Information on EC 1.14.13.21 - flavonoid 3'-monooxygenase

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The expected taxonomic range for this enzyme is: Magnoliophyta

EC NUMBER
COMMENTARY hide
1.14.13.21
-
RECOMMENDED NAME
GeneOntology No.
flavonoid 3'-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a flavonoid + NADPH + H+ + O2 = a 3'-hydroxyflavonoid + NADP+ + H2O
show the reaction diagram
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
(+)-dihydrokaempferol 3',5'-hydroxylase
-
-
Biosynthesis of secondary metabolites
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Flavone and flavonol biosynthesis
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Flavonoid biosynthesis
-
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flavonol biosynthesis
-
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leucodelphinidin biosynthesis
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leucopelargonidin and leucocyanidin biosynthesis
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luteolin biosynthesis
-
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Metabolic pathways
-
-
syringetin biosynthesis
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-
SYSTEMATIC NAME
IUBMB Comments
flavonoid,NADPH:oxygen oxidoreductase (3'-hydroxylating)
Acts on a number of flavonoids, including naringenin and dihydrokaempferol. Does not act on 4-coumarate or 4-coumaroyl-CoA.
CAS REGISTRY NUMBER
COMMENTARY hide
75991-44-5
-
85340-98-3
-
85340-98-3
oxygenase, flavonoid 3-mono-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
snapdragon
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
gene F3'H-1, two clones
SwissProt
Manually annotated by BRENDA team
line '01'
SwissProt
Manually annotated by BRENDA team
sweet orange
-
-
Manually annotated by BRENDA team
Columnea hybrida
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
japonica rice lines T65, T65-Plw (purple leaves), Nipponbare, Zhonghua 11, Tainong 67
-
-
Manually annotated by BRENDA team
cv. Bamba
SwissProt
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
parsley
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
syn. Rechsteineria
-
-
Manually annotated by BRENDA team
gene ght
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
two copies of the gene encoding the competing F3H enzyme are present in the grape genome, the second is transcriptionally silent
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
duplication of F3'H genes in plants, overview; duplication of F3'H genes in plants, overview; duplication of F3'H genes in plants, overview
metabolism
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
apiforol + NADPH + H+ + O2
luteoforol + NADP+ + H2O
show the reaction diagram
-
-
-
?
apigenin + NADPH + H+ + O2
luteolin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
apigenin + NADPH + O2
luteolin + NADP+ + H2O
show the reaction diagram
dihydrokaempferol + NADPH + H+ + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
dihydrokaempferol + O2 + 2-oxoglutarate
dihydroquercetin + succinate + CO2
show the reaction diagram
-
-
-
-
?
kaempferol + NADPH + H+ + O2
quercetin + NADP+ + H2O
show the reaction diagram
kaempferol + NADPH + O2
quercetin + NADP+ + H2O
show the reaction diagram
naringenin + NADPH + H+ + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
?
naringenin + NADPH + H+ + O2
eriodyctiol + NADP+ + H2O
show the reaction diagram
naringenin + NADPH + H+ + O2
eriodyctol + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
naringenin + O2 + 2-oxoglutarate
eriodictyol + succinate + CO2
show the reaction diagram
-
-
-
-
?
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
apigenin + NADPH + H+ + O2
luteolin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
apigenin + NADPH + O2
luteolin + NADP+ + H2O
show the reaction diagram
dihydrokaempferol + NADPH + H+ + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
dihydrokaempferol + O2 + 2-oxoglutarate
dihydroquercetin + succinate + CO2
show the reaction diagram
-
-
-
-
?
kaempferol + NADPH + H+ + O2
quercetin + NADP+ + H2O
show the reaction diagram
naringenin + NADPH + H+ + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
C5IGQ3, C5IGQ4, C5IGQ5
-
-
-
?
naringenin + NADPH + H+ + O2
eriodyctiol + NADP+ + H2O
show the reaction diagram
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
naringenin + O2 + 2-oxoglutarate
eriodictyol + succinate + CO2
show the reaction diagram
-
-
-
-
?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome
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a cytochrome P450 enzyme
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cytochrome P450
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe2+
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a cytochrome P450 enzyme
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
alpha,alpha'-dipyridyl
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partial
cytochrome c
diethyldicarbonate
FeCl3
-
-
ketoconazole
N-ethylmaleimide
p-chloromercuribenzoate
Tetcyclacis
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-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
N-ethylmaleimide
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1 mM: activation
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0001 - 0.048
apigenin
0.004 - 0.02
dihydrokaempferol
0.003 - 0.00715
kaempferol
0.0058
NADPH
Columnea hybrida
-
with kaempferol
0.0008 - 24
naringenin
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.000003
-
recombinant wild-type F3'H
additional information
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.8 - 8.4
-
half-maximal activity at pH 6.8 and 8.4
additional information
-
sharp drop in activity on either side of the optimum of pH 8.5
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
10 - 25
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10C: 30% of maximal activity, 25C: optimum
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.1
amino acid sequence calculation
9
-
calculatd
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
most active in developmental stages 2-5 of bud and flower formation
Manually annotated by BRENDA team
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-
Manually annotated by BRENDA team
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of immature seed coat
Manually annotated by BRENDA team
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enzyme is constitutively expressed in all tested tissues including fibrous roots, thick roots, storage roots, stems and leaves. During storage root formation, enzyme is expressed most abundantly in the storage roots
Manually annotated by BRENDA team
high level of F3'H expression; high level of F3'H expression; high level of F3'H expression; high level of F3'H expression
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0
-
addition of 14 mM mercaptoethanol, 15% sucrose, half-life 250 min
10
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addition of 14 mM mercaptoethanol, 15% sucrose, half-life 180 min
20
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addition of 14 mM mercaptoethanol, 15% sucrose, half-life 60 min
30
-
addition of 14 mM mercaptoethanol, 15% sucrose, half-life 24 min
100
-
10 min, activity destroyed
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
14 mM mercaptoethanol plus 15% sucrose stabilize, mercaptoethanol can be replaced by 1.4 mM dithiothreitol
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sucrose or glycerol plus dithiothreitol stabilize during purification and storage at -70C
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70C, storage of microsomes in presence of 14 mM mercaptoethanol and 15% sucrose, stable for several weeks
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-70C, sucrose or glycerol plus dithiothreitol stabilize during purification and storage
-
-80C, microsomal preparations containing 10% sucrose, frozen in liquid nitrogen, stable
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloning of coding sequence in over-expression vector, for complementation analysis Agrobacterium-mediated transformation of the plasmid into transparent testa Arabidopsis mutant tt7 (defective in flavonoid 3'-hydroxylase gene) leads to quercetin (3',4'-hydroxylated) accumulation, for yeast fusion enzyme interaction study PCR-amplification from cDNA, subcloned in pGADT7 fusion vector transformed in Saccharomyces cervisiae strains AH109 and Y187, pair-wise combination of fusion constructs by mating
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DNA and amino acid sequence determination and analysis, detailed phylogenetic analysis and comparison of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, overview
DNA and amino acid sequence determination and analysis, genetic mapping, phylogenetic analysis, expression analysis and metabolic profiling, phenotypes
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expression in Escherichia coli JM109
expression of wild-type enzyme and chimeric mutants in yeast strain INVSc 1 microsomes
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gene F3'H, DNA and amino acid sequence determination and analysis of wild-type and mutant genes, genomic organization, overview
gene F3'H, DNA and amino acid sequence determination and analysis, phylogenetic tree, developmental expression analysis, comparison of red and white cultivar enzyme expression levels, functional ectopic expression in Petunia hybrida altering flower color and flavonoid composition, overview
gene F3'H-1, two clones, DNA and amio acid sequence determination and analysis, sequence comparison, expression analysis, alternative polyadenylation in the 3'-UTR is adopted by this gene to generate heterogeneous transcripts, phylogenetic tree, functional expression of His-tagged F3'H-1 in Escherichia coli
gene F3'h1, DNA and amino acid sequence determination and analysis, genomic structure, expression pattern analysis; gene F3'h2, DNA and amino acid sequence determination and analysis, genomic structure, expression pattern analysis; gene F3'h3, DNA and amino acid sequence determination and analysis, genomic structure, expression pattern analysis; gene F3'h4, DNA and amino acid sequence determination and analysis, genomic structure, expression pattern analysis
gene F3'H1, DNA and amio acid sequence determination and analysis, phylogenetic tree; gene F3'H1, DNA and amio acid sequence determination and analysis, phylogenetic tree, overexpression of F3'H1 under control of the CaMV 35S promoter using the Agrobacterium tumefaciens transfection method; gene F3'H2, DNA and amino acid sequence determination and analysis, phylogenetic tree, overexpression of F3'H1 under control of the CaMV 35S promoter using the Agrobacterium tumefaciens transfection method
gene F3'h1, DNA, amino acid sequence, and promoter determination and analysis, the promoter region of the gene contains a putative G-box, two MYB-binding domains, and TA-repeats, the structure and number of the TA repeats is cultivar-dependent and highly polymorphic, the enzyme is encoded in the Tau locus involved in control of the pubescens and seed coat color, genetic structure and organization, dominant Tau and recessive tau allele of the locus produce tawny and gray pubescence, respectively, alleles at the locus are associated with chilling tolerance, overview
gene GmF3'H, DNA and amino acid sequence determination and analysis of 19 different cultivars, linked to the pleiotropic T locus and 2 recessive alleles, determination of the tissue expression pattern of gene GmF3'H
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gene MdF3'HI, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree, functional ectopic expression in Arabidopsis thaliana tt7 mutant and in Nicotiana tabacum; gene MdF3'HIIa, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree, functional ectopic expression in Arabidopsis thaliana tt7 mutant and in Nicotiana tabacum; gene MdF3'HIIb, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree, functional ectopic expression in Arabidopsis thaliana tt7 mutant and in Nicotiana tabacum
predominantly expressed in red form of plant
sf3'h1 gene, the enzyme is encoded at the T locus, quantitative expression analysis in wild-type and mutant plants
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two genes F3'H, DNA and amino acid sequence determination, genomic analysis and expression analysis in strain PN40024, phylogenetic tree, overview
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
drastic decline in expression during fruit ripening
ectopic expression of apple F3'H genes contributes to anthocyanin accumulation in the Arabidopsis thaliana transparent testa7-1 mutant tt7 grown under nitrogen stress, overview. Transgenic Arabidopsis tt7 seedlings xpressing apple F3'H regain red color pigmentation and significantly accumulate both 4'-hydroxylated pelargonidin and 3',4'-hydroxylated cyanidin; ectopic expression of apple F3'H genes contributes to anthocyanin accumulation in the Arabidopsis thaliana transparent testa7-1 mutant tt7 grown under nitrogen stress, overview. Transgenic Arabidopsis tt7 seedlings xpressing apple F3'H regain red color pigmentation and significantly accumulate both 4'-hydroxylated pelargonidin and 3',4'-hydroxylated cyanidin; ectopic expression of apple F3'H genes contributes to anthocyanin accumulation in the Arabidopsis thaliana transparent testa7-1 mutant tt7 grown under nitrogen stress, overview. Transgenic Arabidopsis tt7 seedlings xpressing apple F3'H regain red color pigmentation and significantly accumulate both 4'-hydroxylated pelargonidin and 3',4'-hydroxylated cyanidin
enzyme expression is under control of pericarp color1, P1
enzyme is highly expressed in all stages of fruit ripening
increase at stage of pigmentation initiation
light induced expression
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
T484F
-
site-directed mutagenesis, altered substrate specificity compared to the wild-type enzyme
T487A
-
site-directed mutagenesis, altered substrate specificity compared to the wild-type enzyme
T487S
-
site-directed mutagenesis, a conservative Thr to Ser exchange at position 487 conferred additional 5'-hydroxylation activity to recombinant Gerbera hybrida F3'H
Y484F/T487S
-
site-directed mutagenesis, altered substrate specificity compared to the wild-type enzyme
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
enzyme expression is under control of pericarp color1, P1. The P1 controlled 3-deoxyanthocyanidin and C-glycosyl flavone defence compounds accumulate at significantly higher levels in Pr1 silks as compared to pr1 silks. By virtue of increased maysin synthesis in Pr1 plants, corn ear worm larvae fed on Pr1/P1 silks show slower growth as compared to pr1/P1 silks
additional information
understanding the regulation of flavonoid hydroxylases could be used to modify flavonoid composition of fruits
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