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Information on EC 1.1.1.234 - flavanone 4-reductase for references in articles please use BRENDA:EC1.1.1.234Word Map on EC 1.1.1.234
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The enzyme appears in viruses and cellular organisms
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(2S)-flavan-4-ol + NADP+ = (2S)-flavanone + NADPH + H+
(2S)-flavan-4-ol + NADP+ = (2S)-flavanone + NADPH + H+
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(2S)-flavan-4-ol + NADP+ = (2S)-flavanone + NADPH + H+
enzyme acts as flavone 4-reductase as well as dihydroflavonol 4-reductase
(2S)-flavan-4-ol + NADP+ = (2S)-flavanone + NADPH + H+
enzyme acts as flavone 4-reductase as well as dihydroflavonol 4-reductase
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(2S)-flavan-4-ol + NADP+ = (2S)-flavanone + NADPH + H+
enzyme acts as flavone 4-reductase as well as dihydroflavonol 4-reductase
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apigeninidin 5-O-glucoside biosynthesis
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luteolinidin 5-O-glucoside biosynthesis
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Flavonoid biosynthesis
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(2S)-flavan-4-ol:NADP+ 4-oxidoreductase
Involved in the biosynthesis of 3-deoxyanthocyanidins from flavanones such as naringenin or eriodictyol.
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3-deoxyanthocyanidin synthase
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Columnea hybrida
strain 'Heklua'
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brenda
Columnea hybrida Heklua
strain 'Heklua'
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strains M9 and Weirouge
SwissProt
brenda
strains Pyrodwarf, Conference and Abbe Fetel
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brenda
gene SmDFR
UniProt
brenda
syn. Rechsteineria cardinalis, strain ' Feuerschein'
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brenda
strains: Peterson Ac 1355 A-D (sm), al-line, and Pirat
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brenda
cultivars #7, M36001, and Nakei
UniProt
brenda
purple Nakei-MS3B (PP) and tan Greenleaf (pp) cultivars
UniProt
brenda
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evolution
the enzyme belongs to the plant DFR superfamily, phylogenetic analysis
malfunction
Sorghums with a tan injury response have non-functional FNR alleles (p). The FNR gene of cultivar M36001 has an insertion in the coding region. Sorghums with a tan injury response have lower levels of flavan-4-ols (precursors of apigeninidin and luteolinidin-apiforol and luteoforol, respectively) than do sorghums with a purple or red injury response and are unable to synthesize 3-deoxyanthocyanidins
additional information
homology modeling on the basis of the crystal structure of grape dihydroflavonol 4-reductase, PDB ID 3C1T
metabolism
the DFR gene is a key gene late in the flavonoid biosynthesis pathway, overview. The enzyme posesses flavanone 4-reductase activity and also is a key enzyme in the biosynthesis of anthocyanidins, proanthocyanidins, and other flavonoids
metabolism
the enzyme, encoded by gene Sb06g029550, is involved in the 3-deoxyanthocyanidin synthesis pathway
physiological function
the enzyme is of importance in plant development
physiological function
the enzyme is responsible for the synthesis of 3-deoxyanthocyanidins. The variation of purple-red-orange is explained by the balance of two 3-deoxyanthocyanidins, uteolinidin and apigeninidin. The balance is controlled by the expression level of flavonoid 3'-hydroxylase (F3'H), which encodes a protein that hydroxylates the 3' position of the B-ring of naringenin to produce a precursor of luteolinidin
physiological function
upon wounding or pathogen invasion, leaves of Sorghum bicolor plants with the P gene turn purple, whereas leaves with the recessive allele turn brown or tan. This purple phenotype is determined by the production of two 3-deoxyanthocyanidins, apigeninidin and luteolinidin, which are not produced by the tan-phenotype plants
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(2S)-eriodictyol + NADPH
luteoforol + NADP+
(2S)-eriodictyol + NADPH + H+
luteoforol + NADP+
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-
-
?
(2S)-flavan-4-ol + NADP+
(2S)-flavanone + NADPH + H+
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-
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
(2S)-naringenin + NADPH + H+
apiforol + NADP+
5,7,3',4',5'-pentahydroxyflavanone + NADPH
5,7,3',4',5'-pentahydroxyflavan-4-ol + NADP+
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-
-
?
eriodictyol + NADP+
luteoforol + NADPH + H+
naringenin + NADPH + H+
apiforol + NADP+
additional information
?
-
(2S)-eriodictyol + NADPH
luteoforol + NADP+
Columnea hybrida
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-
-
?
(2S)-eriodictyol + NADPH
luteoforol + NADP+
Columnea hybrida Heklua
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-
-
?
(2S)-eriodictyol + NADPH
luteoforol + NADP+
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-
-
?
(2S)-eriodictyol + NADPH
luteoforol + NADP+
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
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?
(2S)-eriodictyol + NADPH
luteoforol + NADP+
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-
-
-
?
(2S)-eriodictyol + NADPH
luteoforol + NADP+
-
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
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?
(2S)-eriodictyol + NADPH
luteoforol + NADP+
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-
-
?
(2S)-eriodictyol + NADPH
luteoforol + NADP+
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-
-
?
(2S)-eriodictyol + NADPH
luteoforol + NADP+
-
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
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-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
Columnea hybrida
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involved in the biosynthesis of 3-deoxyanthocyanidines such as apigeninidin or luteolinidin, from (2S)-flavanones naringenin or eriodictyol
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?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
Columnea hybrida Heklua
-
involved in the biosynthesis of 3-deoxyanthocyanidines such as apigeninidin or luteolinidin, from (2S)-flavanones naringenin or eriodictyol
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?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
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-
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
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-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
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-
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
-
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
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-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
-
involved in the biosynthesis of 3-deoxyanthocyanidines such as apigeninidin or luteolinidin, from (2S)-flavanones naringenin or eriodictyol
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?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
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-
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
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reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
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-
?
(2S)-naringenin + NADPH + H+
apiforol + NADP+
Columnea hybrida
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?
(2S)-naringenin + NADPH + H+
apiforol + NADP+
Columnea hybrida Heklua
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?
(2S)-naringenin + NADPH + H+
apiforol + NADP+
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-
?
(2S)-naringenin + NADPH + H+
apiforol + NADP+
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?
(2S)-naringenin + NADPH + H+
apiforol + NADP+
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?
(2S)-naringenin + NADPH + H+
apiforol + NADP+
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?
(2S)-naringenin + NADPH + H+
apiforol + NADP+
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reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
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?
eriodictyol + NADP+
luteoforol + NADPH + H+
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?
eriodictyol + NADP+
luteoforol + NADPH + H+
recombinant Sb06g029550 protein
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?
naringenin + NADPH + H+
apiforol + NADP+
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?
naringenin + NADPH + H+
apiforol + NADP+
recombinant Sb06g029550 protein
apiforol is converted to apigeninidin with Nar + protein + HCl treatment
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?
additional information
?
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the enzyme also catalyzes the reduction of dihydroflavonols to leucoanthocyanins, SmDFR can readily reduce dihydroquercetin and dihydrokampferol, as a dihydroflavonol 4-reductase, DFR, EC 1.1.1.219, but it cannot reduce dihydromyricetin
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additional information
?
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the enzyme also catalyzes the reduction of dihydroflavonols to leucoanthocyanins, SmDFR can readily reduce dihydroquercetin and dihydrokampferol, as a dihydroflavonol 4-reductase, DFR, EC 1.1.1.219, but it cannot reduce dihydromyricetin
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additional information
?
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as dihydroxyflavonols, such as dihydrokaempferol, dihydroquercetin and dihydromyricetin are substrates for the Sinningia enzyme preparation, too, the enzyme might be identical with dihydroflavonol-4-reductase
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additional information
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enzyme FNR converts flavanones to flavan-4-ols
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additional information
?
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the reaction mixtures are acid-treated to convert the direct reaction products, flavan-3,4-diol, and flavan-4-ol, to their respective anthocyanidin or 3-deoxyanthocyanidins, and analyzed by LC-MS/MS
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additional information
?
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enzyme also acts on 5-deoxydihydroflavonols
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(2S)-eriodictyol + NADPH
luteoforol + NADP+
(2S)-flavan-4-ol + NADP+
(2S)-flavanone + NADPH + H+
C5YGL7
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-
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
(2S)-naringenin + NADPH + H+
apiforol + NADP+
eriodictyol + NADP+
luteoforol + NADPH + H+
C5YGL7
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-
?
naringenin + NADPH + H+
apiforol + NADP+
C5YGL7
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?
additional information
?
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(2S)-eriodictyol + NADPH
luteoforol + NADP+
Q9XES5
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
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?
(2S)-eriodictyol + NADPH
luteoforol + NADP+
-
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
-
?
(2S)-eriodictyol + NADPH
luteoforol + NADP+
-
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
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-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
Columnea hybrida
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involved in the biosynthesis of 3-deoxyanthocyanidines such as apigeninidin or luteolinidin, from (2S)-flavanones naringenin or eriodictyol
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
Columnea hybrida Heklua
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involved in the biosynthesis of 3-deoxyanthocyanidines such as apigeninidin or luteolinidin, from (2S)-flavanones naringenin or eriodictyol
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?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
Q9XES5
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
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-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
-
reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
-
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
-
involved in the biosynthesis of 3-deoxyanthocyanidines such as apigeninidin or luteolinidin, from (2S)-flavanones naringenin or eriodictyol
-
?
(2S)-flavanone + NADPH
(2S)-flavan-4-ol + NADP+
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reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
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-
?
(2S)-naringenin + NADPH + H+
apiforol + NADP+
Q9XES5
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-
?
(2S)-naringenin + NADPH + H+
apiforol + NADP+
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-
-
?
(2S)-naringenin + NADPH + H+
apiforol + NADP+
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reaction provides precursors for the synthesis of 3-deoxyanthocyanidins
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?
additional information
?
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A5Z0G1
the enzyme also catalyzes the reduction of dihydroflavonols to leucoanthocyanins, SmDFR can readily reduce dihydroquercetin and dihydrokampferol, as a dihydroflavonol 4-reductase, DFR, EC 1.1.1.219, but it cannot reduce dihydromyricetin
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additional information
?
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the enzyme also catalyzes the reduction of dihydroflavonols to leucoanthocyanins, SmDFR can readily reduce dihydroquercetin and dihydrokampferol, as a dihydroflavonol 4-reductase, DFR, EC 1.1.1.219, but it cannot reduce dihydromyricetin
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additional information
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no cofactors are FAD, FMN or tetrahydropterin, with or without NADPH
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NADH
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77% as active as NADPH
NADH
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can partially replace for NADPH
NADPH
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required
NADPH
Columnea hybrida
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required
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1,10-phenanthroline
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slight inhibition at 1 mM, 50-70% inhibition at 5 mM
glycerol
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10% v/v, complete irreversible inactivation
naringenin
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above 0.1 mM
p-chloromercuribenzoate
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0.5 mM
p-hydroxymercuribenzoate
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complete inhibition at 1 mM
Sucrose
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20% w/v, complete irreversible inactivation
additional information
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no inhibition by KCN, EDTA, diethyl dithiocarbamate, phenanthroline or N-ethylmaleimide, 2 mM each
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0.021 - 0.023
(2S)-naringenin
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0.0009
Columnea hybrida
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6
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4.7 - 6.9
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about half-maximal activity at pH 4.7 and 6.9
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25
native enzyme
40
recombinant enzyme from yeast
40
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recombinant enzyme from yeast
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a red callus line
brenda
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brenda
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brenda
Columnea hybrida
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brenda
Columnea hybrida Heklua
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brenda
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brenda
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brenda
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brenda
-
low activity
brenda
-
brenda
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brenda
additional information
expression level of SmDFR is higher in flowers compared with both leaves and roots
brenda
additional information
-
expression level of SmDFR is higher in flowers compared with both leaves and roots
brenda
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Columnea hybrida
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brenda
Columnea hybrida Heklua
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brenda
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E1C9L4
Mycobacterium thermoresistibile;
Plasmodium vivax (strain Salvador I);
P22290
Plasmodium vivax (strain Salvador I);
P22290
Plasmodium vivax (strain Salvador I);
P22290
Plasmodium vivax (strain Salvador I);
P22290
Plasmodium vivax (strain Salvador I);
P22290
Plasmodium vivax (strain Salvador I);
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?
x * 40000, recombinant His-tagged enzyme, SDS-PAGE, x * 37800, about, sequence calculation
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freezing fresh flowers in liquid nitrogen and storing them at -80°C enhances extractable activity compared to fresh flowers
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recombinant His-tagged enzyme from Escherichia coli strain BL21 Star(DE3)pLysS by nickel affinity chromatography
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expressed in yeast and petunia
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expressed in yeast strain InvSc1
gene P or Sb06g029550, genetic structure, quantitative RT-PCR enzyme expression analysis
gene P or Sb06g029550, quantitative RT-PCR enzyme expression analysis, genetic mapping, phylogenetic analysis and tree, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21 Star(DE3)pLysS
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
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the enzyme is highly induced by cutting stress
the enzyme is highly induced by wounding and pathogen invasion, analysis of 3-deoxyanthocyanidin accumulation
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C252Y
cultivar Greenleaf Sb06g029550 has a point mutation that causes the amino acid change
additional information
expression of both flavone synthase II (FNSII) and flavonoid 3'-hydroxylase (F3'H) leads to the synthesis of apigenin and luteolin in cultivar #7, and expression of both flavanone 4-reductase and F3'H leads to the synthesis of 3-deoxyanthocyanidins in cultivar Nakei-MS3B
additional information
analysis of Sb06g029550 in four sorghum accessions with the tan phenotype, overview
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DFRA_ANTMA
446
49633
Swiss-Prot
DFRA_ARATH
382
42775
Swiss-Prot
DFRA_CALCH
364
40726
Swiss-Prot
DFRA_DIACA
360
40430
Swiss-Prot
DFRA_GERHY
366
41102
Swiss-Prot
DFRA_HORVU
354
38435
Swiss-Prot
DFRA_MAIZE
357
38856
Swiss-Prot
DFRA_MALDO
348
39030
Swiss-Prot
DFRA_MEDSA
217
24389
Swiss-Prot
DFRA_PETHY
380
42435
Swiss-Prot
DFRA_PYRCO
347
38934
Swiss-Prot
DFRA_SOLLC
379
42429
Swiss-Prot
DFRA_VITVI
337
37757
Swiss-Prot
A0A2P6PQ57_ROSCH
403
43941
TrEMBL
A0A2I0A6C5_9ASPA
325
36452
TrEMBL
A0A087CHN5_9BIFI
360
38542
TrEMBL
C5YGL7_SORBI
344
37796
TrEMBL
A5Z0G1_SAUME
342
38648
TrEMBL
PVDR_PLAVS
1070
119683
Swiss-Prot
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Stich, K.; Forkmann, G.
Biosynthesis of 3-deoxyanthocyanins with flower extracts from Sinningia cardinalis
Biochemistry
27
785-789
1988
Sinningia cardinalis
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brenda
Stich, K.; Forkmann, G.
Studies on columnidin biosynthesis with flower extracts from Columnea hybrida
Z. Naturforsch. C
43
311-314
1988
Columnea hybrida, Columnea hybrida Heklua
-
brenda
Fischer, T.C.; Halbwirth, H.; Meisel, B.; Stich, K.; Forkmann, G.
Molecular cloning, substrate specificity of the functionally expressed dihydroflavonol 4-reductases from Malus domestica and Pyrus communis cultivars and the consequences for flavonoid metabolism
Arch. Biochem. Biophys.
412
223-230
2003
Malus domestica, Malus domestica (Q9XES5), Pyrus communis
brenda
Halbwirth, H.; Martnes, S.; Wienand, U.; Forkmann, G.; Stich, K.
Biochemical formation of anthocyanins in silk tissue of Zea mays
Plant Sci.
164
489-495
2003
Zea mays
-
brenda
Li, H.; Qiu, J.; Chen, F.; Lv, X.; Fu, C.; Zhao, D.; Hua, X.; Zhao, Q.
Molecular characterization and expression analysis of dihydroflavonol 4-reductase (DFR) gene in Saussurea medusa
Mol. Biol. Rep.
39
2991-2999
2012
Saussurea medusa (A5Z0G1), Saussurea medusa
brenda
Mizuno, H.; Yazawa, T.; Kasuga, S.; Sawada, Y.; Kanamori, H.; Ogo, Y.; Hirai, M.Y.; Matsumoto, T.; Kawahigashi, H.
Expression of flavone synthase II and flavonoid 3'-hydroxylase is associated with color variation in tan-colored injured leaves of Sorghum
Front. Plant Sci.
7
1718
2016
Sorghum bicolor (C5YGL7)
brenda
Kawahigashi, H.; Kasuga, S.; Sawada, Y.; Yonemaru, J.; Ando, T.; Kanamori, H.; Wu, J.; Mizuno, H.; Momma, M.; Fujimoto, Z.; Hirai, M.Y.; Matsumoto, T.
The sorghum gene for leaf color changes upon wounding (P) encodes a flavanone 4-reductase in the 3-deoxyanthocyanidin biosynthesis pathway
G3 (Bethesda)
6
1439-1447
2016
Sorghum bicolor (C5YGL7)
brenda
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