Information on EC 2.1.1.267 - flavonoid 3',5'-methyltransferase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
2.1.1.267
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RECOMMENDED NAME
GeneOntology No.
flavonoid 3',5'-methyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + a 3'-hydroxyflavonoid = S-adenosyl-L-homocysteine + a 3'-methoxyflavonoid
show the reaction diagram
(1)
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-
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S-adenosyl-L-methionine + a 5'-hydroxy-3'-methoxyflavonoid = S-adenosyl-L-homocysteine + a 3',5'-dimethoxyflavonoid
show the reaction diagram
(2)
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
methyl group transfer
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Flavone and flavonol biosynthesis
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phenylpropanoids methylation (ice plant)
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polymethylated myricetin biosynthesis (tomato)
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syringetin biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:flavonoid 3'-O-methyltransferase
Isolated from Vitis vinifera (grape) [2]. Most active with delphinidin 3-glucoside but also acts on cyanidin 3-glucoside, cyanidin, myricetin, quercetin and quercetin 3-glucoside. The enzyme from Catharanthus roseus was most active with myricetin [1].
CAS REGISTRY NUMBER
COMMENTARY hide
118251-36-8
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
the VvAOMT genes cluster results from gene duplication
malfunction
metabolism
CrOMT2 is involved in the biosynthesis of flavonol glycosides and anthocyanins in Catharanthus roeus
physiological function
additional information
ratio of methylated/non-methylated anthocyanins in berry skin of 32 unrelated cultivars, QTL mapping of anthocyanin methylation level, overview
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2 S-adenosyl-L-methionine + myricetin
2 S-adenosyl-L-homocysteine + syringetin
show the reaction diagram
eriodictyol + S-adenosyl-L-methionine
homoeriodictyol + S-adenosyl-L-homocysteine
show the reaction diagram
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11% of the activity with quercetin
-
-
?
laricitrin + S-adenosyl-L-methionine
syringetin + S-adenosyl-L-homocysteine
show the reaction diagram
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114% of the activity with quercetin
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-
?
luteolin + S-adenosyl-L-methionine
chrysoeriol + S-adenosyl-L-homocysteine
show the reaction diagram
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42% of the activity with quercetin
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-
?
quercetin + S-adenosyl-L-methionine
isorhamnetin + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 2,3-dihydromyricetin
S-adenosyl-L-homocysteine + 3'-O-methyl-2,3-dihydromyricetin
show the reaction diagram
-
-
-
?
S-adenosyl-L-methionine + 3'-O-methyl-2,3-dihydromyricetin
S-adenosyl-L-homocysteine + 3',5'-di-O-methyl-2,3-dihydromyricetin
show the reaction diagram
-
i.e. syringetin
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?
S-adenosyl-L-methionine + 3'-O-methyl-2,3-dihydroquercetin
S-adenosyl-L-homocysteine + 3',4'-di-O-methyl-2,3-dihydroquercetin
show the reaction diagram
-
-
-
?
S-adenosyl-L-methionine + 3'-O-methylmyricetin
S-adenosyl-L-homocysteine + 3',5'-di-O-methylmyricetin
show the reaction diagram
-
-
-
?
S-adenosyl-L-methionine + 3'-O-methylquercetin
S-adenosyl-L-homocysteine + 3',4'-di-O-methylquercetin
show the reaction diagram
-
-
-
?
S-adenosyl-L-methionine + 7,8-dihydroxyflavone
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
?
S-adenosyl-L-methionine + caffeoyl-coenzyme A
S-adenosyl-L-homocysteine + ?
show the reaction diagram
S-adenosyl-L-methionine + cyanidin 3-O-beta-D-glucoside
S-adenosyl-L-homocysteine + peonidin 3-O-beta-D-glucoside
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + cyanidin 3-O-beta-D-glucoside
S-adenosyl-L-homocysteine + peonidin 3-O-beta-D-glucoside + H+
show the reaction diagram
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-
-
?
S-adenosyl-L-methionine + delphinidin 3-O-beta-D-glucoside
S-adenosyl-L-homocysteine + petunidin 3-O-beta-D-glucoside
show the reaction diagram
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high activity
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-
?
S-adenosyl-L-methionine + delphinidin 3-O-glucoside
S-adenosyl-L-homocysteine + petunidin 3-O-beta-D-glucoside
show the reaction diagram
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-
-
?
S-adenosyl-L-methionine + dihydromyricetin
?
show the reaction diagram
two sequential methylations at the 3'- and 5'-positions of the B-ring in dihydromyricetin
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-
?
S-adenosyl-L-methionine + dihydromyricetin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
54% of the activity with myricetin
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?
S-adenosyl-L-methionine + dihydroquercetin
S-adenosyl-L-homocysteine + 3'-O-methyl-2,3-dihydroquercetin
show the reaction diagram
-
-
-
?
S-adenosyl-L-methionine + dihydroquercetin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
22% of the activity with myricetin
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?
S-adenosyl-L-methionine + fisetin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
analysis of binding constant and docking energy
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?
S-adenosyl-L-methionine + luteolin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
S-adenosyl-L-methionine + myricetin
?
show the reaction diagram
S-adenosyl-L-methionine + myricetin
S-adenosyl-L-homocysteine + 3'-O-methylmyricetin
show the reaction diagram
best substrate
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-
?
S-adenosyl-L-methionine + myricetin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
analysis of binding constant and docking energy
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?
S-adenosyl-L-methionine + myricetin
S-adenosyl-L-homocysteine + syringetin
show the reaction diagram
S-adenosyl-L-methionine + myricitin
S-adenosyl-L-homocysteine + laricitrin
show the reaction diagram
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two product isomers
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?
S-adenosyl-L-methionine + petunidin 3-O-beta-D-glucoside
S-adenosyl-L-homocysteine + malvidin 3-O-beta-D-glucoside
show the reaction diagram
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-
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?
S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + 3'-O-methylquercetin
show the reaction diagram
low activity
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-
?
S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + isorhamnetin
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + quercetin 3-O-beta-D-glucoside
S-adenosyl-L-homocysteine + isorhamnetin 3-O-beta-D-glucoside
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + quercetin 3-O-beta-D-rutinoside
S-adenosyl-L-homocysteine + isorhamnetin 3-O-beta-D-rutinoside
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + tricetin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
S-adenosyl-L-methionine + cyanidin 3-O-beta-D-glucoside
S-adenosyl-L-homocysteine + peonidin 3-O-beta-D-glucoside + H+
show the reaction diagram
G0YKW8
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-
-
?
S-adenosyl-L-methionine + delphinidin 3-O-glucoside
S-adenosyl-L-homocysteine + petunidin 3-O-beta-D-glucoside
show the reaction diagram
G0YKW8
-
-
-
?
S-adenosyl-L-methionine + myricetin
?
show the reaction diagram
Q8GSN1
involvement in biosynthesis of flavonol glycosides and anthocyanins
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S-adenosyl-L-methionine + petunidin 3-O-beta-D-glucoside
S-adenosyl-L-homocysteine + malvidin 3-O-beta-D-glucoside
show the reaction diagram
G0YKW8
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?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
S-adenosyl-L-methionine
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Co2+
isoform ROMT-15, may substitute for Mg2+; isoform ROMT-17, may substitute for Mg2+; the enzyme is metal-dependent, Mg2+ is the best cation for catalytic activity, Co2+ shows 41% of the activity with Mg2+ (with quercetin as substrate); the enzyme is metal-dependent, Mg2+ is the best cation for catalytic activity, Co2+ shows 82% of the activity with Mg2+ (with quercetin as substrate)
Mn2+
the enzyme is metal-dependent, Mg2+ is the best cation for catalytic activity, Mn2+ shows 69% of the activity with Mg2+ (with quercetin as substrate); the enzyme is metal-dependent, Mg2+ is the best cation for catalytic activity, Mn2+ shows 74% of the activity with Mg2+ (with quercetin as substrate)
Zn2+
isoform ROMT-15, poorly substitutes for Mg2+; isoform ROMT-17, poorly substitutes for Mg2+
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.072 - 0.076
caffeoyl-coenzyme A
0.012
delphinidin 3-O-beta-D-glucoside
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pH 7.0, 30C
0.0224
eriodictyol
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pH 7.5, 30C
0.00074 - 0.104
luteolin
0.044 - 0.08
myricetin
0.00057 - 0.1
quercetin
0.437
quercetin 3-O-beta-D-glucoside
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pH 7.0, 30C
0.036 - 0.072
tricetin
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.025
delphinidin 3-O-beta-D-glucoside
Solanum lycopersicum
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pH 7.0, 30C
0.055
eriodictyol
Solanum lycopersicum
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pH 7.5, 30C
0.03
luteolin
Solanum lycopersicum
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pH 7.5, 30C
0.02 - 0.026
quercetin
0.014
quercetin 3-O-beta-D-glucoside
Solanum lycopersicum
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pH 7.0, 30C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.08
delphinidin 3-O-beta-D-glucoside
Solanum lycopersicum
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pH 7.0, 30C
4983
2.45
eriodictyol
Solanum lycopersicum
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pH 7.5, 30C
2485
40.5
luteolin
Solanum lycopersicum
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pH 7.5, 30C
436
0.2 - 45.6
quercetin
137
0.032
quercetin 3-O-beta-D-glucoside
Solanum lycopersicum
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pH 7.0, 30C
5785
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 9
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loss of activity at pH 5.0-6.0, inactive below
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
assay at; assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
enzyme expression ratios in berry skins in populations A and B, MYB diplotype, overview
Manually annotated by BRENDA team
enzyme expression ratios in berry skins in populations A and B, MYB diplotype, overview
Manually annotated by BRENDA team
quantitative real-time PCR expression profiling of AOMT and AOMT2 in hairy roots, overview
Manually annotated by BRENDA team
; expressed in stems only; isoform ROMT-15, highest expression in root and stem
Manually annotated by BRENDA team
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
26300
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x * 26300, SDS-PAGE
27800
x * 27800, calculated, isoform ROMT-15
30600
x * 30600, SDS-PAGE, glutathione S-transferase fusion protein
31100
x * 31100, SDS-PAGE, glutathione S-transferase fusion protein
32000
x * 32000, calculated, isoform ROMT-17
39145
x * 39145, sequence calculation
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
; recombinant His-tagged OMT2 by nickel affinity chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
; gene CrOMT2, DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic tree, expression as His-tagged nezyme in Escherichia coli
expressed in Escherichia coli as glutathione S-transferase fusion protein; expressed in Escherichia coli as glutathione S-transferase fusion protein; isoform ROMT-15, expression in Escherichia coli; isoform ROMT-17, expression in Escherichia coli
expression in Escherichia coli
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gene FAOMT, expression analysis, MYB diplotypes at the color locus affect anthocyanin composition, relationship analysis between the genotypes of the markers closest to the major QTLs and the expression levels of anthocyanin biosynthetic genes
gene OMT, DNA and amino acid sequence determination and analysis, phylogenetic analysis, gene OMT shows patterns strongly correlating with both accumulation of anthocyanins and expression of anthocyanin biosynthesis genes, encoding dihydroflavonol reductase (DFR), flavonoid-3',5'-hydroxylase (F3'5'H), and anthocyanidin synthase (ANS)
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genes AOMT2, AOMT3, and AOMT1, DNA and amino acid sequence determination and analysis, expression analysis, association mapping with VvAOMT1 and VvAOMT2 and methylated anthocyanin profiles, overview
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D168L
isoform ROMT-15, complete loss of activity; mutation abolishes activity (with quercetin as substrate)
D194L
isoform ROMT-15, complete loss of activity; mutation abolishes activity (with quercetin as substrate)
D209L
isoform ROMT-17, complete loss of activity; mutation abolishes activity (with quercetin as substrate)
D234L
isoform ROMT-17, complete loss of activity; mutation abolishes activity (with quercetin as substrate)
E112L
isoform ROMT-17, 14% loss of activity; mutation results in 40% loss of activity (with quercetin as substrate)
E69L
isoform ROMT-15, 14% loss of activity; mutation results in 14% loss of activity (with quercetin as substrate)
N195I
isoform ROMT-15, complete loss of activity; mutation abolishes activity (with quercetin as substrate)
N235I
isoform ROMT-17, complete loss of activity; mutation abolishes activity (with quercetin as substrate)
additional information
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silencing of AnthOMT in hypocotyl tissue, several hypocotyls of three lines (57, 85 and 87) show an anthocyanin profile that is different to that of the wild-type, and show a strong reduction in malvidin-type anthocyanins, while other lines (64, 66 and 71) show only wild-type anthocyanin profiles