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Enzyme Nomenclature
Information on EC 1.14.13.88 - flavanoid 3',5'-hydroxylase
Word Map on EC 1.14.13.88
- 1.14.13.88
-
anthocyanins
-
3'-hydroxylase
- petal
- delphinidin
- dihydroflavonols
-
berry
-
4-reductase
- flavonols
- petunia
- cyanidin
-
b-ring
-
grapevine
- hybrida
- carnation
-
flavan-3-ols
- pelargonidin
-
red-skinned
- dihydrokaempferol
-
bluish
- gentian
- malvidin
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.14.13.88
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RECOMMENDED NAME
GeneOntology No.
flavanoid 3',5'-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a 3'-hydroxyflavanone + NADPH + H+ + O2 = a 3',5'-dihydroxyflavanone + NADP+ + H2O
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a flavanone + NADPH + H+ + O2 = a 3'-hydroxyflavanone + NADP+ + H2O
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
flavanone,NADPH:oxygen oxidoreductase
A heme-thiolate protein (P-450). The 3',5'-dihydroxyflavanone is formed via the 3'-hydroxyflavanone. In Petunia hybrida the enzyme acts on naringenin, eriodictyol, dihydroquercetin (taxifolin) and dihydrokaempferol (aromadendrin). The enzyme catalyses the hydroxylation of 5,7,4'-trihydroxyflavanone (naringenin) at either the 3' position to form eriodictyol or at both the 3' and 5' positions to form 5,7,3',4',5'-pentahydroxyflavanone (dihydrotricetin). The enzyme also catalyses the hydroxylation of 3,5,7,3',4'-pentahydroxyflavanone (taxifolin) at the 5' position, forming ampelopsin. NADH is not a good substitute for NADPH.
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CAS REGISTRY NUMBER
COMMENTARY
94047-23-1
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Met210 genetic variant with light purple flowers; w1 allele, Val210 genetic variant with white flowers
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Gentiana triflora x Gentiana scabra cultivar Albireo, ornamental gentian plant
UniProt
diploid potato clone W5281.2, female parent/purple tuber skin/genotype Ii RR Pp
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fragment; cv. red cultivar Cabernet Sauvignon
SwissProt
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
physiological function
pigment accumulation in the base of column of Dendrobium moniliforme is due to the preferential expression of the enzyme. The lack of colors in perianths is at least due to transcriptional control of the enzyme
additional information
metabolism
essential in gentiodelphin (delphinidin 3-O-glucosyl-5-O-caffeoyl-glucosyl-3'-O-caffeoyl-glucoside) biosynthesis via flavonoid production causing the flower color of petals
metabolism
flavonoid biosynthesis, the relative expression of flavonoid 3'5' hydroxylase and similar genes compared to leucoanthocyanidin reductase correspond to seasonal expression balances
metabolism
the F3'5'H is a key enzyme of the phenylpropanoid pathway
additional information
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comparison of genetic variants and and Clark w1: flower petals of B09121 contain lower amounts of four major anthocyanins, i.e. malvidin 3,5-di-O-glucoside, petunidin 3,5-di-O-glucoside, delphinidin 3,5-di-O-glucoside and delphinidin 3-O-glucoside, common in purple flowers and contain small amounts of the 5'-unsubstituted versions of the above anthocyanins, peonidin 3,5-di-O-glucoside, cyanidin 3,5-di-O-glucoside and cyanidin 3-O-glucoside, suggesting that F3'5'H activity is reduced and flavonoid 3'-hydroxylase, EC 1.14.13.21, activity is increased compared to Clark w1 plants
additional information
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comparison of genetic variants and and Clark w1: flower petals of B09121 contain lower amounts of four major anthocyanins, i.e. malvidin 3,5-di-O-glucoside, petunidin 3,5-di-O-glucoside, delphinidin 3,5-di-O-glucoside and delphinidin 3-O-glucoside, common in purple flowers and contain small amounts of the 5'-unsubstituted versions of the above anthocyanins, peonidin 3,5-di-O-glucoside, cyanidin 3,5-di-O-glucoside and cyanidin 3-O-glucoside, suggesting that F3'5'H activity is reduced and flavonoid 3'-hydroxylase, EC 1.14.13.21, activity is increased compared to Clark w1 plants
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additional information
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comparison of genetic variants and and Clark w1: flower petals of B09121 contain lower amounts of four major anthocyanins, i.e. malvidin 3,5-di-O-glucoside, petunidin 3,5-di-O-glucoside, delphinidin 3,5-di-O-glucoside and delphinidin 3-O-glucoside, common in purple flowers and contain small amounts of the 5'-unsubstituted versions of the above anthocyanins, peonidin 3,5-di-O-glucoside, cyanidin 3,5-di-O-glucoside and cyanidin 3-O-glucoside, suggesting that F3'5'H activity is reduced and flavonoid 3'-hydroxylase, EC 1.14.13.21, activity is increased compared to Clark w1 plants
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2S)-naringenin + 2 NADPH + 2 H+ + 2 O2
5,7,3',4',5'-pentahydroxyflavanone + 2 NADP+ + 2 H2O
5,7,3',4'-tetrahydroxyflavanone + NADPH + H+ + O2
5,7,3',4',5'-pentahydroxyflavanone + NADP+ + H2O
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-
-
-
?
5,7,4'-trihydroxyflavanone + NADPH + H+ + O2
5,7,3',4'-tetrahydroxyflavanone + NADP+ + H2O
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-
-
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?
dihydrokaempferol + NADPH + O2
3',5'-dihydroxy-dihydrokaempferol + NADP+ + H2O
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?
dihydrokaempherol + NADPH + H+ + O2
dihydromyricetin + NADP+ + H2O
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-
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?
dihydroquercetin + NADPH + H+ + O2
5'-hydroxyquercetin + NADP+ + H2O
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-
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?
dihydroquercetin + NADPH + O2
5'-hydroxy-dihydroquercetin + NADP+ + H2O
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?
naringenin + 2 NADPH + 2 H+ + 2 O2
5,7,3',4',5'-pentahydroxyflavanone + 2 NADP+ + 2 H2O
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-
-
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?
naringenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavanone + NADPH + H2O
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?
(2S)-naringenin + 2 NADPH + 2 H+ + 2 O2
5,7,3',4',5'-pentahydroxyflavanone + 2 NADP+ + 2 H2O
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?
(2S)-naringenin + 2 NADPH + 2 H+ + 2 O2
5,7,3',4',5'-pentahydroxyflavanone + 2 NADP+ + 2 H2O
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?
(2S)-naringenin + 2 NADPH + 2 H+ + 2 O2
5,7,3',4',5'-pentahydroxyflavanone + 2 NADP+ + 2 H2O
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-
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?
(2S)-naringenin + 2 NADPH + 2 H+ + 2 O2
5,7,3',4',5'-pentahydroxyflavanone + 2 NADP+ + 2 H2O
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-
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?
(2S)-naringenin + 2 NADPH + 2 H+ + 2 O2
5,7,3',4',5'-pentahydroxyflavanone + 2 NADP+ + 2 H2O
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-
-
?
(2S)-naringenin + 2 NADPH + 2 H+ + 2 O2
5,7,3',4',5'-pentahydroxyflavanone + 2 NADP+ + 2 H2O
-
-
-
?
(2S)-naringenin + 2 NADPH + 2 H+ + 2 O2
5,7,3',4',5'-pentahydroxyflavanone + 2 NADP+ + 2 H2O
Nierembergia sp.
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-
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?
(2S)-naringenin + 2 NADPH + 2 H+ + 2 O2
5,7,3',4',5'-pentahydroxyflavanone + 2 NADP+ + 2 H2O
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?
(2S)-naringenin + 2 NADPH + 2 H+ + 2 O2
5,7,3',4',5'-pentahydroxyflavanone + 2 NADP+ + 2 H2O
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?
(2S)-naringenin + 2 NADPH + 2 H+ + 2 O2
5,7,3',4',5'-pentahydroxyflavanone + 2 NADP+ + 2 H2O
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-
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?
(2S)-naringenin + 2 NADPH + 2 H+ + 2 O2
5,7,3',4',5'-pentahydroxyflavanone + 2 NADP+ + 2 H2O
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?
(2S)-naringenin + 2 NADPH + 2 H+ + 2 O2
5,7,3',4',5'-pentahydroxyflavanone + 2 NADP+ + 2 H2O
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?
(2S)-naringenin + 2 NADPH + 2 H+ + 2 O2
5,7,3',4',5'-pentahydroxyflavanone + 2 NADP+ + 2 H2O
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?
(2S)-naringenin + 2 NADPH + 2 H+ + 2 O2
5,7,3',4',5'-pentahydroxyflavanone + 2 NADP+ + 2 H2O
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-
-
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?
apigenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
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?
apigenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
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?
apigenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
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?
apigenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
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-
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?
apigenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
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-
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?
apigenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
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-
-
?
apigenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
Nierembergia sp.
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-
-
?
apigenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
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-
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?
apigenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
-
-
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?
apigenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
-
-
-
-
?
apigenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
-
-
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?
apigenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
-
-
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?
apigenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
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-
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?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
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?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
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-
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?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
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-
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?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
-
-
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?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
-
-
-
?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
-
-
-
?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
Nierembergia sp.
-
-
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?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
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-
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?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
-
-
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?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
-
-
-
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?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
-
-
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?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
-
-
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?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
-
-
-
?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
-
-
-
-
?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
-
-
-
?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
-
-
-
?
dihydrokaempferol + NADPH + H+ + O2
dihydromyricetin + NADP+ + H2O
-
-
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?
dihydrokaempferol + NADPH + H+ + O2
dihydromyricetin + NADP+ + H2O
-
-
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?
dihydrokaempferol + NADPH + H+ + O2
dihydromyricetin + NADP+ + H2O
preferred substrate of the wild-type enzyme
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-
?
dihydrokaempferol + NADPH + H+ + O2
dihydromyricetin + NADP+ + H2O
Viola sp.
-
leads to synthesis of delphinidin
-
-
?
kaempferol + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
-
-
-
?
kaempferol + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
-
-
-
?
kaempferol + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
-
-
-
?
kaempferol + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
-
-
-
?
kaempferol + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
-
-
-
?
kaempferol + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
-
-
-
?
kaempferol + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
Nierembergia sp.
-
-
-
?
kaempferol + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
-
-
-
?
kaempferol + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
-
-
-
?
kaempferol + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
-
-
-
-
?
kaempferol + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
-
-
-
?
kaempferol + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
-
-
-
?
kaempferol + NADPH + O2
5,7,3',4',5'-pentahydroxyflavone + NADP+ + H2O
-
-
-
?
naringenin + 2 NADPH + 2 H+ + 2 O2
pentahydroxyflavanone + 2 NADP+ + 2 H2O
-
-
-
?
naringenin + 2 NADPH + 2 H+ + 2 O2
pentahydroxyflavanone + 2 NADP+ + 2 H2O
-
-
-
?
naringenin + 2 NADPH + 2 H+ + 2 O2
pentahydroxyflavanone + 2 NADP+ + 2 H2O
-
-
-
-
?
naringenin + NADPH + H+ + O2
3'-hydroxynaringenin + NADP+ + H2O
-
-
-
?
naringenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavanone + NADP+ + H2O
-
-
-
?
naringenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavanone + NADP+ + H2O
-
-
-
?
additional information
?
-
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
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-
-
additional information
?
-
the enzyme hydroxylates a broad range of flavonoid substrates in vitro, 3',5'-hydroxylation, 3',4'-hydroxylation and 3',4',5'-hydroxylation occurs, overview
-
-
-
additional information
?
-
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
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-
-
additional information
?
-
the enzyme hydroxylates a broad range of flavonoid substrates in vitro, 3',5'-hydroxylation, 3',4'-hydroxylation and 3',4',5'-hydroxylation occurs, overview
-
-
-
additional information
?
-
-
key enzyme in the synthesis of 3',5'-hydroxylated anthocyanins, which are generally required for blue or purple flowers
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-
-
additional information
?
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key enzyme in the synthesis of 3',5'-hydroxylated anthocyanins, which are generally required for blue or purple flowers
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-
additional information
?
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the enzyme is the key enzyme for delphinidin biosynthesis in the flavonoid biosynthetic pathway, biosynthesis of colour pigments, overview
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-
additional information
?
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the enzyme is the key enzyme for delphinidin biosynthesis in the flavonoid biosynthetic pathway, biosynthesis of colour pigments, overview
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-
additional information
?
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the enzyme is the key enzyme for delphinidin biosynthesis in the flavonoid biosynthetic pathway, biosynthesis of colour pigments, overview
-
-
-
additional information
?
-
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
the enzyme hydroxylates a broad range of flavonoid substrates in vitro, 3',5'-hydroxylation, 3',4'-hydroxylation and 3',4',5'-hydroxylation occurs, overview
-
-
-
additional information
?
-
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
the enzyme hydroxylates a broad range of flavonoid substrates in vitro, 3',5'-hydroxylation, 3',4'-hydroxylation and 3',4',5'-hydroxylation occurs, overview
-
-
-
additional information
?
-
the enzyme hydroxylates a broad range of flavonoid substrates in vitro, overview
-
-
-
additional information
?
-
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
the enzyme hydroxylates a broad range of flavonoid substrates in vitro, 3',5'-hydroxylation, 3',4'-hydroxylation and 3',4',5'-hydroxylation occurs, overview
-
-
-
additional information
?
-
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
the enzyme hydroxylates a broad range of flavonoid substrates in vitro, 3',5'-hydroxylation, 3',4'-hydroxylation and 3',4',5'-hydroxylation occurs, overview
-
-
-
additional information
?
-
Nierembergia sp.
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
Nierembergia sp.
the enzyme hydroxylates a broad range of flavonoid substrates in vitro, 3',5'-hydroxylation, 3',4'-hydroxylation and 3',4',5'-hydroxylation occurs, overview
-
-
-
additional information
?
-
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
the enzyme hydroxylates a broad range of flavonoid substrates in vitro, 3',5'-hydroxylation, 3',4'-hydroxylation and 3',4',5'-hydroxylation occurs, overview
-
-
-
additional information
?
-
substrate specificity of F3'H and the F3'5'H, flavonoid 3',5'-hydroxylase, EC 1.14.13.88, evolutionary derived from F3'H, is determined near the N-terminal end and the functional difference between these two enzymes near the C-terminal end, relatively few amino acids exchanges are required for the evolutionary extension of 3'- to 3',5'-hydroxylation activity, overview
-
-
-
additional information
?
-
the enzyme is involved in biosynthesis of delphinidin-derived anthocyanins which are responsible for the rose to lilac flower colours of the petals, overview
-
-
-
additional information
?
-
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
the enzyme hydroxylates a broad range of flavonoid substrates in vitro, 3',5'-hydroxylation, 3',4'-hydroxylation and 3',4',5'-hydroxylation occurs, overview
-
-
-
additional information
?
-
-
the enzyme catalyzes the 3',5'-hydroxylation of dihydroflavonols, the precursors of purple anthocyanins
-
-
-
additional information
?
-
key enzyme in the synthesis of 3',5'-hydroxylated anthocyanins, which are generally required for blue or purple flowers
-
-
-
additional information
?
-
-
key enzyme in the synthesis of 3',5'-hydroxylated anthocyanins, which are generally required for the expression of blue or purple flower color. Pigment composition analysis of transgenic plants suggests that the F3'5'H transgene not only creates or inhibits the biosynthetic pathway to 3',5'-hydroxylated anthocyanins but switches the pathway to 3',5'-hydroxylated or 3'-hydroxylated anthocyanins
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-
-
additional information
?
-
-
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
-
the enzyme hydroxylates a broad range of flavonoid substrates in vitro, 3',5'-hydroxylation, 3',4'-hydroxylation and 3',4',5'-hydroxylation occurs, overview
-
-
-
additional information
?
-
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
the enzyme hydroxylates a broad range of flavonoid substrates in vitro, 3',5'-hydroxylation, 3',4'-hydroxylation and 3',4',5'-hydroxylation occurs, overview
-
-
-
additional information
?
-
-
enzyme is involved in anthocyanin biosynthesis. When expressed as a transgene in the red-skinned cultivar Desiree changes tuber skin color from red to purple
-
-
-
additional information
?
-
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
the enzyme hydroxylates a broad range of flavonoid substrates in vitro, 3',5'-hydroxylation, 3',4'-hydroxylation and 3',4',5'-hydroxylation occurs, overview
-
-
-
additional information
?
-
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
the enzyme hydroxylates a broad range of flavonoid substrates in vitro, 3',5'-hydroxylation, 3',4'-hydroxylation and 3',4',5'-hydroxylation occurs, overview
-
-
-
additional information
?
-
-
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
-
the enzyme hydroxylates a broad range of flavonoid substrates in vitro, overview
-
-
-
additional information
?
-
the enzyme is involved in the biosynthetic pathway of delphinidin-based anthocyanins, as well as of the flavonols quercetin and myricetin and procyanidin and prodelphinidin, correlation of enzyme expression pattern and flavonoid composition, flavonoid composition in organs of Vitis vinifera, flavonoid biosynthetic pathways, overview
-
-
-
additional information
?
-
the enzyme plays a role in the phenyl-propanoid pathway and the biosynthesis of cyanidin- and delphinidin-based anthocyanin pigments in the socalled red cultivars of grapevine, metabolic profiling and colour variations, overview, the enzyme is responsible for flavonoid accumulation in tissues
-
-
-
additional information
?
-
the enzyme plays a role in the phenyl-propanoid pathway and the biosynthesis of cyanidin- and delphinidin-based anthocyanin pigments in the socalled red cultivars of grapevine, metabolic profiling and colour variations, overview, the enzyme is responsible for flavonoid accumulation in tissues
-
-
-
additional information
?
-
the enzyme plays a role in the phenyl-propanoid pathway and the biosynthesis of cyanidin- and delphinidin-based anthocyanin pigments in the socalled red cultivars of grapevine, metabolic profiling and colour variations, overview, the enzyme is responsible for flavonoid accumulation in tissues
-
-
-
additional information
?
-
the enzyme plays a role in the phenyl-propanoid pathway and the biosynthesis of cyanidin- and delphinidin-based anthocyanin pigments in the socalled red cultivars of grapevine, metabolic profiling and colour variations, overview, the enzyme is responsible for flavonoid accumulation in tissues
-
-
-
additional information
?
-
the enzyme plays a role in the phenyl-propanoid pathway and the biosynthesis of cyanidin- and delphinidin-based anthocyanin pigments in the socalled red cultivars of grapevine, metabolic profiling and colour variations, overview, the enzyme is responsible for flavonoid accumulation in tissues
-
-
-
additional information
?
-
transcriptional regulation of the enzyme in fruits, the enzyme is expressed after flowering, when proanthocyanidins are synthesized, accumulation of hydroxylated anthocyaniins in grape berries, flavonoid biosynthetic pathways, overview
-
-
-
additional information
?
-
-
flavonoid pathway during berry development, anthocyanin synthesis takes place mainly in postveraison, detailed overview, metabolite and expression profiling
-
-
-
additional information
?
-
-
the enzyme is a key enzyme in colour variation of the grape berry conforming to a peculiar pattern of genotype-specific expression of the whole set of anthocyanin genes in a direct transcript-metabolite phenotype relationship, the enzyme is involved in anthocyanin composition, colour intensity and colour hue of grapes at berry maturity, overview
-
-
-
additional information
?
-
-
the hydroxylase is responsible for the hydroxylation of the 5' position on the B ring of the flavonoid skeleton
-
-
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
dihydrokaempferol + NADPH + O2
3',5'-dihydroxy-dihydrokaempferol + NADP+ + H2O
Q2PWV0, Q2PWV1, Q2PWV2, Q2PWV3, Q2PWV4
-
-
-
?
dihydrokaempherol + NADPH + H+ + O2
dihydromyricetin + NADP+ + H2O
C6L1M3
-
-
-
?
dihydroquercetin + NADPH + O2
5'-hydroxy-dihydroquercetin + NADP+ + H2O
Q2PWV0, Q2PWV1, Q2PWV2, Q2PWV3, Q2PWV4
-
-
-
?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
Q2UYU7
-
-
-
?
dihydrokaempferol + 2 NADPH + 2 H+ + 2 O2
dihydromyricetin + 2 NADP+ + 2 H2O
Q3C210
-
-
-
?
dihydrokaempferol + NADPH + H+ + O2
dihydromyricetin + NADP+ + H2O
Q304Q4
-
-
-
?
dihydrokaempferol + NADPH + H+ + O2
dihydromyricetin + NADP+ + H2O
Viola sp.
-
leads to synthesis of delphinidin
-
-
?
naringenin + 2 NADPH + 2 H+ + 2 O2
pentahydroxyflavanone + 2 NADP+ + 2 H2O
C6L1M3
-
-
-
?
naringenin + 2 NADPH + 2 H+ + 2 O2
pentahydroxyflavanone + 2 NADP+ + 2 H2O
Q304Q4
-
-
-
?
naringenin + 2 NADPH + 2 H+ + 2 O2
pentahydroxyflavanone + 2 NADP+ + 2 H2O
-
-
-
-
?
naringenin + NADPH + H+ + O2
3'-hydroxynaringenin + NADP+ + H2O
Q304Q4
-
-
-
?
naringenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavanone + NADP+ + H2O
Q2UYU7
-
-
-
?
naringenin + NADPH + O2
5,7,3',4',5'-pentahydroxyflavanone + NADP+ + H2O
Q3C210
-
-
-
?
additional information
?
-
Q9FPN4
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
Q52YL8
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
-
key enzyme in the synthesis of 3',5'-hydroxylated anthocyanins, which are generally required for blue or purple flowers
-
-
-
additional information
?
-
O04790
key enzyme in the synthesis of 3',5'-hydroxylated anthocyanins, which are generally required for blue or purple flowers
-
-
-
additional information
?
-
-
the enzyme is the key enzyme for delphinidin biosynthesis in the flavonoid biosynthetic pathway, biosynthesis of colour pigments, overview
-
-
-
additional information
?
-
Q25C80
the enzyme is the key enzyme for delphinidin biosynthesis in the flavonoid biosynthetic pathway, biosynthesis of colour pigments, overview
-
-
-
additional information
?
-
-
the enzyme is the key enzyme for delphinidin biosynthesis in the flavonoid biosynthetic pathway, biosynthesis of colour pigments, overview
-
-
-
additional information
?
-
Q6J210
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
Q6YLS3
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
Q84NG3
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
Q9FPN3
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
Nierembergia sp.
Q8LP20
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
Q304Q4
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
Q304Q4
substrate specificity of F3'H and the F3'5'H, flavonoid 3',5'-hydroxylase, EC 1.14.13.88, evolutionary derived from F3'H, is determined near the N-terminal end and the functional difference between these two enzymes near the C-terminal end, relatively few amino acids exchanges are required for the evolutionary extension of 3'- to 3',5'-hydroxylation activity, overview
-
-
-
additional information
?
-
Q304Q4
the enzyme is involved in biosynthesis of delphinidin-derived anthocyanins which are responsible for the rose to lilac flower colours of the petals, overview
-
-
-
additional information
?
-
Q304Q5
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
-
the enzyme catalyzes the 3',5'-hydroxylation of dihydroflavonols, the precursors of purple anthocyanins
-
-
-
additional information
?
-
P48418
key enzyme in the synthesis of 3',5'-hydroxylated anthocyanins, which are generally required for blue or purple flowers
-
-
-
additional information
?
-
-
key enzyme in the synthesis of 3',5'-hydroxylated anthocyanins, which are generally required for the expression of blue or purple flower color. Pigment composition analysis of transgenic plants suggests that the F3'5'H transgene not only creates or inhibits the biosynthetic pathway to 3',5'-hydroxylated anthocyanins but switches the pathway to 3',5'-hydroxylated or 3'-hydroxylated anthocyanins
-
-
-
additional information
?
-
-
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
P37120
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
-
enzyme is involved in anthocyanin biosynthesis. When expressed as a transgene in the red-skinned cultivar Desiree changes tuber skin color from red to purple
-
-
-
additional information
?
-
Q5EWY2
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
Q9FS35
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
-
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
-
-
-
additional information
?
-
Q3C210
the enzyme is involved in the biosynthetic pathway of delphinidin-based anthocyanins, as well as of the flavonols quercetin and myricetin and procyanidin and prodelphinidin, correlation of enzyme expression pattern and flavonoid composition, flavonoid composition in organs of Vitis vinifera, flavonoid biosynthetic pathways, overview
-
-
-
additional information
?
-
Q2PWV0
the enzyme plays a role in the phenyl-propanoid pathway and the biosynthesis of cyanidin- and delphinidin-based anthocyanin pigments in the socalled red cultivars of grapevine, metabolic profiling and colour variations, overview, the enzyme is responsible for flavonoid accumulation in tissues
-
-
-
additional information
?
-
Q2PWV1
the enzyme plays a role in the phenyl-propanoid pathway and the biosynthesis of cyanidin- and delphinidin-based anthocyanin pigments in the socalled red cultivars of grapevine, metabolic profiling and colour variations, overview, the enzyme is responsible for flavonoid accumulation in tissues
-
-
-
additional information
?
-
Q2PWV2
the enzyme plays a role in the phenyl-propanoid pathway and the biosynthesis of cyanidin- and delphinidin-based anthocyanin pigments in the socalled red cultivars of grapevine, metabolic profiling and colour variations, overview, the enzyme is responsible for flavonoid accumulation in tissues
-
-
-
additional information
?
-
Q2PWV3
the enzyme plays a role in the phenyl-propanoid pathway and the biosynthesis of cyanidin- and delphinidin-based anthocyanin pigments in the socalled red cultivars of grapevine, metabolic profiling and colour variations, overview, the enzyme is responsible for flavonoid accumulation in tissues
-
-
-
additional information
?
-
Q2PWV4
the enzyme plays a role in the phenyl-propanoid pathway and the biosynthesis of cyanidin- and delphinidin-based anthocyanin pigments in the socalled red cultivars of grapevine, metabolic profiling and colour variations, overview, the enzyme is responsible for flavonoid accumulation in tissues
-
-
-
additional information
?
-
Q2UYU7
transcriptional regulation of the enzyme in fruits, the enzyme is expressed after flowering, when proanthocyanidins are synthesized, accumulation of hydroxylated anthocyaniins in grape berries, flavonoid biosynthetic pathways, overview
-
-
-
additional information
?
-
-
flavonoid pathway during berry development, anthocyanin synthesis takes place mainly in postveraison, detailed overview, metabolite and expression profiling
-
-
-
additional information
?
-
-
the enzyme is a key enzyme in colour variation of the grape berry conforming to a peculiar pattern of genotype-specific expression of the whole set of anthocyanin genes in a direct transcript-metabolite phenotype relationship, the enzyme is involved in anthocyanin composition, colour intensity and colour hue of grapes at berry maturity, overview
-
-
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cytochrome b5
expression of cytchrome b5 in grape berries is correlated to enzyme expression during fruit development phases, overview
-
cytochrome P450
the enzyme is a member of the cytochrome P450 family
-
cytochrome P450
-
inhibition by a polyclonal antibody that inhibits higher plant NADPH-cytochrome p450 reductase is consistent with the suggestion that flavonoid 3',5'-hydroxylase is a monooxygenase consisting of cytochrome p450 and a NADPH-cytochrome P-450 reductase
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
RNAi
reduces transcript levels, thus affecting flower color, acylated delphinidins (dominating in the wild-type) including gentiodelphin are decreased to 12.0% while non-acylated delphinidins are increased to 66.0 and 69.7% (15.2% in wild-type) of total anthocyanins in two transformed strains (clone 1 lilac, clone 15 pale blue)
-
additional information
-
a polyclonal antibody that inhibits higher plant NADPH-cytochrome p450 reductase inhibits the flavonoid 3',5'-hydroxylase. No effect by diethylpyrocarbonate or phenylmethylsulfonyl fluoride
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries
-
additional information
transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries
-
additional information
transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries
-
additional information
transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries
-
additional information
transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries; transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 50fold higher in red berries versus green berries
-
additional information
-
drought stress leads to upregulation of the enzyme and of total anthocyanin biosynthesis in berries from dehydrated plants, the anthocyanin composition is enriched in more hydroxylated and more methoxylated derivatives, metabolite profiling, overview
-
additional information
-
water deficits increase total anthocyanin contents and highly upregulate the enzyme expression, overview
-
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
activities of recombinant chimeric mutant enzymes, overview
additional information
F3'5'H activity in ray floret enzyme extracts of 3 developmental stages, overview
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.5
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
F3'5'H activity in ray floret enzyme extracts of 3 developmental stages, overview
-
expressed in tuber skin only in presence of the anthocyanin regulatory locus I
additional information
immature; immature; immature; immature; immature
-
activity varies with the development of flowers, peaking immediately prior to and during anthesis, but is absent in mature flowers
wild-type fruit accumulates proanthocyanidin (condensed tannins) during development
berry skin and flesh; berry skin and flesh; berry skin and flesh; berry skin and flesh; berry skin and flesh
berry skin, transcriptional regulation of the enzyme, onset of expression after flowering, low expression at the onset of ripening, high expression after veraison concomitant with the accumulation of 3'- and 3',5'-hydroxylated anthocyanins, overview
berry skin of young and small, at the pre-veraison stage, and ripe fruits
-
quantitative expression analysis of the enzyme at different developmental stages in correlation to the anthocyanidin profile, overview
-
upregulation of expression during development in berry skin, accumulation of cyanidin-based anthocyanins and delphinidin-based anthocyanins
apex, apical leaflet, reddish pigmented shoot tips; apex, apical leaflet, reddish pigmented shoot tips; apex, apical leaflet, reddish pigmented shoot tips; apex, apical leaflet, reddish pigmented shoot tips; apex, apical leaflet, reddish pigmented shoot tips
-
low expression in developing grape leaf, low level of delphinidin-based anthocyanins, accumulation of cyanidin-based anthocyanins (consistent in green-yellow-, purple-, and black-colored skin cultivars)
additional information
CYP75A31 real-time PCR expression analysis in the vegetative tomato plant parts
additional information
-
CYP75A31 real-time PCR expression analysis in the vegetative tomato plant parts
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
activity declines when microsomal suspensions are subjected to freezing and thawing
-
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
75°C, storage in presence of 20% sucrose for periods of greater than 1 month results in significant loss of enzyme activity
-
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, genetic mapping, phylogenetic analysis, expression analysis and metabolic profiling, phenotypes; DNA and amino acid sequence determination and analysis, genetic mapping, phylogenetic analysis, expression analysis and metabolic profiling, phenotypes; DNA and amino acid sequence determination and analysis, genetic mapping, phylogenetic analysis, expression analysis and metabolic profiling, phenotypes; DNA and amino acid sequence determination and analysis, genetic mapping, phylogenetic analysis, expression analysis and metabolic profiling, phenotypes; DNA and amino acid sequence determination and analysis, genetic mapping, phylogenetic analysis, expression analysis and metabolic profiling, phenotypes
DNA and amino acid sequence determination and analysis, phylogenetic analysis 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, sequence comparison, genetic organization, and phylogenetic analysis
expression in Dendrathemum grandiflora transgenic plants using the Agrobacterium tumefaciens stran ABA 4404 transfection method
-
expression in Rosa hybrida transgenic plants, the mutant plants show the accumulation of a high percentage of delphinidin in selected cultuvars, while the wild-type lacks delphinidin and derivatives and the activity of F3'5'H
Viola sp.
-
expression of wild-type enzyme and chimeric mutants in yeast strain INVSc 1 microsomes
functional expression of the enzyme as fusion enzyme with a P450 reductase leading to biosynthesis of plant-specific di- and trihydroxylated flavonols in Escherichia coli strain BL21(DE3), feeding experiments and determination of the flavonoid spectra in different recombinant bacterial lines in vivo, overview
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gene CYP75A31, DNA and amino acid sequence determination and analysis, functional expression in Saccharomyces cerevisiae microsomes using vector pYeDP60, real-time PCR expression analysis
gene F3',5'h, DNA and amino acid sequence determination and analysis, genomic structure, expression pattern analysis
gene F3',5'H1, DNA and amino acid sequence determination and analysis, phylogenetic tree, developmental expression analysis, comparison of red and white cultivar enzyme expression levels, functional expression in Petunia hybrida altering the hosts' flower color and flavonoid composition
introduction of a flavonoid 3'5' hydroxylase sequence into Lotus root cultures. Expression of the transgene is associated with increased levels of condensed tannins, no alteration in polymer hydroxylation
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Met210 variant, DNA and amino acid sequence determination and analysis, semi-quantitative RT-PCR expression analysis; Val210 variant, DNA and amino acid sequence determination and analysis, semi-quantitative RT-PCR expression analysis
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PCR-amplification, transformation into Agrobacterium tumefaciens EHA101 by electroporation used to transform the blue-flowered Gentiana triflora x Gentiana scabra cultivar Albireo via leaf disc infection
subcloning of AK14, encoding flavonoid-3',5'-hydroxylase, into a plant expression vector and transforming it to pink tobacco (Nicotiana tabacum cv. Petit Havana SR1) and pink petunia (var. Falcon), both of which originally lack the enzyme
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subcloning of TG1, encoding flavonoid-3',5'-hydroxylase, into a plant expression vector and transforming it to pink tobacco (Nicotiana tabacum cv. Petit Havana SR1) which originally lacks the enzyme
when sense constructs are introduced into pink flower varieties that are deficient in the enzyme, transgenic plants show flower color changes from pink to magenta along with changes ihn anthocyanin composition. Some transgenic plants show novel pigmentation patterns, e.g. a star-shaped pattern. When sense constructs are introduced into blue flower petunia varieties, the flower color of the transgenic plants changes from deep blue to pale blue or even pale pink. Pigment composition analysis of transgenic plants suggests that the F3'5'H transgene not only creates or inhibits the biosynthetic pathway to 3',5'-hydroxylated anthocyanins but switches the pathway to 3',5'-hydroxylated or 3'-hydroxylated anthocyanins
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when VmFH1, encoding the flavonoid 3',5'-hydroxylase is expressed in transgenic petunia hybrida under the control of the cauliflower mosaic virus 35S promoter, some transgenic plants show drastic flower color alteration from red to deep red with deep purple sectors
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DNA and amino acid sequence determination and analysis, phylogenetic analysis 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, phylogenetic analysis 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, phylogenetic analysis 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, phylogenetic analysis 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, phylogenetic analysis 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, phylogenetic analysis 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, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, overview
Nierembergia sp.
DNA and amino acid sequence determination and analysis, phylogenetic analysis 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, phylogenetic analysis 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, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, overview
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DNA and amino acid sequence determination and analysis, phylogenetic analysis 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, phylogenetic analysis 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, phylogenetic analysis 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, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, overview
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DNA and amino acid sequence determination and analysis, sequence comparison, genetic organization, and phylogenetic analysis
DNA and amino acid sequence determination and analysis, sequence comparison, genetic organization, and phylogenetic analysis
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
berry skin accumulates cyanidin-based anthocyanins and delphinidin-based anthocyanins during development
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chimeric RNAi technology silences transcription of enzyme, in clone 15 (pale blue) more than in clone 1 (lilac)
expression of gene CYP75A31 increases in response to nitrogen deprivation, in accordance with other genes in the phenylpropanoid pathway, overview
in PCNA mutant, especially the relative expression compared to the substrate-competing flavonoid 3' hydroxylase sinks stronger with seasonal development than in the wild-type
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
F484Y/S487T
site-directed mutagenesis, altered substrate specificity compared to the wild-type enzyme
F48Y
site-directed mutagenesis, altered substrate specificity compared to the wild-type enzyme
S487A
site-directed mutagenesis, altered substrate specificity compared to the wild-type enzyme
S487Y
site-directed mutagenesis, altered substrate specificity compared to the wild-type enzyme
additional information
additional information
pollination-constant and non-astringent (PCNA) type mutants lose the ability to produce proanthocyanidin at an early stage in fruit development
additional information
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pollination-constant and non-astringent (PCNA) type mutants lose the ability to produce proanthocyanidin at an early stage in fruit development
additional information
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pink-flowered Gentiana scabra plants are bred from spontaneous mutations of Gentiana triflora blue-flowered gentian plants, two different transposable elements, terminal-repeat retrotransposon in miniature, inserted in flavonoid 3,5-hydroxylase gene contribute to pink flower coloration, overview
additional information
pink-flowered Gentiana scabra plants are bred from spontaneous mutations of Gentiana triflora blue-flowered gentian plants, two different transposable elements, terminal-repeat retrotransposon in miniature, inserted in flavonoid 3,5-hydroxylase gene contribute to pink flower coloration, overview
additional information
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pink-flowered Gentiana scabra plants are bred from spontaneous mutations of Gentiana triflora blue-flowered gentian plants, two different transposable elements, terminal-repeat retrotransposon in miniature, inserted in flavonoid 3,5-hydroxylase gene contribute to pink flower coloration, overview
additional information
introduction of a binary vector to silence flavonoid 3',5'-hydroxylase and anthocyanin 5,3'-aromatic acyltransferase via RNAi silencing downregulating gentiodelphin biosynthesis, thus affecting flower color
additional information
generation of chimeric constructs consisting of cDNA fragments of Osteospermum hybrida F3'5'H and Gerbera hybrida F3'H, EC 1.14.13.21, overview
additional information
redirection of anthocyanin synthesis in Osteospermum hybrida towards pelargonidin derivatives, which are not synthesized in wild-type plants, by expression of Gerbera hybrida dihydroflavonol 4-reductase, the mutant plants show altered flower colours due to synthesis of pelargonidin anthocyaninsssing Gerbera DFR with a construct or RNAi-mediated suppression of F3'5'H activity results in double transgenic plants accumulating predominantly pelargonidin derivatives in flowers, overview
additional information
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recombinant expression of the flavonoid 3',5'-hydroxylase from Petunia sp. in Dendrathemum grandiflora plants leads to competition of the endogenous flavonoid 3'-hydroxylase, EC 1.14.13.21, with the recombinant enzyme for the same substrates in the flavonoid biosynthetic pathway leading to a change in flower petal colors, phenotype, overview
additional information
Viola sp.
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establishment of a bluish color, achieved by delphinidin and derivatives, in Rosa hybrida by overexpression of the F3'5'H gene from Viola sp. and the dihydroflavonol 4-reductase gene from Iris hollandica, while the endogenous dihydroflavonol 4-reductase gene is downregulated, the ability for exclusive accumulation of delphinidin is inherited by the next generations, phenotype, overview
additional information
transgenic Petunia hybrida lines, overexpressing the enzyme from Vitis vinifera, produce high levels of the 3',4',5'-hydroxylated anthocyanin malvidin and very little 3',4'-hydroxylated anthocyanins, they also show a shift from kaempferol to quercetin when compared to the nontransgenic control, flower colours and phenotypes, white and red grape varieties exhibit different temporal expression of F3',5'H1 and cytochrome b5, overview
additional information
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transcriptional control of anthocyanin biosynthetic genes in extreme phenotypes for berry pigmentation of naturally occurring grapevines, overview
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
understanding the regulation of flavonoid hydroxylases could be used to modify flavonoid composition of fruits
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.88)
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