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Information on EC 1.14.20.6 - flavonol synthase
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EC Tree
1.14.20.6 flavonol synthaseIUBMB Comments
In addition to the desaturation of (2R,3R)-dihydroflavonols to flavonols, the enzyme from Citrus unshiu (satsuma mandarin) also has a non-specific activity that trans-hydroxylates the flavanones (2S)-naringenin and the unnatural (2R)-naringenin at C-3 to kaempferol and (2R,3R)-dihydrokaempferol, respectively . Requires Fe2+.
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Word Map
- 1.14.20.6
- flavonols
- flavanone
- chalcone
- dihydroflavonols
- kaempferol
- anthocyanidins
-
4-reductase
- dihydrokaempferol
-
3\'-hydroxylase
-
leucoanthocyanidin
-
r2r3-myb
- dihydroquercetin
-
3beta-hydroxylase
- fagopyrum
- tataricum
- 2-odds
- 2s-naringenin
- dihydroflavonol-4-reductase
- unshius
- analysis
- synthesis
-
tartary
-
flavonol-specific
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
flavonol synthase, sbfls, mcfls, bnfls, ppfls, vcfls, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
EC 1.14.11.23
-
-
formerly
-
flavonol synthase
FLS
FLS1
FLS2
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a dihydroflavonol + 2-oxoglutarate + O2 = a flavonol + succinate + CO2 + H2O
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
dihydroflavonol,2-oxoglutarate:oxygen oxidoreductase
In addition to the desaturation of (2R,3R)-dihydroflavonols to flavonols, the enzyme from Citrus unshiu (satsuma mandarin) also has a non-specific activity that trans-hydroxylates the flavanones (2S)-naringenin and the unnatural (2R)-naringenin at C-3 to kaempferol and (2R,3R)-dihydrokaempferol, respectively [2]. Requires Fe2+.
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CAS REGISTRY NUMBER
COMMENTARY
146359-76-4
-
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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
(+)-trans-dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
?
(2R)-naringenin + 2-oxoglutarate + O2
(-)-trans-dihydrokaempferol + succinate + CO2 + H2O
-
-
-
-
?
(2R)-naringenin + 2-oxoglutarate + O2
(2S,3R)-dihydrokaempferol + succinate + CO2 + H2O
-
transhydroxylation
-
-
?
(2R)-naringenin + 2-oxoglutarate + O2
(2S,3S)-dihydrokaempferol + succinate + CO2 + H2O
-
-
+ low amounts of kaempferol
-
?
(2R)-naringenin + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
-
-
-
-
?
(2R,3R)-trans-dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
-
?
(2R,3S,4R)-trans-leucocyanidin + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
-
-
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3S)-cis-dihydrokaempferol + (2R,3R)-trans-dihydrokaempferol + apigenin + kaempferol + succinate + CO2 + H2O
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3S)-dihydrokaempferol + (2S,3S)-dihydrokaempferol + kaempferol + succinate + CO2 + H2O
-
-
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
-
-
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
dihydrokaempferol + kaempferol + succinate + CO2 + H2O
poor substrate
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
?
3'-O-methyltaxifolin + 2-oxoglutarate + O2
isorhamnetin + succinate + CO2 + H2O
-
-
-
?
a dihydroflavonol + 2-oxoglutarate + O2
a flavonol + succinate + CO2 + H2O
-
-
-
?
cis-dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
weak reaction, only traces of kaempferol produced
-
-
?
pinobanksin + 2-oxoglutarate + O2
galangin + succinate + CO2 + H2O
-
-
-
?
trans-dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
?
(2R/3R)-dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
?
(2R/3R)-dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
?
(2R/3R)-dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
?
(2R/3R)-dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
?
(2R/3R)-dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
?
(2R/3R)-dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
?
(2R/3R)-dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
?
(2R/3R)-dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
?
(2R/3R)-dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
?
(2R/3R)-dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
-
?
(2R/3R)-dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3S)-cis-dihydrokaempferol + (2R,3R)-trans-dihydrokaempferol + apigenin + kaempferol + succinate + CO2 + H2O
-
-
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3S)-cis-dihydrokaempferol + (2R,3R)-trans-dihydrokaempferol + apigenin + kaempferol + succinate + CO2 + H2O
-
-
(2R,3S)-dihydrokaempferol is the predominant two-electron oxidation product
-
?
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
?
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
?
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
good substrate
-
-
?
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
?
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
?, r
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
r
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
?
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
?
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
ir
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
the mutated enzymes L311F, Y240P, F146I, A120M and L311F-A120M are all able to oxidize dihydrokaempferol to kaempferol, with respective catalytic activities relative to the wild type level of 355%, 104%, 86%, 162% and 175%. L311F substitution increases the flavonol synthase activity
-
-
?
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
ir
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
?
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
?
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
?
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
?
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
?
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
?
dihydromyricetin + 2-oxoglutarate + O2
myricetin + succinate + CO2 + H2O
-
-
-
?
dihydromyricetin + 2-oxoglutarate + O2
myricetin + succinate + CO2 + H2O
-
-
-
-
?
dihydromyricetin + 2-oxoglutarate + O2
myricetin + succinate + CO2 + H2O
-
-
-
?
dihydromyricetin + 2-oxoglutarate + O2
myricetin + succinate + CO2 + H2O
-
-
-
-
ir
dihydromyricetin + 2-oxoglutarate + O2
myricetin + succinate + CO2 + H2O
-
-
-
-
ir
dihydromyricetin + 2-oxoglutarate + O2
myricetin + succinate + CO2 + H2O
-
-
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
poor substrate
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
?, r
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
-
r
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
-
ir
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
-
ir
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
?
naringenin + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
?
naringenin + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
in a second reaction step with kaempferol 3-O-methyltransferase kaempferol is converted into 3-O-methylkaempferol
-
?
additional information
?
-
substrates are bound with similar affinity
-
-
?
additional information
?
-
-
the enzyme is involved in the biosynthesis of flavonoids
-
-
?
additional information
?
-
flavonol synthase and flavanone 3beta-hydroxylase are key enzymes in the biosynthesis of the UV-B protectant, kaempferol
-
-
?
additional information
?
-
-
flavonol synthase and flavanone 3beta-hydroxylase are key enzymes in the biosynthesis of the UV-B protectant, kaempferol
-
-
?
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NATURAL SUBSTRATE
NATURAL 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
a dihydroflavonol + 2-oxoglutarate + O2
a flavonol + succinate + CO2 + H2O
-
-
-
?
naringenin + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
?
(2R/3R)-dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
?
(2R/3R)-dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
?
(2R/3R)-dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
?
(2R/3R)-dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
-
?
(2R/3R)-dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
?
(2R/3R)-dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
?
(2R/3R)-dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
?
(2R/3R)-dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
?
(2R/3R)-dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
-
-
-
-
?
dihydromyricetin + 2-oxoglutarate + O2
myricetin + succinate + CO2 + H2O
-
-
-
?
dihydromyricetin + 2-oxoglutarate + O2
myricetin + succinate + CO2 + H2O
-
-
-
?
dihydromyricetin + 2-oxoglutarate + O2
myricetin + succinate + CO2 + H2O
-
-
-
-
?
additional information
?
-
-
the enzyme is involved in the biosynthesis of flavonoids
-
-
?
additional information
?
-
flavonol synthase and flavanone 3beta-hydroxylase are key enzymes in the biosynthesis of the UV-B protectant, kaempferol
-
-
?
additional information
?
-
-
flavonol synthase and flavanone 3beta-hydroxylase are key enzymes in the biosynthesis of the UV-B protectant, kaempferol
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
Iron
Fe2+
dependent on, the enzyme contains a ferrous iron (II) binding residue motif, i.e. the HxDxnH motif consisting of His217, Asp219, and His273
Fe2+
-
dependent on, the omission of Fe2+ in the reaction mixture results in 65% loss of enzyme activity
Iron
presence of Fe2+ in purification buffer is required to yield active enzyme
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
sodium 4,6-dioxo-2,2-dimethyl-5-(1-alloxyamino-butylidene)-cyclohexane-1-carboxylic acid methyl ester
3-hydroxy-5-oxo-4-butyryl-cyclohex-3-ene-1-carboxylic acid ethyl ester
-
1 mM 48% activity, 0.1 mM 88% activity
3-hydroxy-5-oxo-4-butyryl-cyclohex-3-ene-1-carboxylic acid ethyl ester
-
1 mM 48% activity, 0.1 mM 88% activity
3-hydroxy-5-oxo-4-cyclopropanecarbonyl-cyclohex-3-ene-1-carboxylic acid ethyl ester
-
1 mM 50% activity, 0.1 mM 77% activity
3-hydroxy-5-oxo-4-cyclopropanecarbonyl-cyclohex-3-ene-1-carboxylic acid ethyl ester
-
1 mM 50% activity, 0.1 mM 77% activity
3-hydroxy-5-oxo-4-propionyl-cyclohex-3-ene-1-(2-dimethylamino)-thiazole
-
1 mM 44% activity, 0.1 mM 73% activity
3-hydroxy-5-oxo-4-propionyl-cyclohex-3-ene-1-(2-dimethylamino)-thiazole
-
1 mM 44% activity, 0.1 mM 73% activity
3-hydroxy-5-oxo-4-propionyl-cyclohex-3-ene-1-carbaldehyde
-
1 mM 56% activity, 0.1 mM 82% activity
3-hydroxy-5-oxo-4-propionyl-cyclohex-3-ene-1-carbaldehyde
-
1 mM 56% activity, 0.1 mM 82% activity
3-hydroxy-5-oxo-4-propionyl-cyclohex-3-ene-1-carbothioic acid S-ethyl ester
-
1 mM 33% activity, 0.1 mM 90% activity
3-hydroxy-5-oxo-4-propionyl-cyclohex-3-ene-1-carbothioic acid S-ethyl ester
-
1 mM 33% activity, 0.1 mM 90% activity
3-hydroxy-5-oxo-4-propionyl-cyclohex-3-ene-1-pentanoic acid
-
1 mM 23% activity, 0.1 mM 64% activity
3-hydroxy-5-oxo-4-propionyl-cyclohex-3-ene-1-pentanoic acid
-
1 mM 23% activity, 0.1 mM 64% activity
calcium 3-hydroxy-5-oxo-4-propionyl-cyclohex-3-ene-1-carboxylate
-
1 mM 11% activity, 0.1 mM 29% relative activity
calcium 3-hydroxy-5-oxo-4-propionyl-cyclohex-3-ene-1-carboxylate
-
1 mM 11% activity, 0.1 mM 29% activity
pyridine-2,4-dicarboxylic acid diethyl ester
-
1 mM 3% activity, 0.1 mM 13% activity
pyridine-2,4-dicarboxylic acid diethyl ester
-
1 mM 3% activity, 0.1 mM 13% activity
sodium 4,6-dioxo-2,2-dimethyl-5-(1-alloxyamino-butylidene)-cyclohexane-1-carboxylic acid methyl ester
-
1 mM 78% activity, 0.1 mM 84% activity
sodium 4,6-dioxo-2,2-dimethyl-5-(1-alloxyamino-butylidene)-cyclohexane-1-carboxylic acid methyl ester
-
1 mM 78% activity, 0.1 mM 84% activity
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2-oxoglutarate
-
activity is completely abolished by the omission of 2-oxoglutarate from the reaction mixture
catalase
-
without the addition of catalase, the enzyme activity is decreased to approximately 45%
-
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Infections
Modulation of Arabidopsis Flavonol Biosynthesis Genes by Cyst and Root-Knot Nematodes.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.024
(2R/3R)-dihydrokaempferol
-
in 10 mM Tris/HCl buffer (pH 8.0), at 37°C
0.031
(2R/3R)-dihydroquercetin
-
in 10 mM Tris/HCl buffer (pH 8.0), at 37°C
0.001
dihydrokaempferol
-
in 0.1 M K2HPO4/KH2PO4 (0.6 M sorbitol, 0.4% Na-ascorbate, pH 7.25) with 0.095 nmol dihydrokaempferol, 50 nmol 2-oxoglutarate and 10 nmol FeSO4 hydrate at 30°C
0.001
dihydrokaempferol
-
in 0.1 M K2HPO4/KH2PO4 (0.6 M sorbitol, 0.4% Na-ascorbate, pH 7.25), 50 nmol 2-oxoglutarate and 10 nmol FeSO4 hydrate at 30°C
0.0584
dihydrokaempferol
-
recombinant FLS1, pH not specified in the publication, temperature not specified in the publication
0.0012
dihydroquercetin
-
in 0.1 M K2HPO4/KH2PO4 (0.6 M sorbitol, 0.4% Na-ascorbate, pH 7.25) with 0.095 nmol dihydrokaempferol, 50 nmol 2-oxoglutarate and 10 nmol FeSO4 hydrate at 30°C
0.0012
dihydroquercetin
-
in 0.1 M K2HPO4/KH2PO4 (0.6 M sorbitol, 0.4% Na-ascorbate, pH 7.25) with 0.095 nmol dihydrokaempferol, 50 nmol 2-oxoglutarate and 10 nmol FeSO4 hydrate at 30°C
0.1511
dihydroquercetin
-
recombinant FLS1, pH not specified in the publication, temperature not specified in the publication