Information on EC 2.1.1.B76 - flavone/flavonol 7-O-methyltransferase

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The expected taxonomic range for this enzyme is: Populus

EC NUMBER
COMMENTARY hide
2.1.1.B76
preliminary BRENDA-supplied EC number
RECOMMENDED NAME
GeneOntology No.
flavone/flavonol 7-O-methyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + a flavone = S-adenosyl-L-homocysteine + a 7-methoxyflavone
show the reaction diagram
S-adenosyl-L-methionine + a flavonol = S-adenosyl-L-homocysteine + a 7-methoxyflavonol
show the reaction diagram
SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:flavone/flavonol 7-O-methyltransferase
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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rhamnetin inhibits the formation of beta-amyloid
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 + kaempferol
S-adenosyl-L-homocysteine + 3,7-O-dimethylkaempferol
show the reaction diagram
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activity only of enzyme mutant POMT7-M1, D257G, not of wild-type POMT7
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-
?
2 S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + 3,7-O-dimethylquercetin
show the reaction diagram
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activity only of enzyme mutant POMT7-M1, D257G, not of wild-type POMT7, molecular docking of quercetin into the modeled structure of Asp257Gly
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-
?
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone
S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
show the reaction diagram
S-adenosyl-L-methionine + 3',4',5,7-tetrahydroxyflavanone
S-adenosyl-L-homocysteine + 3,4',5-trihydroxy-7-methoxyflavanone
show the reaction diagram
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i.e. eriodictyol, 14% of the activity with apigenin (i.e. 5,7,4'-trihydroxyflavone)
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-
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S-adenosyl-L-methionine + 3,3',4',5,7-pentahydroxyflavone
S-adenosyl-L-homocysteine + 3,3',4',5-tetrahydroxy-7-methoxyflavone
show the reaction diagram
S-adenosyl-L-methionine + 3,4',5,7-tetrahydroxyflavanone
S-adenosyl-L-homocysteine + 3,4',5-trihydroxy-7-methoxyflavanone
show the reaction diagram
S-adenosyl-L-methionine + 3,5,7,4'-tetrahydroxy-3'-methoxyflavone
S-adenosyl-L-homocysteine + 3,5,4'-trihydroxy-7,3'-dimethoxyflavone
show the reaction diagram
S-adenosyl-L-methionine + 5,7,4'-trihydroxyflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyflavone
show the reaction diagram
S-adenosyl-L-methionine + kaempferol
S-adenosyl-L-homocysteine + 7-O-methylkaempferol
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + luteolin
S-adenosyl-L-homocysteine + 3,4',5-trihydroxy-7-methoxyflavanone
show the reaction diagram
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i.e. 5,7,3',4'-tetrahydroxyflavanone, 87% of the activity with apigenin (i.e. 5,7,4'-trihydroxyflavone)
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?
S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + 7-O-methylquercetin
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 + 3,3',4',5,7-pentahydroxyflavone
S-adenosyl-L-homocysteine + 3,3',4',5-tetrahydroxy-7-methoxyflavone
show the reaction diagram
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i.e. quercetin
i.e. rhamnetin
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?
S-adenosyl-L-methionine + kaempferol
S-adenosyl-L-homocysteine + 7-O-methylkaempferol
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + 7-O-methylquercetin
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
S-adenosyl-L-methionine
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0298 - 0.0324
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
0.0324 - 0.0378
3,4',5,7-tetrahydroxyflavanone
0.0298 - 0.0324
kaempferol
0.0324 - 0.0378
quercetin
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.064 - 0.071
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
0.064 - 0.07
3,4',5,7-tetrahydroxyflavanone
0.064 - 0.071
kaempferol
0.064 - 0.07
quercetin
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.9 - 2.4
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
19386
1.7 - 1.9
3,4',5,7-tetrahydroxyflavanone
11924
1.9 - 2.4
kaempferol
408
1.7 - 1.9
quercetin
137
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
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assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
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assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant GST-tagged wild-type POMT7 and mutant POMT7-M1 from Escherichia coli by glutathione affinity chromatography; recombinent POMT7 and mutants
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
; gene POMT7, error-prone polymerase chain reaction, expression of GST-tagged wild-type POMT7 and mutant POMT7-M1 in Escherichia coli
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expression in Escherichia coli as a glutathione S-transferase fusion protein
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functional POMT7 expression in Escherichia coli; gene POMT7, recombinant functional expression in Escherichia coli strain BL21(DE3), which is capable to transform quercetin into rhamnetin, coexpression with Escherichia coli SAM synthetase
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using Escherichia coli transformants harboring both PFNS-1 and POMT-7, naringenin could be converted into genkwanin
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D257G
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random mutagenesis, the mutant of POMT-7, POMT7-M1, has a novel regioselectivity, from large scale mutant screening, mutant D257G methylates the 3-hydroxyl group of flavonols in addition to 7-hydrdoxyl group
N257G
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the mutant methylates the 3-hydroxyl group of flavonols in addition to 7-hydrdoxyl group. The wild type POMT7 exhibits better activity toward kaempferol and quercetin than the mutant enzyme
additional information
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combines engineered and optimization of enzyme expression and activity with cofacor production in recombinant Escherichia coli for improved biosynthesis of rhamnetin; optimization of POMT7 expression and rhamnetin production in Escherichia coli, in addition, the S-adenosylmethionine biosynthesis pathway is engineered by coexpression of SAM synthetase, for optimal cofactor production, production of rhamnetin of up to 111 mg/l, overview
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pharmacology
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the enzyme reaction product rhmanetin, produced from quercetin, inhibits the formation of beta-amyloid. Rhamnetin holds great promise for use in therapeutic application in neurodegenerative disease, method evaluation, overview
synthesis