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Information on EC 2.1.1.117 - (S)-scoulerine 9-O-methyltransferase for references in articles please use BRENDA:EC2.1.1.117Word Map on EC 2.1.1.117
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The enzyme appears in viruses and cellular organisms
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(S)-scoulerine 9-O-methyltransferase
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S-adenosyl-L-methionine + (S)-scoulerine = S-adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
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methyl group transfer
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berberine biosynthesis
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chelerythrine biosynthesis
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noscapine biosynthesis
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Isoquinoline alkaloid biosynthesis
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Biosynthesis of secondary metabolites
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S-adenosyl-L-methionine:(S)-scoulerine 9-O-methyltransferase
The product of this reaction is a precursor for protoberberine alkaloids in plants
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(S)-Adenosyl-L-methionine:(S)-scoularine 9-O-methyltransferase
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(S)-scoulerine 9-O-methyltransferase
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Methyltransferase, (S)-scoularine 9-
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Methyltransferase, (S)-scoularine 9- (Coptis japonica clone pCJSMT)
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scoulerine 9-O-methyltransferase
scoulerine-9-O-methyltransferase
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scoulerine 9-O-methyltransferase
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scoulerine 9-O-methyltransferase
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SMT
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164205-21-4
methyltransferase, (S)-scoularine 9- (Coptis japonica clone pCJSMT)
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brenda
var. subcauliata
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brenda
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UniProt
brenda
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brenda
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UniProt
brenda
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brenda
transient RNA silencing of scoulerine 9-O-methyltransferase expression by double stranded RNA in Coptis japonica protoplasts
Uniprot
brenda
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metabolism
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the enzyme is involved in berberine biosynthesis
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S-Adenosyl-L-methionine + (R,S)-2,3,9,10-tetrahydroxytetrahydroprotoberberine
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methylated at 50% of the rate of (S)-scoulerine
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S-Adenosyl-L-methionine + (S)-3,9-dihydroxy-2,10-dimethoxytetrahydroprotoberberine
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methylated at 4% of the rate of (S)-scoulerine
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S-Adenosyl-L-methionine + (S)-scoulerine
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S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
S-Adenosyl-L-methionine + 6-O-methylnorlaudanosoline
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8% of the activity relative to (S)-scoulerine
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S-Adenosyl-L-methionine + norlaudanosoline
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2% of the activity relative to (S)-scoulerine
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S-Adenosyl-L-methionine + norreticuline
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9% of the activity relative to (S)-scoulerine
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S-Adenosyl-L-methionine + (S)-scoulerine
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S-Adenosyl-L-methionine + (S)-scoulerine
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central role in orotoberberine biosynthesis
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S-Adenosyl-L-methionine + (S)-scoulerine
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the enzyme is responsible for a late step in the biosynthesis of berberine
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S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
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S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
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S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
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ir
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
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S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
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S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
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S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
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S-Adenosyl-L-methionine + (S)-scoulerine
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S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
S-Adenosyl-L-methionine + (S)-scoulerine
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S-Adenosyl-L-methionine + (S)-scoulerine
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central role in orotoberberine biosynthesis
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S-Adenosyl-L-methionine + (S)-scoulerine
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the enzyme is responsible for a late step in the biosynthesis of berberine
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S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
E0W6R9
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ir
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
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Berberine
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5 mM, 70% inhibition
Ca2+
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1 mM, 64% inhibition
Mn2+
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1 mM, 59% inhibition
palmatine
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5 mM, 70% inhibition
PCMB
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0.5 mM, 51% inhibition
Cu2+
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5 mM, 97% inhibition
Cu2+
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1 mM, 72% inhibition
S-adenosylhomocysteine
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S-adenosylhomocysteine
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0.042 - 0.17
S-adenosyl-L-methionine
0.042
S-adenosyl-L-methionine
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0.17
S-adenosyl-L-methionine
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0.1
scoulerine
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additional information
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7.5 - 10
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50% of maximal activity at pH 7.5 and at pH 10
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brenda
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low activity
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high activity; lateral; low activity; main root
brenda
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high activity
brenda
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activity of high berberine-producing cells is higher than that of non-selected cells
brenda
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brenda
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38364
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x * 38364, calculation from nucleotide sequence
41000
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x * 41000, SDS-PAGE
120000 - 140000
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gel filtration
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x * 41000, SDS-PAGE
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x * 38364, calculation from nucleotide sequence
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-20°C, 20% glycerol, 50% loss of activity after 7 days
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canadine-producing Saccharomyces cerevisiae strain harbors expression cassettes for seven heterologous enzymes: Papaper somniferum norcoclaurine 6-O-methyltransferase (Ps6OMT), Papaver somniferum 3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase 2 (Ps4'OMT), Papapver somniferum coclaurine N-methyltransferase (PsCNMT), Papaver somniferum berberine bridge enzyme (PsBBE), Thalictrum flavum scoulerine 9-O-methyltransferase (TfS9OMT), Thalictrum flavum canadine synthase (TfCAS), and Arabidopsis thaliana cytochrome P450 reductase 1 (CPR). The expression cassettes for the methyltransferases Ps6OMT, PsCNMT, and Ps4'OMT and the cytochrome P450 reductase CPR were chromosomally integrated, TfS9OMT and TfCAS are expressed from a high-copy plasmid, and PsBBE is expressed from a second high-copy plasmid
expressed in Eschscholzia californica cultivar Hitoezaki cells
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expression in Escherichia coli
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analysis
transient RNA silencing of scoulerine 9-O-methyltransferase expression by double stranded RNA in Coptis japonica protoplasts. Utility of gene silencing based on in vitro synthesized dsRNA to study function and behavior of endogenous enzymes
medicine
a Saccharomyces cerevisiae strain is engineered to express seven heterologous enzymes (Papaper somniferum norcoclaurine 6-O-methyltransferase (Ps6OMT), Papaver somniferum 3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase 2 (Ps4'OMT), Papapver somniferum coclaurine N-methyltransferase (PsCNMT), Papaver somniferum berberine bridge enzyme (PsBBE), Thalictrum flavum scoulerine 9-O-methyltransferase (TfS9OMT), Thalictrum flavum canadine synthase (TfCAS), and Arabidopsis thaliana cytochrome P450 reductase 1 (CPR)), resulting in protoberberine alkaloid production from a simple benzylisoquinoline alkaloid precursor. A number of strategies are implemented to improve flux through the pathway, including enzyme variant screening, genetic copy number variation, and culture optimization. This leads to an over 70-fold increase in canadine titer up to 1.8 mg/l. Increased canadine titers enable extension of the pathway to produce berberine, a major constituent of several traditional medicines in a microbial host. This strain is viable at pilot scale
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SMT_COPJA
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41665
Swiss-Prot
A0A2P6PAG7_ROSCH
364
40324
TrEMBL
A0A2P6Q5T8_ROSCH
361
40736
TrEMBL
A0A1P7ZIM6_ARGME
277
30390
TrEMBL
A0A2P6PEX7_ROSCH
365
40072
TrEMBL
A0A2P6QE06_ROSCH
169
18683
TrEMBL
Q5C9L2_THLFG
355
38591
TrEMBL
A0A2P6QGQ1_ROSCH
116
13527
TrEMBL
A0A2P6PA32_ROSCH
362
40180
TrEMBL
E0W6R9_9MAGN
350
38484
TrEMBL
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Fujiwara, H.; Takeshita, N.; Terano, Y.; Fitchen, J.H.; Tsujita, T.; Katagiri, Y.; Sato, F.; Yamada, Y.
Expression of (S)-scoulerine 9-O-methyltransferase in Coptis japonica plants
Phytochemistry
34
949-954
1993
Coptis japonica
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brenda
Sato, F.; Takeshita, N.; Fitchen, J.H.; Fujiwara, H.; Yamada, Y.
S-Adenosyl-L-methionine:scoulerine-9-O-methyltransferase from cultured Coptis japonica cells
Phytochemistry
32
659-664
1993
Coptis japonica
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brenda
Takeshita, N.; Fujiwara, H.; Mimura, H.; Fitchen, J.H.; Yamada, Y.; Sato, F.
Molecular cloning and characterization of S-adenosyl-L-methionine:scoulerine 9-O-methyltransferase from cultured cells of Coptis japonica
Plant Cell Physiol.
36
29-36
1995
Coptis japonica
brenda
Galneder, E.; Rueffer, M.; Wanner, G.; Tabata, M.; Zenk, M.H.
Alternative final steps in berberine biosynthesis in Coptis japonica cell cultures
Plant Cell Rep.
7
1-4
1988
Berberis stolonifera, Coptis japonica
brenda
Muemmler, S.; Rueffer, M.; Nagakura, N.; Zenk, M.H.
S-Adenosyl-L-methionine:(S)-scoulerine 9-O-methyltransferase, a highly stereo- and regio-specific enzyme in tetrahydroprotoberberine biosynthesis
Plant Cell Rep.
4
36-39
1985
Berberis wilsoniae
brenda
Dubouzet, J.G.; Morishige, T.; Fujii, N.; An, C.I.; Fukusaki, E.; Ifuku, K.; Sato, F.
Transient RNA silencing of scoulerine 9-O-methyltransferase expression by double stranded RNA in Coptis japonica protoplasts
Biosci. Biotechnol. Biochem.
69
63-70
2005
Coptis japonica, Coptis japonica (Q39522)
brenda
Takemura, T.; Ikezawa, N.; Iwasa, K.; Sato, F.
Metabolic diversification of benzylisoquinoline alkaloid biosynthesis through the introduction of a branch pathway in Eschscholzia californica
Plant Cell Physiol.
51
949-959
2010
Coptis japonica
brenda
Dang, T.T.; Facchini, P.J.
Cloning and characterization of canadine synthase involved in noscapine biosynthesis in opium poppy
FEBS Lett.
588
198-204
2014
Papaver somniferum
brenda
Zhu, Q.; Zhou, J.; Zhang, G.; Liao, H.
Homology modeling and molecular docking studies of (S)-scoulerine 9-O-methyltransferase from Coptis chinensis
Chin. J. Chem.
30
2533-2538
2012
Coptis chinensis (E0W6R9)
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brenda
Galanie, S.; Smolke, C.
Optimization of yeast-based production of medicinal protoberberine alkaloids
Microb. Cell Fact.
14
144
2015
Thalictrum flavum subsp. glaucum (Q5C9L2)
brenda
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