2.1.1.76: quercetin 3-O-methyltransferase
This is an abbreviated version!
For detailed information about quercetin 3-O-methyltransferase, go to the full flat file.
Reaction
Synonyms
3-OMT, CdFOMT5, flavonoid 3-methyltransferase, flavonoid-O-methyltransferase, flavonol 3-O-methyltransferase, FOMT5, Mg2+-independent O-methyltransferase, MOMT3, More, quercetin 3-O-methyltransferase 1, S-adenosyl-L-methionine:quercetin 3-O-methyltransferase, trimethylfavonol 3'/5'-OMT
ECTree
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Substrates Products
Substrates Products on EC 2.1.1.76 - quercetin 3-O-methyltransferase
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REACTION DIAGRAM
4 S-adenosyl-L-methionine + quercetin
4 S-adenosyl-L-homocysteine + 3,3',5,7-tetramethoxyquercetin
whole-cell biocatalysis using CdFOMT5 expressed in Escherichia coli cells is performed using quercetin as a substrate, and 3,3',5,7-tetramethylated quercetin is obtained as the final product
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S-adenosyl-L-methionine + 3',5'-O-dimethylmyricetin
S-adenosyl-L-homocysteine + 3,3',5'-O-trimethylmyricetin
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18% activity compared to myricetin
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S-adenosyl-L-methionine + 3'-O-methylmyricetin
S-adenosyl-L-homocysteine + 3,3'-O-dimethylmyricetin
S-adenosyl-L-methionine + 3,5,7,3',4'-pentahydroxyflavone
S-adenosyl-L-homocysteine + 3-methoxy-5,7,3',4'-tetrahydroxyflavone
S-adenosyl-L-methionine + 3-O-methylquercetin
S-adenosyl-L-homocysteine + ?
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3% activity compared to myricetin
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S-adenosyl-L-methionine + 4'-O-methylkaempferol
S-adenosyl-L-homocysteine + 3,4'-O-dimethylkaempferol
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11% activity compared to myricetin
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S-adenosyl-L-methionine + 7-methylquercetin
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i.e. rhamnetin, 30% of the activity with quercetin
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S-adenosyl-L-methionine + 7-O-methylmyricetin
S-adenosyl-L-homocysteine + 3,7-O-dimethylquercetin
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104% activity compared to myricetin
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S-adenosyl-L-methionine + galangin
S-adenosyl-L-homocysteine + ?
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60% of the activity with quercetin
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S-adenosyl-L-methionine + isorhamnetin
S-adenosyl-L-homocysteine + ?
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88% of the activity with quercetin
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S-adenosyl-L-methionine + kaempferol
S-adenosyl-L-homocysteine + 3-O-methyl-kaempferol
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93% of the activity with quercetin
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S-adenosyl-L-methionine + kaempferol
S-adenosyl-L-homocysteine + 3-O-methylkaempferol
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53% activity compared to myricetin
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S-adenosyl-L-methionine + myricetin
S-adenosyl-L-homocysteine + 3-O-methyl-myricetin
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46% of the activity with quercetin
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S-adenosyl-L-methionine + myricetin
S-adenosyl-L-homocysteine + 3-O-methylmyricetin
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100% activity
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S-adenosyl-L-methionine + myricetin
S-adenosyl-L-homocysteine + ?
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S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + 3'-methoxyquercetin
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S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + 3-methoxyquercetin
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S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + 3-O-methyl-quercetin
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S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + 3-O-methylquercetin
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121% activity compared to myricetin
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S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + 5-methoxyquercetin
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S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + 7-methoxyquercetin
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S-adenosyl-L-methionine + tamarixetin
S-adenosyl-L-homocysteine + ?
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85% of the activity with quercetin
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S-adenosyl-L-homocysteine + 3,3'-O-dimethylmyricetin
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64% activity compared to myricetin
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S-adenosyl-L-methionine + 3'-O-methylmyricetin
S-adenosyl-L-homocysteine + 3,3'-O-dimethylmyricetin
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i.e. laricitrin, 43% activity compared to myricetin
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S-adenosyl-L-homocysteine + 3-methoxy-5,7,3',4'-tetrahydroxyflavone
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S-adenosyl-L-methionine + 3,5,7,3',4'-pentahydroxyflavone
S-adenosyl-L-homocysteine + 3-methoxy-5,7,3',4'-tetrahydroxyflavone
flavonol quercetin is the preferred substrate
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S-adenosyl-L-methionine + 3,5,7,3',4'-pentahydroxyflavone
S-adenosyl-L-homocysteine + 3-methoxy-5,7,3',4'-tetrahydroxyflavone
involved in lignin biosynthesis
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S-adenosyl-L-methionine + 3,5,7,3',4'-pentahydroxyflavone
S-adenosyl-L-homocysteine + 3-methoxy-5,7,3',4'-tetrahydroxyflavone
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S-adenosyl-L-methionine + 3,5,7,3',4'-pentahydroxyflavone
S-adenosyl-L-homocysteine + 3-methoxy-5,7,3',4'-tetrahydroxyflavone
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3-O-methylquercetin
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S-adenosyl-L-methionine + 3,5,7,3',4'-pentahydroxyflavone
S-adenosyl-L-homocysteine + 3-methoxy-5,7,3',4'-tetrahydroxyflavone
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enzymatic synthesis of polymethylated flavonol glucosides
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S-adenosyl-L-methionine + 3,5,7,3',4'-pentahydroxyflavone
S-adenosyl-L-homocysteine + 3-methoxy-5,7,3',4'-tetrahydroxyflavone
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involved in metabolism of secondary plant products, especially formation of lignin and detoxification of flavonoids
3-O-methylquercetin
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S-adenosyl-L-methionine + 3,5,7,3',4'-pentahydroxyflavone
S-adenosyl-L-homocysteine + 3-methoxy-5,7,3',4'-tetrahydroxyflavone
Citrofortunella microcarpa
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S-adenosyl-L-methionine + 3,5,7,3',4'-pentahydroxyflavone
S-adenosyl-L-homocysteine + 3-methoxy-5,7,3',4'-tetrahydroxyflavone
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the flavonoid-O-methyltransferase from Citrus depressa has a broad substrate specificity and regioselectivity. Isozyme CdFOMT5 exhibits O-methyltransferase activity for quercetin, naringenin, (-)-epicatechin, and equol using S-adenosyl-L-methionine (SAM) as a methyl donor. The recombinant CdFOMT5 CdFOMT5 can catalyze the O-methylation of at least three hydroxyl groups of quercetin, and di- or tri-O-methylated quercetin products are obtained by this enzymatic reaction. CdFMOT5 prefers flavonol (3-hydroxyflavone) to other flavonoid structures. Thus, substrate structure, especially the C-ring in flavonoids, may strongly affect the substrate preference, including regioselectivity, of CdFOMT5
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additional information
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the flavonoid-O-methyltransferase from Citrus depressa has a broad substrate specificity and regioselectivity. Isozyme CdFOMT5 exhibits O-methyltransferase activity for quercetin, naringenin, (-)-epicatechin, and equol using S-adenosyl-L-methionine (SAM) as a methyl donor. The recombinant CdFOMT5 CdFOMT5 can catalyze the O-methylation of at least three hydroxyl groups of quercetin, and di- or tri-O-methylated quercetin products are obtained by this enzymatic reaction. CdFMOT5 prefers flavonol (3-hydroxyflavone) to other flavonoid structures. Thus, substrate structure, especially the C-ring in flavonoids, may strongly affect the substrate preference, including regioselectivity, of CdFOMT5
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additional information
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the enzyme does not methylate 3',4',5'-O-trimethylmyricetin, 3,7,3',4'-O-methylquercetin, 3-methylquercetin, and 3,7,4'-O-trimethylkaempferol. The enzyme transfers a methyl group only to the 3-position hydroxyl
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