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Information on EC 2.1.1.116 - 3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase and Organism(s) Papaver somniferum and UniProt Accession Q7XB11

for references in articles please use BRENDA:EC2.1.1.116
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EC Tree
IUBMB Comments
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.
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This record set is specific for:
Papaver somniferum
UNIPROT: Q7XB11
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Word Map
The taxonomic range for the selected organisms is: Papaver somniferum
The enzyme appears in selected viruses and cellular organisms
Synonyms
4'omt, 4'-omt, 3'-hydroxy-n-methylcoclaurine 4'-o-methyltransferase, (s)-3'-hydroxy-n-methylcoclaurine-4'-o-methyltransferase, 3'-hydroxy-(s)-n-methylcoclaurine-4'-o-methyltransferase, ps4'omt, s-adenosyl-l-methionine:3'-hydroxy-n-methylcoclaurine 4'-o-methyltransferase, (r,s)-3'-hydroxy-n-methylcoclaurine 4'-o-methyltransferase, s-adenosyl-l-methionine:(r,s)-3'-hydroxy-n-methylcoclaurine 4'-o-methyltransferase, (s)-3'-hydroxy-n-methylcoclaurine 4-o-methyltransferase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
(R,S)-3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase
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(S)-3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase
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(S)-3'-hydroxy-N-methylcoclaurine 4-O-methyltransferase
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(S)-3'-hydroxy-N-methylcoclaurine-4'-O-methyltransferase
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4'-OMT
4'OMT
Methyltransferase, (S)-3'-hydroxy-N-methylcoclaurine 4'-
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S-Adenosyl-L-methionine: 3'-hydroxy-N-methyl-(S)-coclaurine-4'-O-methyl transferase
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S-adenosyl-L-methionine:(R,S)-3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase
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S-adenosyl-L-methionine:3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase
SAM:3'-hydroxy-N-methyl-(S)-coclaurine-4'-O-methyltransferase
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
methyl group transfer
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
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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)-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)-laudanosoline
?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + (R,S)-norlaudanosoline
?
show the reaction diagram
-
-
-
-
?
S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL 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 + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
show the reaction diagram
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-
-
-
?
additional information
?
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the enzyme is central to the biosynthesis of tetrahydroisoquinoline-derived alkaloids
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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
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-
0.039
(R,S)-laudanosoline
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-
0.037
(R,S)-norlaudanosoline
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-
0.136 - 0.179
S-adenosyl-L-methionine
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
-
with (R,S)-3'-hydroxy-N-methylcoclaurine as substrate
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40
-
with (R,S)-3'-hydroxy-N-methylcoclaurine as substrate
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Ps4'OMT1
SwissProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
4'OMT mRNA level is comparatively low
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
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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suppression of the gene encoding (S)-3'-hydroxy-N-methylcoclaurine 4-O-methyltransferase reduces papaverine content in opium poppy
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
4OMT1_PAPSO
354
0
39402
Swiss-Prot
other Location (Reliability: 1)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
39400
-
immunoblot analysis
39800
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2 * 42500, SDS-PAGE, 2 * 39800, sequence analysis
42500
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2 * 42500, SDS-PAGE, 2 * 39800, sequence analysis
75000
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gel filtration
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
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2 * 42500, SDS-PAGE, 2 * 39800, sequence analysis
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
by Ni2+ affinity chromatography
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on cobalt affinity column
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
isolation of molecular clone
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
into pRSETB and introduced into Escherichia coli strain ER2566 pLys S
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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
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
additional information
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Weid, M.; Ziegler, J.; Kutchan, T.M.
The roles of latex and the vascular bundle in morphine biosynthesis in the opium poppy, Papaver somniferum
Proc. Natl. Acad. Sci. USA
101
13957-13962
2004
Papaver somniferum
Manually annotated by BRENDA team
Facchini, P.J.; Park, S.U.
Developmental and inducible accumulation of gene transcripts involved in alkaloid biosynthesis in opium poppy
Phytochemistry
64
177-186
2003
Papaver somniferum (Q7XB10), Papaver somniferum (Q7XB11), Papaver somniferum
Manually annotated by BRENDA team
Samanani, N.; Alcantara, J.; Bourgault, R.; Zulak, K.G.; Facchini, P.J.
The role of phloem sieve elements and laticifers in the biosynthesis and accumulation of alkaloids in opium poppy
Plant J.
47
547-563
2006
Papaver somniferum
Manually annotated by BRENDA team
Ziegler, J.; Diaz-Chavez, M.L.; Kramell, R.; Ammer, C.; Kutchan, T.M.
Comparative macroarray analysis of morphine containing Papaver somniferum and eight morphine free Papaver species identifies an O-methyltransferase involved in benzylisoquinoline biosynthesis
Planta
222
458-471
2005
Papaver somniferum
Manually annotated by BRENDA team
Apuya, N.R.; Park, J.H.; Zhang, L.; Ahyow, M.; Davidow, P.; Van Fleet, J.; Rarang, J.C.; Hippley, M.; Johnson, T.W.; Yoo, H.D.; Trieu, A.; Krueger, S.; Wu, C.Y.; Lu, Y.P.; Flavell, R.B.; Bobzin, S.C.
Enhancement of alkaloid production in opium and California poppy by transactivation using heterologous regulatory factors
Plant Biotechnol. J.
6
160-175
2008
Papaver somniferum
Manually annotated by BRENDA team
Desgagne-Penix, I.; Facchini, P.
Systematic silencing of benzylisoquinoline alkaloid biosynthetic genes reveals the major route to papaverine in opium poppy
Plant J.
72
331-344
2012
Papaver somniferum
Manually annotated by BRENDA team
Pathak, S.; Lakhwani, D.; Gupta, P.; Mishra, B.; Shukla, S.; Asif, M.; Trivedi, P.
Comparative transcriptome analysis using high papaverine mutant of Papaver somniferum reveals pathway and uncharacterized steps of papaverine biosynthesis
PLoS ONE
8
e65622
2013
Papaver somniferum
Manually annotated by BRENDA team
Galanie, S.; Smolke, C.
Optimization of yeast-based production of medicinal protoberberine alkaloids
Microb. Cell Fact.
14
144
2015
Papaver somniferum (Q7XB10)
Manually annotated by BRENDA team