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Information on EC 1.14.20.6 - flavonol synthase and Organism(s) Arabidopsis thaliana and UniProt Accession Q96330

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IUBMB 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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Arabidopsis thaliana
UNIPROT: Q96330
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The taxonomic range for the selected organisms is: Arabidopsis thaliana
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
flavonol synthase, sbfls, mcfls, bnfls, ppfls, vcfls, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
flavonol synthase
-
flavonol synthase
PATHWAY SOURCE
PATHWAYS
-
-, -, -, -
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+.
CAS REGISTRY NUMBER
COMMENTARY hide
146359-76-4
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2S)-naringenin + 2-oxoglutarate + O2
dihydrokaempferol + kaempferol + succinate + CO2 + H2O
show the reaction diagram
poor substrate
-
-
?
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
show the reaction diagram
good substrate
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
show the reaction diagram
(2R)-naringenin + 2-oxoglutarate + O2
(2S,3R)-dihydrokaempferol + succinate + CO2 + H2O
show the reaction diagram
-
transhydroxylation
-
-
?
(2R)-naringenin + 2-oxoglutarate + O2
(2S,3S)-dihydrokaempferol + succinate + CO2 + H2O
show the reaction diagram
-
-
+ low amounts of kaempferol
-
?
(2R)-naringenin + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
-
-
-
-
?
(2R,3R)-trans-dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
show the reaction diagram
-
-
-
-
?
(2R,3S,4R)-trans-leucocyanidin + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
-
-
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3S)-cis-dihydrokaempferol + (2R,3R)-trans-dihydrokaempferol + apigenin + kaempferol + succinate + CO2 + H2O
show the reaction diagram
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3S)-dihydrokaempferol + (2S,3S)-dihydrokaempferol + kaempferol + succinate + CO2 + H2O
show the reaction diagram
-
-
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
-
-
-
-
?
dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
show the reaction diagram
-
-
-
-
?
dihydromyricetin + 2-oxoglutarate + O2
myricetin + succinate + CO2 + H2O
show the reaction diagram
-
-
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2 + H2O
show the reaction diagram
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
the enzyme is involved in the biosynthesis of flavonoids
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
the enzyme is involved in the biosynthesis of flavonoids
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Iron
coordinated by residues H220, D222, and H276
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.027 - 0.32
dihydroquercetin
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.015 - 0.056
dihydroquercetin
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
26.9
wild-type, 37°C
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
flower and floral bud, high expression level
Manually annotated by BRENDA team
of later vegetative stage
Manually annotated by BRENDA team
of young seedling
Manually annotated by BRENDA team
high expression level
Manually annotated by BRENDA team
additional information
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
the anthocyanin level of fls1-3 knock-out mutants is about two-fold higher than that of wild-type seedlings
physiological function
part of flavonoid biosynthesis pathway
malfunction
-
second functional flavonol synthase fls3 in case of fls1 mutant lines, lacking the active flavonol synthase
physiological function
part of flavonoid biosynthesis pathway
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
FLS1_ARATH
336
0
38282
Swiss-Prot
other Location (Reliability: 3)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
38000
x * 38000, SDS-PAGE, x * 64000, SDS-PAGE of fusion protein with glutathione S-transferase
64000
x * 38000, SDS-PAGE, x * 64000, SDS-PAGE of fusion protein with glutathione S-transferase
45000
-
about, SDS-PAGE and Western blot
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 38000, SDS-PAGE, x * 64000, SDS-PAGE of fusion protein with glutathione S-transferase
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
identification of putative residues for binding ferrous iron, i.e. H221, D223 and H277, binding 2-oxoglutarate, i.e. R287 and S289, and dihydroquercetin, i.e. H132, F134, K202, F293 and E295 via computational analyses
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D223E
no catalytic activity
E295L
7% of wild-type activity
E295Q
48% of wild-type activity
F134A
15% of wild-type activity
F134L
54% of wild-type activity
F293A
8% of wild-type activity
F293L
9% of wild-type activity
H132F
124% of wild-type activity
H132Y
83% of wild-type activity
H221W
no catalytic activity
H277F
no catalytic activity
K202M
24% of wild-type activity
K202R
12% of wild-type activity
R287K
no catalytic activity
S289T
48% of wild-type activity
additional information
-
wild-type, fls1-2 single mutant and ldox/fls1-2 double mutant, lacking acitve form of flavonol synthase and leucoanthocyanidin dioxygenase, EC 1.14.11.19
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli as glutathione S-transferase fusion protein
expression in Escherichia coli as thioredoxin fusion proteins
expressed in Escherichia coli strain BL21Star
-
expression in Escherichia coli
-
expression in Escherichia coli as thioredoxin fusion proteins
expression in Saccharomyces cereviseae strain INV Sc1 and in Escherichia coli BL21-A1
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
flavonol synthase FLS1 can be manipulated (i.e., silenced or overexpressed) to redirect the flavonoid biosynthetic pathway toward anthocyanin production without negative effects on plant growth and development
flavonol synthase FLS1 can be manipulated (i.e., silenced or overexpressed) to redirect the flavonoid biosynthetic pathway toward anthocyanin production without negative effects on plant growth and development. Overexpression of flavonol synthase FLS1 alters seed coat color (resulting in a light brown color), and also affects flavonoid accumulation. Flavonol synthase FLS1 overexpressing seedlings have lower levels of anthocyanin than those of the wild-type. Shoot tissues of flavonol synthase FLS1 overexpressiong plants exhibit lower flavonol levels than those of the wild-type
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Turnbull, J.J.; Nakajima, J.; Welford, R.W.; Yamazaki, M.; Saito, K.; Schofield, C.J.
Mechanistic studies on three 2-oxoglutarate-dependent oxygenases of flavonoid biosynthesis: anthocyanidin synthase, flavonol synthase, and flavanone 3beta-hydroxylase
J. Biol. Chem.
279
1206-1216
2004
Arabidopsis thaliana
Manually annotated by BRENDA team
Prescott, A.G.; Stamford, N.P.; Wheeler, G.; Firmin, J.L.
In vitro properties of a recombinant flavonol synthase from Arabidopsis thaliana
Phytochemistry
60
589-593
2002
Arabidopsis thaliana
Manually annotated by BRENDA team
Leonard, E.; Yan, Y.; Koffas, M.A.
Functional expression of a P450 flavonoid hydroxylase for the biosynthesis of plant-specific hydroxylated flavonols in Escherichia coli
Metab. Eng.
8
172-181
2006
Arabidopsis thaliana
Manually annotated by BRENDA team
Chua, C.S.; Biermann, D.; Goo, K.S.; Sim, T.S.
Elucidation of active site residues of Arabidopsis thaliana flavonol synthase provides a molecular platform for engineering flavonols
Phytochemistry
69
66-75
2008
Arabidopsis thaliana (Q96330), Arabidopsis thaliana
Manually annotated by BRENDA team
Owens, D.K.; Alerding, A.B.; Crosby, K.C.; Bandara, A.B.; Westwood, J.H.; Winkel, B.S.
Functional analysis of a predicted flavonol synthase gene family in Arabidopsis
Plant Physiol.
147
1046-1061
2008
Arabidopsis thaliana, Arabidopsis thaliana (Q96330)
Manually annotated by BRENDA team
Preuss, A.; Stracke, R.; Weisshaar, B.; Hillebrecht, A.; Matern, U.; Martens, S.
Arabidopsis thaliana expresses a second functional flavonol synthase
FEBS Lett.
583
1981-1986
2009
Arabidopsis thaliana
Manually annotated by BRENDA team
Stracke, R.; De Vos, R.C.; Bartelniewoehner, L.; Ishihara, H.; Sagasser, M.; Martens, S.; Weisshaar, B.
Metabolomic and genetic analyses of flavonol synthesis in Arabidopsis thaliana support the in vivo involvement of leucoanthocyanidin dioxygenase
Planta
229
427-445
2009
Arabidopsis thaliana (B1GV57), Arabidopsis thaliana (B2GVM7), Arabidopsis thaliana (B7SFQ0), Arabidopsis thaliana (Q96330), Arabidopsis thaliana (Q9FFQ5), Arabidopsis thaliana
Manually annotated by BRENDA team
Nguyen, N.H.; Kim, J.H.; Kwon, J.; Jeong, C.Y.; Lee, W.; Lee, D.; Hong, S.W.; Lee, H.
Characterization of Arabidopsis thaliana flavonol synthase 1 (FLS1)-overexpression plants in response to abiotic stress
Plant Physiol. Biochem.
103
133-142
2016
Arabidopsis thaliana (Q96330), Arabidopsis thaliana
Manually annotated by BRENDA team