Information on EC 2.1.1.116 - 3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.1.1.116
-
RECOMMENDED NAME
GeneOntology No.
3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine = S-adenosyl-L-homocysteine + (S)-reticuline
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
methyl group transfer
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
(S)-reticuline biosynthesis I
-
-
Isoquinoline alkaloid biosynthesis
-
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Metabolic pathways
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Biosynthesis of secondary metabolites
-
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase
Involved in isoquinoline alkaloid metabolism in plants. The enzyme has also been shown to catalyse the methylation of (RS)-laudanosoline, (S)-3'-hydroxycoclaurine and (RS)-7-O-methylnorlaudanosoline.
CAS REGISTRY NUMBER
COMMENTARY hide
132084-81-2
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Berberis koetineana
-
-
-
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
-
suppression of the gene encoding (S)-3'-hydroxy-N-methylcoclaurine 4-O-methyltransferase reduces papaverine content in opium poppy
metabolism
essential enzyme in the berberine biosynthetic pathway
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-homocysteine + (S)-reticuline
S-adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
show the reaction diagram
S-adenosyl-L-methionine + (R,S)-3'-hydroxy-N-methylcoclaurine
?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + (R,S)-6-O-methylnorlaudanosoline
?
show the reaction diagram
-
-
-
-
?
S-Adenosyl-L-methionine + (R,S)-7-O-methyllaudanosoline
S-Adenosyl-L-homocysteine + norprotosinomenine
show the reaction diagram
Berberis koetineana
-
93% of the activity relative to 3'-hydroxy-N-methyl-(S)-coclaurine
-
-
S-adenosyl-L-methionine + (R,S)-laudanosoline
?
show the reaction diagram
-
-
-
-
?
S-Adenosyl-L-methionine + (R,S)-laudanosoline
S-Adenosyl-L-homocysteine + 4'-O-methyllaudanosoline
show the reaction diagram
Berberis koetineana
-
84% of the activity relative to 3'-hydroxy-N-methyl-(S)-coclaurine
-
-
S-adenosyl-L-methionine + (R,S)-norlaudanosoline
?
show the reaction diagram
-
-
-
-
?
S-Adenosyl-L-methionine + (S)-3'-hydroxy-coclaurine
S-Adenosyl-L-homocysteine + (S)-norreticuline
show the reaction diagram
Berberis koetineana
-
10% of the activity relative to 3'-hydroxy-N-methyl-(S)-coclaurine
-
-
S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
?
show the reaction diagram
Berberis koetineana
-
the enzyme catalyzes the last step in (S)-reticuline biosynthesis
-
-
-
S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
show the reaction diagram
additional information
?
-
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-homocysteine + (S)-reticuline
S-adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
show the reaction diagram
S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
?
show the reaction diagram
Berberis koetineana
-
the enzyme catalyzes the last step in (S)-reticuline biosynthesis
-
-
-
S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
show the reaction diagram
additional information
?
-
-
the enzyme is central to the biosynthesis of tetrahydroisoquinoline-derived alkaloids
-
-
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(R)-3'-Hydroxy-coclaurine
Berberis koetineana
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-
(S)-3'-hydroxy-coclaurine
Berberis koetineana
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-
(S)-norreticuline
Berberis koetineana
-
-
(S)-reticuline
Berberis koetineana
-
-
3'-Hydroxy-N-methyl-(R)-coclaurine
Berberis koetineana
-
-
Berberine
Berberis koetineana
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-
Jatrorrhizine
Berberis koetineana
-
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
methyl jasmonate
salicylic acid
WRKY1
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CjWRKY1 is a necessary regulator to control overall gene expression in berberine biosynthesis
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yeast extract
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yeast extract induces a delayed accumulation of 4'OMT
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.081
(R,S)-3'-hydroxy-N-methylcoclaurine
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-
0.031
(R,S)-6-O-methylnorlaudanosoline
-
-
0.039
(R,S)-laudanosoline
-
-
0.037
(R,S)-norlaudanosoline
-
-
0.0045
3'-hydroxy-N-methyl-(S)-coclaurine
Berberis koetineana
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-
0.03 - 0.179
S-adenosyl-L-methionine
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
Berberis koetineana
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-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5
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culture condition for Eschscholzia californica
7
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with (R,S)-3'-hydroxy-N-methylcoclaurine as substrate
8.3 - 8.5
Berberis koetineana
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-
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 9
Berberis koetineana
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about 50% of maximal activity at pH 7 and at pH 9
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
24
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culture condition for Eschscholzia californica
25
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culture condition for Coptis japonica
35 - 40
Berberis koetineana
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40
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with (R,S)-3'-hydroxy-N-methylcoclaurine as substrate
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
Berberis koetineana
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Manually annotated by BRENDA team
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higher levels of 4'OMT mRNA in cultivar Marianne, compared with cultivar Louisiana
Manually annotated by BRENDA team
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lowest gene transcripts
Manually annotated by BRENDA team
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restricted to sieve elements adjacent or proximal to laticifers
Manually annotated by BRENDA team
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predominantly in parenchyma cells within the vascular bundle
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
39400
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immunoblot analysis
51000
Berberis koetineana
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gel filtration
75000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
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2 * 42500, SDS-PAGE, 2 * 39800, sequence analysis
monomer
Berberis koetineana
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1 * 40000, SDS-PAGE
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6
Berberis koetineana
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half-life: 15 days
20
Berberis koetineana
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half-life: 3 days
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 20% glycerol, stable for more than 1 year
Berberis koetineana
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
-
Berberis koetineana
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by Ni2+ affinity chromatography
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Eschscholtzia californica cells are frozen using liquid nitrogen and suspended in protein extraction buffer, the supernatant is collected after centrifugation, protein samples are fractionated by SDS-PAGE
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Eschscholtzia californica cells are frozen using liquid nitrogen and then homogenized, proteins are isolated in an extraction buffer and centrifuged, proteins are separated using SDS-PAGE
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on cobalt affinity column
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
full-length cDNA of Coptis japonica 4'OMT is cloned into the binary vector pBITXEl2 for introduction into Agrobacterium tumefaciens, for infection Eschscholzia californica seedlings are co-cultured with Agrobacterium tumefaciens; into the pET-21d vector for expression in Escherichia coli BL21DE3 cells
into pRSETB and introduced into Escherichia coli strain ER2566 pLys S
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into the pET-41a+ vector for expression in Escherichia coli BL21DE3 cells
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into vector pQE31 containing six histidines as an N-terminal tag and overexpressed in Escherichia coli SG13009
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isolation of molecular clone; isolation of molecular clone
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information