BRENDA - Enzyme Database show
show all sequences of 2.1.1.291

(R,S)-Reticuline 7-O-methyltransferase and (R,S)-norcoclaurine 6-O-methyltransferase of Papaver somniferum - cDNA cloning and characterization of methyl transfer enzymes of alkaloid biosynthesis in opium poppy

Ounaroon, A.; Decker, G.; Schmidt, J.; Lottspeich, F.; Kutchan, T.M.; Plant J. 36, 808-819 (2003)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
the recombinant protein is then expressed in Spodoptera frugiperda Sf9 cells in a baculovirus expression vector
Papaver somniferum
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.014
-
isovanillic acid
pH 8.0, 35C
Papaver somniferum
0.016
-
(S)-reticuline
pH 8.0, 35C
Papaver somniferum
0.017
-
guaiacol
pH 8.0, 35C
Papaver somniferum
0.017
-
(R)-reticuline
pH 8.0, 35C
Papaver somniferum
0.15
-
S-adenosyl-L-methionine
pH 8.0, 35C, cosubstrate isovanillic acid
Papaver somniferum
0.31
-
S-adenosyl-L-methionine
pH 8.0, 35C, cosubstrate guaiacol or (R)-reticuline
Papaver somniferum
0.36
-
S-adenosyl-L-methionine
pH 8.0, 35C, cosubstrate (S)-reticuline
Papaver somniferum
Molecular Weight [Da]
Molecular Weight [Da]
Molecular Weight Maximum [Da]
Commentary
Organism
39841
-
2 * 39841, calculated from sequence
Papaver somniferum
43000
-
2 * 43000, SDS-PAGE
Papaver somniferum
85000
-
gel filtration
Papaver somniferum
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
S-adenosyl-L-methionine + (R)-reticuline
Papaver somniferum
the enzyme is involved in tetrahydrobenzylisoquinoline biosynthesis
S-adenosyl-L-homocysteine + (R)-laudanine
-
-
?
S-adenosyl-L-methionine + (S)-reticuline
Papaver somniferum
the enzyme is involved in tetrahydrobenzylisoquinoline biosynthesis
S-adenosyl-L-homocysteine + (S)-laudanine
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Papaver somniferum
Q6WUC2
-
-
Purification (Commentary)
Commentary
Organism
-
Papaver somniferum
Reaction
Reaction
Commentary
Organism
S-adenosyl-L-methionine + (S)-reticuline = S-adenosyl-L-homocysteine + (S)-laudanine
(1)
Papaver somniferum
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
additional information
(R)-protosinomenine and (R,S)-isoorientaline are O-methylated at C-6. The ration of kcat/Km for C-7 O-methylation compared to C6-O-methylation is 3.8:1
723417
Papaver somniferum
?
-
-
-
-
S-adenosyl-L-methionine + (R)-reticuline
the enzyme is involved in tetrahydrobenzylisoquinoline biosynthesis
723417
Papaver somniferum
S-adenosyl-L-homocysteine + (R)-laudanine
-
-
-
?
S-adenosyl-L-methionine + (R)-reticuline
the enzyme methylates (S)- and (R)-reticuline with equal efficiency
723417
Papaver somniferum
S-adenosyl-L-homocysteine + (R)-laudanine
-
-
-
?
S-adenosyl-L-methionine + (R,S)-orientaline
-
723417
Papaver somniferum
?
-
-
-
?
S-adenosyl-L-methionine + (S)-reticuline
the enzyme is involved in tetrahydrobenzylisoquinoline biosynthesis
723417
Papaver somniferum
S-adenosyl-L-homocysteine + (S)-laudanine
-
-
-
?
S-adenosyl-L-methionine + (S)-reticuline
the enzyme methylates (S)- and (R)-reticuline with equal efficiency
723417
Papaver somniferum
S-adenosyl-L-homocysteine + (S)-laudanine
-
-
-
?
S-adenosyl-L-methionine + guaiacol
-
723417
Papaver somniferum
?
-
-
-
?
S-adenosyl-L-methionine + isovanillic acid
-
723417
Papaver somniferum
?
-
-
-
?
Subunits
Subunits
Commentary
Organism
dimer
2 * 39841, calculated from sequence; 2 * 43000, SDS-PAGE
Papaver somniferum
Temperature Optimum [C]
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
37
41
methylation of (R,S)-isoorientaline and isovanillic acid
Papaver somniferum
37
-
methylation of guaiacol, (R)-reticuline and (S)-reticuline
Papaver somniferum
39
-
methylation of (R)-protosinomenine
Papaver somniferum
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.02
-
isovanillic acid
pH 8.0, 35C
Papaver somniferum
0.07
-
(R)-reticuline
pH 8.0, 35C
Papaver somniferum
0.07
-
(S)-reticuline
pH 8.0, 35C
Papaver somniferum
0.1
-
guaiacol
pH 8.0, 35C
Papaver somniferum
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.5
9
methylation of (R,S)-isoorientaline
Papaver somniferum
7.5
-
isovanillic acid
Papaver somniferum
8
-
methylation of guaiacol, (R)-reticuline and (S)-reticuline
Papaver somniferum
9
-
methylation of (R)-protosinomenine
Papaver somniferum
Cloned(Commentary) (protein specific)
Commentary
Organism
the recombinant protein is then expressed in Spodoptera frugiperda Sf9 cells in a baculovirus expression vector
Papaver somniferum
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.014
-
isovanillic acid
pH 8.0, 35C
Papaver somniferum
0.016
-
(S)-reticuline
pH 8.0, 35C
Papaver somniferum
0.017
-
guaiacol
pH 8.0, 35C
Papaver somniferum
0.017
-
(R)-reticuline
pH 8.0, 35C
Papaver somniferum
0.15
-
S-adenosyl-L-methionine
pH 8.0, 35C, cosubstrate isovanillic acid
Papaver somniferum
0.31
-
S-adenosyl-L-methionine
pH 8.0, 35C, cosubstrate guaiacol or (R)-reticuline
Papaver somniferum
0.36
-
S-adenosyl-L-methionine
pH 8.0, 35C, cosubstrate (S)-reticuline
Papaver somniferum
Molecular Weight [Da] (protein specific)
Molecular Weight [Da]
Molecular Weight Maximum [Da]
Commentary
Organism
39841
-
2 * 39841, calculated from sequence
Papaver somniferum
43000
-
2 * 43000, SDS-PAGE
Papaver somniferum
85000
-
gel filtration
Papaver somniferum
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
S-adenosyl-L-methionine + (R)-reticuline
Papaver somniferum
the enzyme is involved in tetrahydrobenzylisoquinoline biosynthesis
S-adenosyl-L-homocysteine + (R)-laudanine
-
-
?
S-adenosyl-L-methionine + (S)-reticuline
Papaver somniferum
the enzyme is involved in tetrahydrobenzylisoquinoline biosynthesis
S-adenosyl-L-homocysteine + (S)-laudanine
-
-
?
Purification (Commentary) (protein specific)
Commentary
Organism
-
Papaver somniferum
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
additional information
(R)-protosinomenine and (R,S)-isoorientaline are O-methylated at C-6. The ration of kcat/Km for C-7 O-methylation compared to C6-O-methylation is 3.8:1
723417
Papaver somniferum
?
-
-
-
-
S-adenosyl-L-methionine + (R)-reticuline
the enzyme is involved in tetrahydrobenzylisoquinoline biosynthesis
723417
Papaver somniferum
S-adenosyl-L-homocysteine + (R)-laudanine
-
-
-
?
S-adenosyl-L-methionine + (R)-reticuline
the enzyme methylates (S)- and (R)-reticuline with equal efficiency
723417
Papaver somniferum
S-adenosyl-L-homocysteine + (R)-laudanine
-
-
-
?
S-adenosyl-L-methionine + (R,S)-orientaline
-
723417
Papaver somniferum
?
-
-
-
?
S-adenosyl-L-methionine + (S)-reticuline
the enzyme is involved in tetrahydrobenzylisoquinoline biosynthesis
723417
Papaver somniferum
S-adenosyl-L-homocysteine + (S)-laudanine
-
-
-
?
S-adenosyl-L-methionine + (S)-reticuline
the enzyme methylates (S)- and (R)-reticuline with equal efficiency
723417
Papaver somniferum
S-adenosyl-L-homocysteine + (S)-laudanine
-
-
-
?
S-adenosyl-L-methionine + guaiacol
-
723417
Papaver somniferum
?
-
-
-
?
S-adenosyl-L-methionine + isovanillic acid
-
723417
Papaver somniferum
?
-
-
-
?
Subunits (protein specific)
Subunits
Commentary
Organism
dimer
2 * 39841, calculated from sequence; 2 * 43000, SDS-PAGE
Papaver somniferum
Temperature Optimum [C] (protein specific)
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
37
41
methylation of (R,S)-isoorientaline and isovanillic acid
Papaver somniferum
37
-
methylation of guaiacol, (R)-reticuline and (S)-reticuline
Papaver somniferum
39
-
methylation of (R)-protosinomenine
Papaver somniferum
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.02
-
isovanillic acid
pH 8.0, 35C
Papaver somniferum
0.07
-
(R)-reticuline
pH 8.0, 35C
Papaver somniferum
0.07
-
(S)-reticuline
pH 8.0, 35C
Papaver somniferum
0.1
-
guaiacol
pH 8.0, 35C
Papaver somniferum
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.5
9
methylation of (R,S)-isoorientaline
Papaver somniferum
7.5
-
isovanillic acid
Papaver somniferum
8
-
methylation of guaiacol, (R)-reticuline and (S)-reticuline
Papaver somniferum
9
-
methylation of (R)-protosinomenine
Papaver somniferum
General Information
General Information
Commentary
Organism
physiological function
the enzyme is involved in in tetrahydrobenzylisoquinoline biosynthesis
Papaver somniferum
General Information (protein specific)
General Information
Commentary
Organism
physiological function
the enzyme is involved in in tetrahydrobenzylisoquinoline biosynthesis
Papaver somniferum
KCat/KM [mM/s]
kcat/KM Value [1/mMs-1]
kcat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
4.2
-
(R)-reticuline
pH 8.0, 35C
Papaver somniferum
4.5
-
(S)-reticuline
pH 8.0, 35C
Papaver somniferum
5.9
-
guaiacol
pH 8.0, 35C
Papaver somniferum
KCat/KM [mM/s] (protein specific)
KCat/KM Value [1/mMs-1]
KCat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
4.2
-
(R)-reticuline
pH 8.0, 35C
Papaver somniferum
4.5
-
(S)-reticuline
pH 8.0, 35C
Papaver somniferum
5.9
-
guaiacol
pH 8.0, 35C
Papaver somniferum
Other publictions for EC 2.1.1.291
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [C]
Temperature Range [C]
Temperature Stability [C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [C] (protein specific)
Temperature Range [C] (protein specific)
Temperature Stability [C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
657166
Weid
The roles of latex and the vas ...
Papaver somniferum
Proc. Natl. Acad. Sci. USA
101
13957-13962
2004
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3
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4
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723417
Ounaroon
(R,S)-Reticuline 7-O-methyltra ...
Papaver somniferum
Plant J.
36
808-819
2003
-
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1
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7
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3
2
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6
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1
1
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8
1
3
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4
4
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1
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7
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3
2
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1
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8
1
3
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4
4
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1
1
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3
3