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EC Tree
IUBMB Comments 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.
The enzyme appears in viruses and cellular organisms
Synonyms
6-omt, norcoclaurine 6-o-methyltransferase, (s)-norcoclaurine-6-o-methyltransferase, s-adenosyl-l-methionine:norcoclaurine 6-o-methyltransferase, (s)-coclaurine n-methyltransferase, (s)-norcoclaurine 6-o-methyltransferase, (r,s)-norcoclaurine 6-o-methyltransferase, ps6omt,
more
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(R,S)-norcoclaurine 6-O-methyltransferase
(S)-Coclaurine N-methyltransferase
-
-
-
-
(S)-norcoclaurine 6-O-methyltransferase
-
-
(S)-norcoclaurine-6-O-methyltransferase
-
3-hydroxy-N-methylcoclaurine 4-O-methyltransferase
-
Ec4OMT shows clear 6-O-methylation activity for norcoclaurine and produced coclaurine
Methyltransferase, (S)-coclaurine N-
-
-
-
-
Methyltransferase, norlaudanosoline
-
-
-
-
Norcoclaurine 6-O-methyltransferase
S-Adenosyl-L-methionine:(S)-coclaurine-N-methyltransferase
-
-
-
-
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
-
-
(R,S)-norcoclaurine 6-O-methyltransferase
-
-
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
-
-
Norcoclaurine 6-O-methyltransferase
-
-
S-Adenosyl-L-methionine:norcoclaurine 6-O-methyltransferase
-
-
-
-
S-Adenosyl-L-methionine: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-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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S-adenosyl-L-homocysteine + (S)-reticuline
S-adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
-
-
-
?
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 + ?
-
5% of the activity with (S)-norlaudanosoline
-
-
?
S-Adenosyl-L-methionine + (R,S)-4'-O-methylnorlaudanosoline
S-Adenosyl-L-homocysteine + norprotosinomenine
-
34% of the activity with (S)-norlaudanosoline
-
?
S-Adenosyl-L-methionine + (R,S)-5'-O-methylnorlaudanosoline
S-Adenosyl-L-homocysteine + 6-O-methyllaudanosoline
-
81% of the activity with (S)-norlaudanosoline
-
?
S-adenosyl-L-methionine + (R,S)-norlaudanosoline
S-adenosyl-L-homocysteine + (RS)-6-O-methylnorlaudanosoline
-
-
-
-
?
S-adenosyl-L-methionine + (R,S)-norlaudanosoline
S-adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline + 7-O-methylnorlaudanosoline
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
-
1% of the activity with (S)-norlaudanosoline
-
?
S-Adenosyl-L-methionine + 2,3-dihydroxy-9,10-dimethoxyprotoberberine
S-Adenosyl-L-homocysteine + tetrahydrojatrorrhizine
-
7% of the activity with (S)-norlaudanosoline
-
?
S-adenosyl-L-methionine + laudanosoline
?
S-Adenosyl-L-methionine + laudanosoline
S-Adenosyl-L-homocysteine + tetrahydrocolumbamine
-
79% of the activity with (S)-norlaudanosoline
-
?
S-Adenosyl-L-methionine + norcoclaurine
S-Adenosyl-L-homocysteine + ?
-
(S)-norcoclaurine and (R)-norcoclaurine
-
-
?
S-Adenosyl-L-methionine + (R)-norlaudanosoline
S-Adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline + 7-O-methylnorlaudanosoline
-
92% of the activity with (S)-norlaudanosoline
6-O-methylnorlaudanosoline + 7-O-methylnorlaudanosoline in the ratio 8:2
?
S-Adenosyl-L-methionine + (R)-norlaudanosoline
S-Adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline + 7-O-methylnorlaudanosoline
-
-
-
-
?
S-adenosyl-L-methionine + (R,S)-norlaudanosoline
S-adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline + 7-O-methylnorlaudanosoline
-
-
-
-
?
S-adenosyl-L-methionine + (R,S)-norlaudanosoline
S-adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline + 7-O-methylnorlaudanosoline
-
-
-
-
?
S-adenosyl-L-methionine + (RS)-norcoclaurine
S-adenosyl-L-homocysteine + (RS)-coclaurine
-
-
-
-
?
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)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
-
-
-
-
?
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
-
-
-
-
ir
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
-
-
-
?
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
putative rate-limiting step enzymes in benzylisoquinoline alkaloid biosynthesis
-
-
?
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
-
-
-
?
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
-
-
-
-
?
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
-
preferred substrate
-
-
?
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
-
putative rate-limiting step enzymes in benzylisoquinoline alkaloid biosynthesis
-
-
?
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
-
-
-
-
?
S-adenosyl-L-methionine + (S)-norlaudanosoline
S-adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline + 7-O-methylnorlaudanosoline
-
-
6-O-methylnorlaudanosoline + 7-O-methylnorlaudanosoline in the ratio 8:2
?
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
?
low activity
-
-
?
S-adenosyl-L-methionine + laudanosoline
?
-
low activity
-
-
?
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S-adenosyl-L-homocysteine + (S)-reticuline
S-adenosyl-L-methionine + 3'-hydroxy-N-methyl-(S)-coclaurine
-
-
-
?
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
-
-
?
S-adenosyl-L-methionine + (RS)-norcoclaurine
S-adenosyl-L-homocysteine + (RS)-coclaurine
-
-
-
-
?
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)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
-
-
-
?
S-adenosyl-L-methionine + (S)-norcoclaurine
S-adenosyl-L-homocysteine + (S)-coclaurine
putative rate-limiting step enzymes in benzylisoquinoline alkaloid biosynthesis
-
-
?
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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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
sanguinarine
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slow tight-binding inhibitor
Co2+
-
-
Co2+
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5 mM, severe inhibition
Cu2+
-
-
Cu2+
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5 mM, severe inhibition
Fe2+
-
-
Fe2+
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5 mM, severe inhibition
Mn2+
-
-
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
-
-
Zn2+
-
-
Zn2+
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5 mM, severe inhibition
additional information
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not inhibited by chloromercuribenzenesulfonate and iodoacetamide
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additional information
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not inhibitory: berberine up to 1 mM
-
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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
-
-
0.3
(R,S)-laudanosoline
-
-
0.015 - 2.23
(R,S)-norlaudanosoline
3.95
S-adenosyl-L-methionine
-
-
0.05
S-adenosylmethionine
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with (S)-norlaudanosoline as cosubstrate
0.015
(R,S)-norlaudanosoline
-
pH 8.0, 30°C
0.2
(R,S)-norlaudanosoline
-
-
2.23
(R,S)-norlaudanosoline
-
-
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0.15
(R,S)-norlaudanosoline
-
pH 8.0, 30°C
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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
-
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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-
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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
-
culture condition for Coptis japonica
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brenda
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UniProt
brenda
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brenda
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brenda
isoform 6OMT1
UniProt
brenda
isoform 6OMT2
UniProt
brenda
-
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-
brenda
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Uniprot
brenda
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brenda
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-
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brenda
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SwissProt
brenda
cultivar BR086
SwissProt
brenda
cv. Louisiana and Marianne
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brenda
opium poppy, cultivar Bea's Choice
-
-
brenda
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low enzyme level
brenda
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low enzyme level
brenda
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sieve elements of the phloem adjacent or proximal to laticifers
brenda
-
-
brenda
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constant enzyme level over 16 days of germination
brenda
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brenda
-
-
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
-
-
brenda
-
-
brenda
-
-
brenda
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-
immunogold labelling studies show the strict association with electron dense regions of the peripheral cytoplasm of sieve elements
brenda
-
-
-
brenda
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malfunction
-
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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6OMT_COPJA
347
0
38700
Swiss-Prot
Secretory Pathway (Reliability: 3 )
6OMT_PAPSO
346
0
38511
Swiss-Prot
other Location (Reliability: 3 )
6OMT_THLFG
350
0
39385
Swiss-Prot
other Location (Reliability: 5 )
A0A0B4VGY7_PODPE
373
0
41941
TrEMBL
other Location (Reliability: 1 )
B9SUY0_RICCO
353
0
38999
TrEMBL
other Location (Reliability: 1 )
A0A0B4VG62_SINHE
350
0
39221
TrEMBL
Secretory Pathway (Reliability: 4 )
B9TKC4_RICCO
98
0
11209
TrEMBL
other Location (Reliability: 2 )
B9TM05_RICCO
98
0
11062
TrEMBL
other Location (Reliability: 2 )
B9SUX9_RICCO
110
0
12590
TrEMBL
Secretory Pathway (Reliability: 5 )
A0A2Z5FRS1_9MAGN
355
0
39476
TrEMBL
-
A0A2Z5FRS5_9MAGN
346
0
38597
TrEMBL
-
A0A2Z5FRT2_9MAGN
350
0
38497
TrEMBL
Mitochondrion (Reliability: 3 )
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38500
-
x * 38500, immunoblotting
85000
-
gel filtration, recombinant protein
40000
-
x * 40000, SDS-PAGE
40000
-
x * 40000, SDS-PAGE, recombinant Ec4OMT
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?
-
x * 40000, SDS-PAGE
?
-
x * 40000, SDS-PAGE, recombinant Ec4OMT
?
-
x * 38500, immunoblotting
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structures of apo-6OMT, the binary complex 6OMT/SAH and the two ternary complexes 6OMT/SAH/norlaudanosoline and 6OMT/SAH/sanguinarine, refined to a resolution of 2.6, 1.9, 1.6 and 1.8 A, respectively
-
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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
-
expressed in Escherichia coli
-
expressed in Escherichia coli BL21(DE3) cells
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expressed in Eschscholzia californica
expression in Escherichia coli
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
expression in Escherichia coli
-
expression in Escherichia coli
expression in Escherichia coli
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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
production of the economically important analgesic morphine and the antimicrobial agent berberine
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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
Eschscholzia californica, Coptis japonica (Q9LEL6), Coptis japonica
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
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