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Information on EC 2.1.1.128 - (RS)-norcoclaurine 6-O-methyltransferase for references in articles please use BRENDA:EC2.1.1.128Word Map on EC 2.1.1.128
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The enzyme appears in viruses and cellular organisms
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(RS)-norcoclaurine 6-O-methyltransferase
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S-adenosyl-L-methionine + (RS)-norcoclaurine = S-adenosyl-L-homocysteine + (RS)-coclaurine
S-adenosyl-L-methionine + (RS)-norcoclaurine = S-adenosyl-L-homocysteine + (RS)-coclaurine
bi-bi ping-pong mechanism
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S-adenosyl-L-methionine + (RS)-norcoclaurine = S-adenosyl-L-homocysteine + (RS)-coclaurine
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methyl group transfer
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methyl group transfer
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methyl group transfer
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(S)-reticuline biosynthesis I
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Isoquinoline alkaloid biosynthesis
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Biosynthesis of secondary metabolites
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S-adenosyl-L-methionine:(RS)-norcoclaurine 6-O-methyltransferase
The enzyme will also catalyse the 6-O-methylation of (RS)-norlaudanosoline to form 6-O-methyl-norlaudanosoline, but this alkaloid has not been found to occur in plants.
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(R,S)-norcoclaurine 6-O-methyltransferase
(S)-Coclaurine N-methyltransferase
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(S)-norcoclaurine 6-O-methyltransferase
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(S)-norcoclaurine-6-O-methyltransferase
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3’-hydroxy-N-methylcoclaurine 4’-O-methyltransferase
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Ec4’OMT shows clear 6-O-methylation activity for norcoclaurine and produced coclaurine
Methyltransferase, (S)-coclaurine N-
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Methyltransferase, norlaudanosoline
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Norcoclaurine 6-O-methyltransferase
S-Adenosyl-L-methionine:(S)-coclaurine-N-methyltransferase
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S-Adenosyl-L-methionine:norcoclaurine 6-O-methyltransferase
S-Adenosylmethionine:(R),(S)-norlaudanosoline-6-O-methyltransferase
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(R,S)-norcoclaurine 6-O-methyltransferase
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(R,S)-norcoclaurine 6-O-methyltransferase
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6-OMT
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6OMT
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Norcoclaurine 6-O-methyltransferase
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Norcoclaurine 6-O-methyltransferase
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Norcoclaurine 6-O-methyltransferase
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Norcoclaurine 6-O-methyltransferase
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S-Adenosyl-L-methionine:norcoclaurine 6-O-methyltransferase
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S-Adenosyl-L-methionine:norcoclaurine 6-O-methyltransferase
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Uniprot
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SwissProt
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cultivar BR086
SwissProt
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cv. Louisiana and Marianne
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opium poppy, cultivar Bea's Choice
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malfunction
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suppression of norcoclaurine 6-O-methyltransferase transcript levels significantly suppresses total alkaloid accumulation in opium poppy (73% compared to the controls). However, the relative abundance of morphine increased to 55% of the total alkaloid content. Suppression of the enzyme does not significantly affect (S)-3'-hydroxy-N-methylcoclaurine 1 or (S)-3'-hydroxy-N-methylcoclaurine 2 transcript levels
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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 + (R)-norlaudanosoline
S-Adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline + 7-O-methylnorlaudanosoline
S-Adenosyl-L-methionine + (R,S)-2,3-dihydroxy-9,10-dimethoxytetrahydroprotoberberine
S-Adenosyl-L-homocysteine + ?
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5% of the activity with (S)-norlaudanosoline
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S-Adenosyl-L-methionine + (R,S)-4'-O-methylnorlaudanosoline
S-Adenosyl-L-homocysteine + norprotosinomenine
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34% of the activity with (S)-norlaudanosoline
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S-Adenosyl-L-methionine + (R,S)-5'-O-methylnorlaudanosoline
S-Adenosyl-L-homocysteine + 6-O-methyllaudanosoline
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81% of the activity with (S)-norlaudanosoline
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S-adenosyl-L-methionine + (RS)-norcoclaurine
S-adenosyl-L-homocysteine + (RS)-coclaurine
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
S-adenosyl-L-methionine + (S)-norlaudanosoline
S-adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline
S-adenosyl-L-methionine + (S)-norlaudanosoline
S-adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline + 7-O-methylnorlaudanosoline
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + jatrorrhizine
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1% of the activity with (S)-norlaudanosoline
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S-Adenosyl-L-methionine + 2,3-dihydroxy-9,10-dimethoxyprotoberberine
S-Adenosyl-L-homocysteine + tetrahydrojatrorrhizine
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7% of the activity with (S)-norlaudanosoline
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S-adenosyl-L-methionine + laudanosoline
?
S-Adenosyl-L-methionine + laudanosoline
S-Adenosyl-L-homocysteine + tetrahydrocolumbamine
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79% of the activity with (S)-norlaudanosoline
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S-Adenosyl-L-methionine + norcoclaurine
S-Adenosyl-L-homocysteine + ?
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(S)-norcoclaurine and (R)-norcoclaurine
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S-Adenosyl-L-methionine + (R)-norlaudanosoline
S-Adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline + 7-O-methylnorlaudanosoline
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92% of the activity with (S)-norlaudanosoline
6-O-methylnorlaudanosoline + 7-O-methylnorlaudanosoline in the ratio 8:2
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S-Adenosyl-L-methionine + (R)-norlaudanosoline
S-Adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline + 7-O-methylnorlaudanosoline
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S-adenosyl-L-methionine + (RS)-norcoclaurine
S-adenosyl-L-homocysteine + (RS)-coclaurine
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?
S-adenosyl-L-methionine + (RS)-norcoclaurine
S-adenosyl-L-homocysteine + (RS)-coclaurine
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?
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
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?
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
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?
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
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ir
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
putative rate-limiting step enzymes in benzylisoquinoline alkaloid biosynthesis
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?
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
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?
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
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preferred substrate
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?
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
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putative rate-limiting step enzymes in benzylisoquinoline alkaloid biosynthesis
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S-adenosyl-L-methionine + (S)-norlaudanosoline
S-adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline
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S-adenosyl-L-methionine + (S)-norlaudanosoline
S-adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline
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putative rate-limiting step enzymes in benzylisoquinoline alkaloid biosynthesis
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S-adenosyl-L-methionine + (S)-norlaudanosoline
S-adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline
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S-adenosyl-L-methionine + (S)-norlaudanosoline
S-adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline + 7-O-methylnorlaudanosoline
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6-O-methylnorlaudanosoline + 7-O-methylnorlaudanosoline in the ratio 8:2
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S-adenosyl-L-methionine + (S)-norlaudanosoline
S-adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline + 7-O-methylnorlaudanosoline
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activity with (R,S)-norlaudanosoline is 76% of the activity with (S)-norcoclaurine
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S-adenosyl-L-methionine + laudanosoline
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low activity
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S-adenosyl-L-methionine + laudanosoline
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low activity
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?
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S-adenosyl-L-homocysteine + (S)-reticuline
S-adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
Q9LEL6
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S-adenosyl-L-methionine + (RS)-norcoclaurine
S-adenosyl-L-homocysteine + (RS)-coclaurine
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
S-adenosyl-L-methionine + (S)-norlaudanosoline
S-adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline
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putative rate-limiting step enzymes in benzylisoquinoline alkaloid biosynthesis
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S-adenosyl-L-methionine + (RS)-norcoclaurine
S-adenosyl-L-homocysteine + (RS)-coclaurine
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S-adenosyl-L-methionine + (RS)-norcoclaurine
S-adenosyl-L-homocysteine + (RS)-coclaurine
Q6WUC1
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S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
Q9LEL6
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S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
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S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
Q9LEL6
putative rate-limiting step enzymes in benzylisoquinoline alkaloid biosynthesis
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?
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
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putative rate-limiting step enzymes in benzylisoquinoline alkaloid biosynthesis
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additional information
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the enzyme requires divalent cations for activity
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5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizium
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10 mM, 50% inhibition
S-adenosyl-L-homocysteine
additional information
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not inhibited by chloromercuribenzenesulfonate and iodoacetamide
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Co2+
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Co2+
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5 mM, severe inhibition
Cu2+
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Cu2+
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5 mM, severe inhibition
Fe2+
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Fe2+
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5 mM, severe inhibition
Mn2+
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Mn2+
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5 mM, severe inhibition
Ni2+
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Ni2+
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5 mM, severe inhibition
S-adenosyl-L-homocysteine
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S-adenosyl-L-homocysteine
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Zn2+
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Zn2+
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5 mM, severe inhibition
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WRKY1
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CjWRKY1 is a necessary regulator to control overall gene expression in berberine biosynthesis
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1.1
(R,S)-4'-O-methylnorlaudanosoline
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0.3
(R,S)-laudanosoline
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0.2 - 2.23
(R,S)-norlaudanosoline
3.95
S-adenosyl-L-methionine
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0.05
S-adenosylmethionine
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with (S)-norlaudanosoline as cosubstrate
0.2
(R,S)-norlaudanosoline
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2.23
(R,S)-norlaudanosoline
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10
5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizium
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0.18
S-adenosyl-L-homocysteine
Coptis japonica;
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using (S)-norlaudanosoline as cosubstrate, in 0.3 M Tris-HCl (pH 7.5), 25mM sodium ascorbate, at 30°C
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additional information
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7.5
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7 - 9.5
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about 50% of maximal activity at pH 7.0 and 9.5
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25
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culture condition for Coptis japonica
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low enzyme level
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low enzyme level
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sieve elements of the phloem adjacent or proximal to laticifers
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constant enzyme level over 16 days of germination
brenda
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brenda
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brenda
additional information
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gene transcripts detected in all organs with highest levels in root and stem and lowest in leaf
brenda
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brenda
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brenda
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brenda
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immunogold labelling studies show the strict association with electron dense regions of the peripheral cytoplasm of sieve elements
brenda
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brenda
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Thalictrum flavum subsp. glaucum;
Q5C9L7
Thalictrum flavum subsp. glaucum;
Q5C9L7
Thalictrum flavum subsp. glaucum;
Q5C9L7
Thalictrum flavum subsp. glaucum;
Q5C9L7
Thalictrum flavum subsp. glaucum;
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38500
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x * 38500, immunoblotting
40000
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x * 40000, SDS-PAGE
40000
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x * 40000, SDS-PAGE, recombinant Ec4’OMT
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?
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x * 40000, SDS-PAGE
?
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x * 40000, SDS-PAGE, recombinant Ec4’OMT
?
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x * 38500, immunoblotting
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complete loss of activity after freezing in 30% glycerol solution
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4°C, 50% loss of activity after 4 weeks
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Q-Sepharose column chromatography and Bio-Gel HTP column chromatography
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recombinant protein using His-tag
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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 as His-tag fusion protein in Escherichia coli ER2566pLys S
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expressed in Escherichia coli
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expressed in Escherichia coli BL21(DE3) cells
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expressed in Eschscholzia californica; full-length cDNA of Coptis japonica 6OMT 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
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enzyme expression is upregulated in the high papaverine mutant pap1
the over-expression of regulatory factors AP2G, AN1-like, ERF2, GARP, MDB025 and WRKY1 increases the levels of codeinone reductase, (S-adenosyl-L-methionine:3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase) and (R,S)-norcoclaurine 6-O-methyltransferase transcripts by 10- to more than 100fold. The transcriptional activations translate into an enhancement of alkaloid production in opium poppy of up to at least 10fold
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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
synthesis
production of the economically important analgesic morphine and the antimicrobial agent berberine
synthesis
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production of the economically important analgesic morphine and the antimicrobial agent berberine
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6OMT_COPJA
347
38700
Swiss-Prot
6OMT_PAPSO
346
38511
Swiss-Prot
A0A0B4VG62_9MAGN
350
39221
TrEMBL
B9SUX9_RICCO
110
12590
TrEMBL
B9TKC4_RICCO
98
11209
TrEMBL
B9SUY0_RICCO
353
38999
TrEMBL
Q5C9L7_THLFG
350
39385
TrEMBL
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Rueffer, M.; Nagakura, N.; Zenk, M.H.
Partial purification and properties of S-adenosylmethionine:(R),(S)-norlaudanosoline-6-O-methyltransferase from Argemone platyceras cell culture
J. Med. Plant Res.
49
131-137
1983
Argemone platyceras, Papaver somniferum
brenda
Sato, F.; Tsujita, T.; Katagiri, Y.; Yoshida, S.; Yamada, Y.
Purification and characterization of S-adenosyl-L-methionine:norcoclaurine 6-O-methyltransferase from cultured Coptis japonica cells
Eur. J. Biochem.
225
125-131
1994
Coptis japonica
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
Coptis japonica, Coptis japonica (Q9LEL6), 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
Morishige, T.; Tamakoshi, M.; Takemura, T.; Sato, F.
Molecular characterization of O-methyltransferases involved in isoquinoline alkaloid biosynthesis in Coptis japonica
Proc. Jpn. Acad. Ser. B
86
757-768
2010
Coptis japonica
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, Papaver somniferum (Q6WUC1)
brenda
Galanie, S.; Smolke, C.
Optimization of yeast-based production of medicinal protoberberine alkaloids
Microb. Cell Fact.
14
144
2015
Papaver somniferum (Q6WUC1)
brenda
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