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EC Tree
The expected taxonomic range for this enzyme is: Carapichea ipecacuanha
Synonyms
CiOMT1, IpeOMT1,
more
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IpeOMT1
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S-adenosyl-L-methionine + cephaeline = S-adenosyl-L-homocysteine + emetine
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S-adenosyl-L-methionine:cephaeline 6'-O-methyltransferase
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S-adenosyl-L-methionine + (R)-norprotosinomenine
S-adenosyl-L-homocysteine + ?
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?
S-adenosyl-L-methionine + (R,S)-isococlaurine
S-adenosyl-L-homocysteine + ?
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?
S-adenosyl-L-methionine + (R,S)-isoorientaline
S-adenosyl-L-homocysteine + ?
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?
S-adenosyl-L-methionine + (R,S)-norcoclaurine
S-adenosyl-L-homocysteine + ?
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?
S-adenosyl-L-methionine + (R,S)-protosinomenine
S-adenosyl-L-homocysteine + ?
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?
S-adenosyl-L-methionine + (S)-4'-O-methyllaudanosoline
S-adenosyl-L-homocysteine + ?
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?
S-adenosyl-L-methionine + (S)-norprotosinomenine
S-adenosyl-L-homocysteine + ?
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?
S-adenosyl-L-methionine + 1alpha-(S)-N-deacetylisoipecoside
S-adenosyl-L-homocysteine + 6-O-methyl-N-deacetylisoipecoside
S-adenosyl-L-methionine + 7-O-methyl-N-deacetylisoipecoside
S-adenosyl-L-homocysteine + 6,7-O,O-dimethyl-N-deacetylisoipecoside
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?
S-adenosyl-L-methionine + cephaeline
S-adenosyl-L-homocysteine + emetine
S-adenosyl-L-methionine + N-deacetylisoipecoside
S-adenosyl-L-homocysteine + 6-O-methyl-N-deacetylipecoside
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?
additional information
?
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S-adenosyl-L-methionine + 1alpha-(S)-N-deacetylisoipecoside
S-adenosyl-L-homocysteine + 6-O-methyl-N-deacetylisoipecoside
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?
S-adenosyl-L-methionine + 1alpha-(S)-N-deacetylisoipecoside
S-adenosyl-L-homocysteine + 6-O-methyl-N-deacetylisoipecoside
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the iminium cation, one of the spontaneous reaction products of 6-O-methyl-N-deacetylisoipecoside aglycon, might be an intermediate of emetine biosynthesis
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?
S-adenosyl-L-methionine + cephaeline
S-adenosyl-L-homocysteine + emetine
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?
S-adenosyl-L-methionine + cephaeline
S-adenosyl-L-homocysteine + emetine
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?
S-adenosyl-L-methionine + cephaeline
S-adenosyl-L-homocysteine + emetine
the enzyme is involved in emetine biosynthesis. It does not catalyze the 7'-O-methylation of 7'-O-demethylcephaeline, the preceding step in the biosynthesis of emetine
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?
S-adenosyl-L-methionine + cephaeline
S-adenosyl-L-homocysteine + emetine
6'-O-methylation
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?
additional information
?
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IpeOMT1 does not catalyze the 7'-O-methylation of 7'-O-demethylcephaeline. IpeOMT1 shows broad substrate specificity towards the intermediates in emetine biosynthesis. IpeOMT1 dominantly catalyzes 6-O-methylation of the 6,7-dihydroxy- and 6-hydroxy-7-methoxyisoquinolines. The regional substrate specificity at the last step of emetine biosynthesis is restricted to 6'-O-methylation
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?
additional information
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the enzyme is also active on 7'-O-demethylcephaeline forming cephaeline, overview
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?
additional information
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substrate specificity of CiOMT2, overview
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additional information
?
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IpeOMT1 does not catalyze the 7'-O-methylation of 7'-O-demethylcephaeline. IpeOMT1 shows broad substrate specificity towards the intermediates in emetine biosynthesis. IpeOMT1 dominantly catalyzes 6-O-methylation of the 6,7-dihydroxy- and 6-hydroxy-7-methoxyisoquinolines. The regional substrate specificity at the last step of emetine biosynthesis is restricted to 6'-O-methylation
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?
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S-adenosyl-L-methionine + 1alpha-(S)-N-deacetylisoipecoside
S-adenosyl-L-homocysteine + 6-O-methyl-N-deacetylisoipecoside
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the iminium cation, one of the spontaneous reaction products of 6-O-methyl-N-deacetylisoipecoside aglycon, might be an intermediate of emetine biosynthesis
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?
S-adenosyl-L-methionine + cephaeline
S-adenosyl-L-homocysteine + emetine
additional information
?
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the enzyme is also active on 7'-O-demethylcephaeline forming cephaeline, overview
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?
S-adenosyl-L-methionine + cephaeline
S-adenosyl-L-homocysteine + emetine
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?
S-adenosyl-L-methionine + cephaeline
S-adenosyl-L-homocysteine + emetine
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?
S-adenosyl-L-methionine + cephaeline
S-adenosyl-L-homocysteine + emetine
the enzyme is involved in emetine biosynthesis. It does not catalyze the 7'-O-methylation of 7'-O-demethylcephaeline, the preceding step in the biosynthesis of emetine
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?
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S-adenosyl-L-methionine
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S-adenosyl-L-methionine
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additional information
no effect by EDTA, Ca2+, and Mg2+
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Co2+
53% inhibition at 5 mM
Mn2+
31% inhibition at 5 mM
Ni2+
83% inhibition at 5 mM
Zn2+
90% inhibition at 5 mM
additional information
poor inhibition by iodoacetamide
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0.105
7-O-methyl-N-deacetylisoipecoside
pH 7.5, 30ưC
0.107
N-deacetylisoipecoside
pH 7.5, 30ưC
0.042
S-adenosyl-L-homocysteine
pH 7.5, 30ưC, cosubstrate: N-deacetylisoipecoside
0.097
S-adenosyl-L-methionine
pH 6.8, 30ưC, recombinant CiOMT1
0.068
cephaeline
pH 6.8, 30ưC, recombinant CiOMT1
0.08
cephaeline
pH 7.5, 30ưC
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0.0204
7-O-methyl-N-deacetylisoipecoside
pH 7.5, 30ưC
0.00028
cephaeline
pH 7.5, 30ưC
0.0113
N-deacetylisoipecoside
pH 7.5, 30ưC
0.0071
S-adenosyl-L-homocysteine
pH 7.5, 30ưC, cosubstrate: N-deacetylisoipecoside
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0.194
7-O-methyl-N-deacetylisoipecoside
pH 7.5, 30ưC
0.0035
cephaeline
pH 7.5, 30ưC
0.106
N-deacetylisoipecoside
pH 7.5, 30ưC
0.169
S-adenosyl-L-homocysteine
pH 7.5, 30ưC, cosubstrate: N-deacetylisoipecoside
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8
6-methylation of N-deacetylisoipecoside
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30
assay at
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UniProt
brenda
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brenda
i.e. Psychotria ipecacuanha
UniProt
brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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metabolism
CiOMT2 catalyzes the penultimate step, 7-O'-methylation, in emetine biosynthesis, the recombinant CiOMT2 also the last step, synthesis of emetine by 6'-O-methylation, pathway overview
metabolism
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OMT1 catalyzes a step in the biosynthesis of Ipecac alkaloids, pathways overview
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D3KY98_9GENT
350
0
38723
TrEMBL
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E7FL15_9GENT
350
0
39081
TrEMBL
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38700
x * 38700, calculated from sequence
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?
x * 38700, calculated from sequence
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N-terminal His-tagged IpeOMT1 enzyme
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expression in Escherichia coli
OMT2, DNA and amino acid sequence determination and analysis, phylogenetic tree, expression in Escherichia coli strain BL21(DE3)
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Cheong, B.E.; Takemura, T.; Yoshimatsu, K.; Sato, F.
Molecular cloning of an O-methyltransferase from adventitious roots of Carapichea ipecacuanha
Biosci. Biotechnol. Biochem.
75
107-113
2011
Carapichea ipecacuanha (E7FL15)
brenda
Nomura, T.; Kutchan, T.M.
Three new O-methyltransferases are sufficient for all O-methylation reactions of ipecac alkaloid biosynthesis in root culture of Psychotria ipecacuanha
J. Biol. Chem.
285
7722-7738
2010
Carapichea ipecacuanha (D3KY98), Carapichea ipecacuanha
brenda
Nomura, T.; Kutchan, T.M.
Is a metabolic enzyme complex involved in the efficient and accurate control of Ipecac alkaloid biosynthesis in Psychotria ipecacuanha?
Plant Signal. Behav.
5
875-877
2010
Carapichea ipecacuanha
brenda
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