Information on EC 2.1.1.117 - (S)-scoulerine 9-O-methyltransferase

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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
2.1.1.117
-
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RECOMMENDED NAME
GeneOntology No.
(S)-scoulerine 9-O-methyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + (S)-scoulerine = S-adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
show the reaction diagram
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-
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-
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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
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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SYSTEMATIC NAME
IUBMB Comments
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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CAS REGISTRY NUMBER
COMMENTARY hide
164205-21-4
methyltransferase, (S)-scoularine 9- (Coptis japonica clone pCJSMT)
96380-65-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
var. subcauliata
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-
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
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the enzyme is involved in berberine biosynthesis
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SUBSTRATE
PRODUCT                       
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 + (R,S)-2,3,9,10-tetrahydroxytetrahydroprotoberberine
?
show the reaction diagram
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methylated at 50% of the rate of (S)-scoulerine
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-
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S-Adenosyl-L-methionine + (S)-3,9-dihydroxy-2,10-dimethoxytetrahydroprotoberberine
?
show the reaction diagram
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methylated at 4% of the rate of (S)-scoulerine
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S-Adenosyl-L-methionine + (S)-scoulerine
?
show the reaction diagram
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
show the reaction diagram
S-Adenosyl-L-methionine + 6-O-methylnorlaudanosoline
?
show the reaction diagram
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8% of the activity relative to (S)-scoulerine
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-
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S-Adenosyl-L-methionine + norlaudanosoline
?
show the reaction diagram
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2% of the activity relative to (S)-scoulerine
-
-
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S-Adenosyl-L-methionine + norreticuline
?
show the reaction diagram
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9% of the activity relative to (S)-scoulerine
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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 + (S)-scoulerine
?
show the reaction diagram
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
show the reaction diagram
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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
S-adenosylhomocysteine
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.042 - 0.17
S-adenosyl-L-methionine
0.1 - 1.6
scoulerine
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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-
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
9 - 9.5
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-
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5 - 10
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50% of maximal activity at pH 7.5 and at pH 10
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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low activity
Manually annotated by BRENDA team
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high activity; lateral; low activity; main root
Manually annotated by BRENDA team
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high activity
Manually annotated by BRENDA team
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 20% glycerol, 50% loss of activity after 7 days
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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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LINKS TO OTHER DATABASES (specific for EC-Number 2.1.1.117)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)