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Literature summary for 2.1.1.117 extracted from
- Unraveling additional O-methylation steps in benzylisoquinoline alkaloid biosynthesis in California poppy (Eschscholzia californica) (2017), Plant Cell Physiol., 58, 1528-1540 .
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| 2-mercaptoethanol | 5 mM, 9% inhibition | Eschscholzia californica subsp. californica |  |
| Ca2+ | 5 mM, 7% inhibition | Eschscholzia californica subsp. californica | |
| Co2+ | 5 mM, 9% inhibition | Eschscholzia californica subsp. californica | |
| Cu2+ | 5 mM, 21% inhibition | Eschscholzia californica subsp. californica | |
| additional information | not inhibitory: Mg2+, Mn2+, Fe2+ | Eschscholzia californica subsp. californica | |
| Ni2+ | 5 mM, 18% inhibition | Eschscholzia californica subsp. californica | |
| Zn2+ | 5 mM, 20% inhibition | Eschscholzia californica subsp. californica | |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.0093 | - |
S-adenosyl-L-methionine | cosubstrate (S)-scoulerine, product (S)-tetrahydrocolumbamine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.0145 | - |
S-adenosyl-L-methionine | cosubstrate (S)-reticuline, product codamine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.0157 | - |
S-adenosyl-L-methionine | cosubstrate (S)-reticuline, product norlaudanine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.0219 | - |
(S)-scoulerine | product 2-O-methylscoulerine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.0245 | - |
(S)-scoulerine | product (S)-tetrahydrocolumbamine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.0288 | - |
S-adenosyl-L-methionine | cosubstrate (S)-scoulerine, product 2-O-methylscoulerine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.0382 | - |
(S)-norreticuline | product norlaudanine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.119 | - |
S-adenosyl-L-methionine | cosubstrate (S)-reticuline, product laudanine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.187 | - |
(S)-reticuline | product codamine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.393 | - |
(S)-reticuline | product laudanine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
Metals/Ions
| Metals/Ions | Comment | Organism | Structure |
|---|---|---|---|
| additional information | divalent cations are not required | Eschscholzia californica subsp. californica |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Eschscholzia californica subsp. californica | A0A224ALZ8 | - |
- |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| additional information | enzyme is a scoulerine-9-O-methyltransferase for the biosynthesis of chelerythrine in California poppy, it produces 7-O-methylated, 3'-O-methylated and dual O-methylated products from reticuline and norreticuline, and 9-O-methylated tetrahydrocolumbamine, 2-O-methylscoulerine and tetrahydropalmatine from scoulerine | Eschscholzia californica subsp. californica | ? | - |
- |
|
| S-adenosyl-L-methionine + (S)-norreticuline | - |
Eschscholzia californica subsp. californica | S-adenosyl-L-homocysteine + norcodamine + norlaudanine | - |
? | |
| S-adenosyl-L-methionine + (S)-reticuline | - |
Eschscholzia californica subsp. californica | S-adenosyl-L-homocysteine + codamine + laudanine | - |
? | |
| S-adenosyl-L-methionine + (S)-scoulerine | - |
Eschscholzia californica subsp. californica | S-adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine + 2-O-methylscoulerine + tetrahydropalmatine | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| scoulerine/reticuline O-methyltransferase | - |
Eschscholzia californica subsp. californica |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 35 | - |
- |
Eschscholzia californica subsp. californica |
Turnover Number [1/s]
| Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.01 | - |
S-adenosyl-L-methionine | cosubstrate (S)-reticuline, product norlaudanine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.01 | - |
S-adenosyl-L-methionine | cosubstrate (S)-scoulerine, product (S)-tetrahydrocolumbamine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.01 | - |
S-adenosyl-L-methionine | cosubstrate (S)-scoulerine, product 2-O-methylscoulerine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.01 | - |
(S)-scoulerine | product 2-O-methylscoulerine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.01 | - |
(S)-norreticuline | product norlaudanine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.02 | - |
(S)-scoulerine | product (S)-tetrahydrocolumbamine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.05 | - |
(S)-reticuline | product codamine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.08 | - |
S-adenosyl-L-methionine | cosubstrate (S)-reticuline, product codamine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.12 | - |
S-adenosyl-L-methionine | cosubstrate (S)-reticuline, product laudanine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.24 | - |
(S)-reticuline | product laudanine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 8.4 | - |
- |
Eschscholzia californica subsp. californica |
pH Range
| pH Minimum | pH Maximum | Comment | Organism |
|---|---|---|---|
| 6.8 | 9.6 | - |
Eschscholzia californica subsp. californica |
kcat/KM [mM/s]
| kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.26 | - |
(S)-norreticuline | product norlaudanine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.27 | - |
(S)-reticuline | product codamine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.35 | - |
S-adenosyl-L-methionine | cosubstrate (S)-scoulerine, product 2-O-methylscoulerine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.46 | - |
(S)-scoulerine | product 2-O-methylscoulerine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.61 | - |
(S)-reticuline | product laudanine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.64 | - |
S-adenosyl-L-methionine | cosubstrate (S)-reticuline, product norlaudanine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 0.82 | - |
(S)-scoulerine | product (S)-tetrahydrocolumbamine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 1 | - |
S-adenosyl-L-methionine | cosubstrate (S)-reticuline, product laudanine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 1.07 | - |
S-adenosyl-L-methionine | cosubstrate (S)-scoulerine, product (S)-tetrahydrocolumbamine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
| 5.5 | - |
S-adenosyl-L-methionine | cosubstrate (S)-reticuline, product codamine, pH 8.4, 35°C | Eschscholzia californica subsp. californica | |
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