P450 monooxygenase
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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
8-dimethylallylnaringenin + NADPH + H+ + O2
leachianone G + NADP+ + H2O
show the reaction diagram
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the enzyme is crucial for lavandulylated flavanone formation, the enzyme catalyzes the 2'-hydroxylation of 8-DMAN, which is then formed to sophoraflavanone G, pathway overview
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
additional information
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the enzyme is a cytochrome P450 monooxygenase
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
carbon monoxide
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cytochrome c
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70% inhibition at 10 mM
Metyrapone
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34% inhibition at 1 mM
miconazole
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36% inhibition at 1 mM
tropolon
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30% inhibition at 1 mM
additional information
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no or poor inhibition by ancymidol and KCN
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.055
8-dimethylallylnaringenin
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0.034
NADPH
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pH OPTIMUM
ORGANISM
UNIPROT
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LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
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assay at
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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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the enzyme is tightly bound to the membrane
Manually annotated by BRENDA team
additional information
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subcellular localization of the enzymes involved in the biosynthetic route from naringenin to sophoraflavanone G, overview
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Manually annotated by BRENDA team
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme partially by microsome preparation
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.103)
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)