Information on EC 1.1.1.219 - dihydrokaempferol 4-reductase

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The expected taxonomic range for this enzyme is: Spermatophyta

EC NUMBER
COMMENTARY hide
1.1.1.219
-
RECOMMENDED NAME
GeneOntology No.
dihydrokaempferol 4-reductase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
cis-3,4-leucopelargonidin + NADP+ = (+)-dihydrokaempferol + NADPH + H+
show the reaction diagram
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
redox reaction
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-
-
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reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
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Flavonoid biosynthesis
-
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leucodelphinidin biosynthesis
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leucopelargonidin and leucocyanidin biosynthesis
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
cis-3,4-leucopelargonidin:NADP+ 4-oxidoreductase
Also acts, in the reverse direction, on (+)-dihydroquercetin and (+)-dihydromyricetin; each dihydroflavonol is reduced to the corresponding cis-flavan-3,4-diol. NAD+ can act instead of NADP+, but more slowly. Involved in the biosynthesis of anthocyanidins in plants.
CAS REGISTRY NUMBER
COMMENTARY hide
83682-99-9
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98668-58-7
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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-
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Manually annotated by BRENDA team
line N89-53 and line YN01-429 (a yellow-seeded canola-quality germplasm)
-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
chinese cabbage
UniProt
Manually annotated by BRENDA team
line 101
SwissProt
Manually annotated by BRENDA team
Camellia sinensis (L.) O. Kuntze
-
UniProt
Manually annotated by BRENDA team
Citrus sinensis (L.) Osbeck, cultivars Tarocco, Navel and Ovale
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-
Manually annotated by BRENDA team
cv.'kumotoshi', japanese cedar
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-
Manually annotated by BRENDA team
Tanga
SwissProt
Manually annotated by BRENDA team
v. Terra Regina
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
hybrid, cv. Star Gazer
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
no activity in Escherichia coli
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-
-
Manually annotated by BRENDA team
no activity in Nicotiana tabacum
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-
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Manually annotated by BRENDA team
no activity in Saccharomyces cerevisiae
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-
-
Manually annotated by BRENDA team
sainfoin, cv. Melrose
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-
Manually annotated by BRENDA team
douglas fir
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-
Manually annotated by BRENDA team
Kardinal
SwissProt
Manually annotated by BRENDA team
gene SmDFR; putative
UniProt
Manually annotated by BRENDA team
line 19
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
the enzyme belongs to the plant DFR superfamily, phylogenetic analysis
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
(+)-2,3-dihydrokaempferol + NADPH
cis-3,4-leucopelargonidin + NADP+
show the reaction diagram
(+)-dihydrokaempferol + NADPH
cis-3,4-leucopelargonidin + NADP+
show the reaction diagram
(+)-dihydrokaempferol + NADPH + H+
cis-3,4-leucopelargonidin + NADP+
show the reaction diagram
-
-
-
?
(+)-dihydromyricetin + NADPH
cis-3,4-leucodelphinidin + NADP+
show the reaction diagram
(+)-dihydroquercetin + NADPH
cis-3,4-leucocyanidin + NADP+
show the reaction diagram
(+)-dihydroquercetin + NADPH + H+
cis-3,4-leucocyanidin + NADP+
show the reaction diagram
(+/-)-fustin + NADPH
?
show the reaction diagram
preference for (-)-isomer
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-
?
(+/-)-taxifolin + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
(-)-fustin + NADPH
?
show the reaction diagram
stereospecific for (-)-isomer
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-
?
(2R,3R)-(+)-dihydrokaempferol + NADPH
(2R,3S,4S)-cis-3,4-leucopelargonidin + NADP+
show the reaction diagram
(2R,3R)-dihydromyricetin + NADPH
(2R,3S,4R)-cis-3,4-leucodelphinidin + NADP+
show the reaction diagram
(2R,3R)-dihydroquercetin + NADPH
(2R,3S,4R)-leucocyanidin + NADP+
show the reaction diagram
2,3-dihydromyricetin + NADPH
cis-3,4-leucodelphinidin + NADP+
show the reaction diagram
low activity
-
-
?
2,3-dihydroquercetin + NADPH
cis-3,4-leucocyanidin + NADP+
show the reaction diagram
i.e. (+)-taxifolin, stereospecific for (+)-isomer
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-
?
2,3-dihydrorobinetin + NADPH
?
show the reaction diagram
-
-
-
?
7-hydroxyflavanone + NADPH + H+
2,4-cis-7-hydroxyflavan-4-ol + 2,4-trans-7-hydroxyflavan-4-ol + NADP+
show the reaction diagram
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-
-
?
dihydroflavonol + NADPH
flavan-3,4-diol + NADP+
show the reaction diagram
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-
-
-
?
dihydrokaempferol + NADPH
cis-3,4-leucopelargonidin + NADP+
show the reaction diagram
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-
-
-
r
dihydrokaempferol + NADPH + H+
leucopelargonidin + NADP+
show the reaction diagram
dihydromyricetin + NADPH
cis-3,4-leucodelphinidin + NADP+
show the reaction diagram
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-
-
-
?
dihydromyricetin + NADPH
leucodelphinidin + NADP+
show the reaction diagram
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-
-
-
r
dihydromyricetin + NADPH + H+
leucodelphinidin + NADP+
show the reaction diagram
dihydroquercetin + NADPH
?
show the reaction diagram
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assay at 25C, pH 7.5
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-
?
dihydroquercetin + NADPH
cis-3,4-leucocyanidin + NADP+
show the reaction diagram
dihydroquercetin + NADPH
leucocyanidin + NADP+
show the reaction diagram
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-
-
-
r
dihydroquercetin + NADPH + H+
leucocyanidin + NADP+
show the reaction diagram
eriodictyol + NADPH + H+
luteoforol + NADP+
show the reaction diagram
naringenin + NADPH + H+
apiferol + NADP+
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
dihydrokaempferol + NADPH
cis-3,4-leucopelargonidin + NADP+
show the reaction diagram
-
-
-
-
r
dihydromyricetin + NADPH
leucodelphinidin + NADP+
show the reaction diagram
-
-
-
-
r
dihydroquercetin + NADPH
leucocyanidin + NADP+
show the reaction diagram
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-
-
-
r
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
abscisic acid
decreases expression
Cu2+
-
strong inhibitor
diethyldithiocarbamate
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50% inhibition at 2 mM
dithiothreitol
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50% inhibition at 5 mM
iodoacetate
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to some extent
myricetin
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flavonol that can be an inhibitor of the activity of DFR towards dihydroflavonols
quercetin
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flavonol that can be an inhibitor of the activity of DFR towards dihydroflavonols
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
S-methyl 1,2,3-benzothiadiazole-7-carbothioate
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treatment of fruits
additional information
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enzyme expression is increased with time during a 24 h exposure to UV-A irradiation, but not by irradiation with red, blue, UV-B, and a combination of blue with red light
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.037 - 0.048
(+)-dihydroquercetin
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.000012
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pigmented cultivar Tarocco in 0.05 M Tris-HCl pH 7.5, l M dihydroquercetin, 2 mM NADPH, 1 U glucose-6-phosphate dehydrogenase, 6 mM glucose-6-phosphate and enzyme extract at 25C
0.00002
with dihydrokaempferol as substrate
0.0003
with dihydrokaempferol as substrate; with naringenin as substrate
0.0004
with dihydrokaempferol as substrate; with naringenin as substrate
0.0005
with naringenin as substrate
0.0006
0.0007
0.0008
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with eriodictyol as substrate
0.0012
0.0013
0.0014
0.0015
with dihydromyricetin as substrate
0.014
with dihydrokaempferol as substrate
0.021
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with dihydrokaempferol as substrate
0.024
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-
0.042
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sample callus control in 25 mM Tris-HCl (pH 7.0), 4 mM NADPH and 0.1 mM dihydroquercetin at 25C
0.103
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sample callus L-1 in 25 mM Tris-HCl (pH 7.0), 4 mM NADPH and 0.1 mM dihydroquercetin at 25C
0.155
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sample callus L-2 in 25 mM Tris-HCl (pH 7.0), 4 mM NADPH and 0.1 mM dihydroquercetin at 25C
0.202
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sample plant control in 25 mM Tris-HCl (pH 7.0), 4 mM NADPH and 0.1 mM dihydroquercetin at 25C
0.268
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sample plant L-2 in 25 mM Tris-HCl (pH 7.0), 4 mM NADPH and 0.1 mM dihydroquercetin at 25C
0.349
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sample plant L-1 in 25 mM Tris-HCl (pH 7.0), 4 mM NADPH and 0.1 mM dihydroquercetin at 25C
156.4
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without any fruit treatment, day 4 of storage at 1C
42850
recombinant protein
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 6.5
-
broad optimum
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.1 - 7.2
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about half-maximal activity at pH 5.1 and 7.2
6 - 7
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maximum DFR activities achieved towards dihydroflavonols and flavanones
6 - 7.5
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6.4 - 8
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no significant variations in activity
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25 - 30
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maximum DFR activities achieved towards dihydroflavonols and flavanones
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.22
sequence analysis
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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flavanone 3-hydroxylase, dihydroflavonol 4-reductase and flavonoid 3',5'-hydrolase are expressed in progeny with colored tuber skin, while dihydroflavonol 4-reductase and flavonoid 3',5'-hydrolase are not expressed, and flavanone 3-hydroxylase is only weakly expressed, in progeny with white tuber skin. Expression is regulated by transcription factor Stan2
Manually annotated by BRENDA team
isoform PtrDFR2 transcripts are more than twice as abundant as isoform DFR1 in young petioles and 15 times more abundant in old petioles
Manually annotated by BRENDA team
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DFR activity is lower in YN01-429 as compared to N89-53 seed coats. Two copies of the DFR gene, which are both functional in YN01-429, homeoallelic repression or silencing, together they show very low expression levels (17fold fewer transcripts) relative to DFR acitvity in N89-53 seed coats
Manually annotated by BRENDA team
mRNA accumulation of DFR is higher in the shoots than in the leaves
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
33500
-
his-tagged DFR4b, SDS-PAGE
36600
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his-tagged DFR4a, SDS-PAGE
38010
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calculated from sequence of cDNA
38670
sequence analysis
39900
-
his-tagged DFR2, SDS-PAGE
40000
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his-tagged DFR3, SDS-PAGE
40300
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his-tagged DFR1, SDS-PAGE; his-tagged DFR5, SDS-PAGE
133000
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gel filtration with Sephadex G-150
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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3D structure of the ternary complex, overview
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DFR-NADP+-flavonol (myricetin and quercetin) complexes, at room temperature, by hanging-drop vapour diffusion method. Complex DFR-NADP+-myricetin belongs to space group P21 (unit-cell parameters a = 47.23, b = 177.96, c = 92.60 A, beta = 104.8). Complex DFR-NADP+-quercetin belongs to space group P6122 (unit-cell parameters a = b = 174.94, c = 290.18 A)
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purified recombinant enzyme in complex with NADPH and dihydroquercetin, X-ray diffraction structure determination and analysis at 1.8 A resolution
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, 20% loss of activity within 2 days, 2-mercaptoethanol protects
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-20C, 57% loss of activity after 4 months, 2-mercaptoethanol protects
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-70C, 10% glycerol, crude extract stable for several weeks
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1C, after 4 days of storage decrease in enzyme activity
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5C, stable for 36 h
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
70% saturated ammonium sulfate precipitation and dialysis
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recombinanet enzyme from Escherichia coli
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
allele of DFR associated with red color, under the control of a doubled CaMV 35S promoter and tobacco etch virus translational enhancer introduced into the potato cultivar Prince Hairy (genotype dddd rrrr P-), which has white tubers and pale blue flowers
DFR2, DFR3 and DFR5 were expressed in Escherichia coli
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enzyme expression analysis under UV-light irradiation, overview
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Escherichia coli strains transformed with plasmid pTrcHis2-DFR to only express DFR. Escherichia coli strains harboring plasmid pET-DFR-LAR expressing DFR and leucoanthocyanidin reductase
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expression in Escherichia coli
-
expression in Escherichia coli JM109
expression in Escherichia coli; into expression vector pQE-30 UA, and transformed into Escherichia coli M15 pREP-4 competent cells
expression in Nicotiana tabacum; expression in Nicotiana tabacum
expression in Saccharomyces cerevisiae; gene SmDFR, DNA and amino acid sequence determination and analysis, phylogenetic analysis, quantitative real-time PCR expression analysis, functional expression in Saccharomyces cerevisiae strain INV Sc1
functional expression in tobacco protoplasts via electroporation, subcloning and overexpression in Escherichia coli strain GI724 and in Saccharomyces cerevisiae strain INV Sc1, the recombinant Escherichia coli strain shows no enzyme activity
into pTrcHis2-TOPO and heterologously expressed in Escherichia coli TOP10F' strain. DFR cDNA cloned into pRSF-FHT and inserted into Escherichia coli BL21Star to create E-color strain
isozyme MtDFR1, from a young seed cDNA library, functional expression in Escherichia coli; isozyme MtDFR2, from a young seed cDNA library, functional expression in Escherichia coli
overexpression in Escherichia coli strain GI724 and in Saccharomyces cerevisiae strain INV Sc1
vector pC1-DFR overexpressed in transgenic tobacco plants, having distinctive petal colors, showing some variation in their intensity
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
decrease at stage of pigmentation inititation
expression is down-regulated in response to drought stress and abscisic acid, and unaffected by gibberellic acid treatment
Camellia sinensis (L.) O. Kuntze
-
-
expression is down-regulated in response to drought stress and abscisic acid, and unaffected by gibberellic acid treatment; in response to drought stress
expression is up-regulated in response to wounding, with concomitant modulation of catechins content
Camellia sinensis (L.) O. Kuntze
-
-
expression is up-regulated in response to wounding, with concomitant modulation of catechins content; in response to wounding, with concomitant modulation of catechins content. Expression is maximum in younger rather than older leaves
flavanone 3-hydroxylase, dihydroflavonol 4-reductase and flavonoid 3',5'-hydrolase are expressed in progeny with colored tuber skin, while dihydroflavonol 4-reductase and flavonoid 3',5'-hydrolase are not expressed, and flavanone 3-hydroxylase is only weakly expressed, in progeny with white tuber skin. Expression is regulated by transcription factor Stan2
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
N133D
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site-directed mutagenesis,
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
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