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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,
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(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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3'-hydroxy N-methylcoclaurine 4'-O-methyltransferase
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3'-hydroxy-(S)-N-methylcoclaurine-4'-O-methyltransferase
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3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase
3-hydroxy-N-methylcoclaurine 4-O-methyltransferase
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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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3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase
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3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase
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4'-OMT
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4'OMT
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S-adenosyl-L-methionine:3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase
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S-adenosyl-L-methionine:3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase
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S-adenosyl-L-homocysteine + (S)-reticuline
S-adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-adenosyl-L-methionine + (R,S)-3'-hydroxy-N-methylcoclaurine
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S-adenosyl-L-methionine + (R,S)-6-O-methylnorlaudanosoline
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S-Adenosyl-L-methionine + (R,S)-7-O-methyllaudanosoline
S-Adenosyl-L-homocysteine + norprotosinomenine
Berberis koetineana
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93% of the activity relative to 3'-hydroxy-N-methyl-(S)-coclaurine
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S-adenosyl-L-methionine + (R,S)-laudanosoline
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S-Adenosyl-L-methionine + (R,S)-laudanosoline
S-Adenosyl-L-homocysteine + 4'-O-methyllaudanosoline
Berberis koetineana
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84% of the activity relative to 3'-hydroxy-N-methyl-(S)-coclaurine
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S-adenosyl-L-methionine + (R,S)-norlaudanosoline
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S-Adenosyl-L-methionine + (S)-3'-hydroxy-coclaurine
S-Adenosyl-L-homocysteine + (S)-norreticuline
Berberis koetineana
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10% of the activity relative to 3'-hydroxy-N-methyl-(S)-coclaurine
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S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
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Berberis koetineana
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the enzyme catalyzes the last step in (S)-reticuline biosynthesis
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S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
additional information
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S-adenosyl-L-homocysteine + (S)-reticuline
S-adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
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S-adenosyl-L-homocysteine + (S)-reticuline
S-adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
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S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
Berberis koetineana
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S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
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S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
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S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
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S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
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S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
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additional information
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no activity with norcoclaurine, coclaurine, N-methylcoclaurine, reticuline, scoulerine, and tetrahydrocolumbamine
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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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additional information
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only tetrahydroxylated tetrahydrobenzylisoquinolines are accepted as substrates, methylation is tolerated only at the 6-hydroxy position, no methylation when catechol and guaiacol or the phenylpropanoids caffeic and ferulic acid are used as substrate
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S-adenosyl-L-homocysteine + (S)-reticuline
S-adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
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Berberis koetineana
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the enzyme catalyzes the last step in (S)-reticuline biosynthesis
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S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
additional information
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the enzyme is central to the biosynthesis of tetrahydroisoquinoline-derived alkaloids
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S-adenosyl-L-homocysteine + (S)-reticuline
S-adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
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S-adenosyl-L-homocysteine + (S)-reticuline
S-adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
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S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
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S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
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S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
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S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
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S-Adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
S-Adenosyl-L-homocysteine + (S)-reticuline
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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
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 pRSETB and introduced into Escherichia coli strain ER2566 pLys S
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into the pET-21d vector for expression in Escherichia coli BL21DE3 cells
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
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Frenzel, T.; Zenk, M.H.
S-Adenosyl-L-methionine: 3'-hydroxy-N-methyl-(S)-coclaurine-4'-O-methyl transferase, a regio- and stereoselective enzyme of the (S)-reticuline pathway
Phytochemistry
29
3505-3511
1990
Berberis koetineana
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brenda
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
brenda
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
brenda
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
brenda
Inui, T.; Tamura, K.; Fujii, N.; Morishige, T.; Sato, F.
Overexpression of Coptis japonica norcoclaurine 6-O-methyltransferase overcomes the rate-limiting step in Benzylisoquinoline alkaloid biosynthesis in cultured Eschscholzia californica
Plant Cell Physiol.
48
252-262
2007
Eschscholzia californica, Coptis japonica (Q9LEL5), Coptis japonica
brenda
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
brenda
Cho, H.; Lee-Parsons, C.W.; Yoon, S.H.; Rhee, H.S.; Park, J.M.
Enhanced benzophenanthridine alkaloid production and protein expression with combined elicitor in Eschscholtzia californica suspension cultures
Biotechnol. Lett.
29
2001-2005
2007
Eschscholzia californica
brenda
Cho, H.Y.; Son, S.Y.; Rhee, H.S.; Yoon, S.Y.; Lee-Parsons, C.W.; Park, J.M.
Synergistic effects of sequential treatment with methyl jasmonate, salicylic acid and yeast extract on benzophenanthridine alkaloid accumulation and protein expression in Eschscholtzia californica suspension cultures
J. Biotechnol.
135
117-122
2008
Eschscholzia californica
brenda
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
brenda
Kato, N.; Dubouzet, E.; Kokabu, Y.; Yoshida, S.; Taniguchi, Y.; Dubouzet, J.G.; Yazaki, K.; Sato, F.
Identification of a WRKY protein as a transcriptional regulator of benzylisoquinoline alkaloid biosynthesis in Coptis japonica
Plant Cell Physiol.
48
8-18
2007
Coptis japonica
brenda
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
brenda
Zhu, Q.; Zhu, M.; Fan, G.; Zou, J.; Feng, P.; Liu, Z.; Wang, W.
Molecular modeling and docking studies of 3-hydroxy-N-methylcoclaurine 4-O-methyltransferase from Coptis chinensis
Bull. Korean Chem. Soc.
35
62-68
2014
Coptis chinensis (B6RJT5)
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brenda
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
brenda
Galanie, S.; Smolke, C.
Optimization of yeast-based production of medicinal protoberberine alkaloids
Microb. Cell Fact.
14
144
2015
Papaver somniferum (Q7XB10)
brenda