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Literature summary for 4.2.1.78 extracted from
- Isolation and partial characterization of norcoclaurine synthase, the first committed step in benzylisoquinoline alkaloid biosynthesis, from opium poppy (2001), Planta, 213, 898-906.
Activating Compound
| Activating Compound | Comment | Organism | Structure |
|---|---|---|---|
| fungal elicitor of Bortrytis sp. | isolated elicitor induces the enzyme activity in cell suspension culture 20fold | Papaver somniferum | |
| additional information | enzyme is not affected by Mg2+ and Ca2+ | Papaver somniferum |
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| additional information | no inhibition by several benzylisochinoline alkaloids, enzyme is not affected by Mg2+ and Ca2+ | Papaver somniferum |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| additional information | - |
additional information | kinetics, sigmoidal saturation kinetics for dopamine, Hill coeffcient 1.84, cooperativity between the dopamine binding sites on each subunit | Papaver somniferum | |
| additional information | - |
additional information | kinetics, sigmoidal saturation kinetics for dopamine, Hill coeffcient 2.16, cooperativity between the dopamine binding sites on each subunit | Thalictrum flavum ssp. glaucum | |
| additional information | - |
additional information | kinetics, sigmoidal saturation kinetics for dopamine, Hill coeffcient 2.19, cooperativity between the dopamine binding sites on each subunit | Eschscholzia californica | |
| 0.42 | - |
4-hydroxyphenylacetaldehyde | pH 7.0, 37°C, hyperbolic saturation kinetics | Thalictrum flavum ssp. glaucum |  |
| 0.66 | - |
4-hydroxyphenylacetaldehyde | pH 7.0, 37°C, hyperbolic saturation kinetics | Eschscholzia californica | |
| 1 | - |
4-hydroxyphenylacetaldehyde | pH 7.0, 37°C, hyperbolic saturation kinetics | Papaver somniferum | |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde | Eschscholzia californica | first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux | (S)-Norcoclaurine + H2O | - |
ir | |
| 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde | Papaver somniferum | first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux | (S)-Norcoclaurine + H2O | - |
ir | |
| 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde | Thalictrum flavum ssp. glaucum | first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux | (S)-Norcoclaurine + H2O | - |
ir | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Eschscholzia californica | - |
- |
- |
| no activity in Catharanthus roseus | - |
- |
- |
| no activity in Nicotiana tabacum | - |
- |
- |
| Papaver somniferum | - |
cv. Marianne | - |
| Thalictrum flavum ssp. glaucum | - |
- |
- |
Reaction
| Reaction | Comment | Organism | Reaction ID |
|---|---|---|---|
| 4-hydroxyphenylacetaldehyde + dopamine = (S)-norcoclaurine + H2O | the reaction makes a six-membered ring by forming a bond between C-6 of the 3,4-dihydroxyphenyl group of the dopamine and C-1 of the aldehyde in the imine formed between the substrates, the product is the precursor of the benzylisoquinoline alkaloids in plants, the enzyme, formerly known as (S)-norleudanosoline synthase, will also catalyse the reaction of 4-(2-aminoethyl)benzene-1,2-diol + (di-3,4-hydroxyphenyl)acetaldehyde to form (S)-norlaudanosoline, but this alkaloid has not been found to occur in plants, cooperativity between substrate binding sites | Eschscholzia californica | |
| 4-hydroxyphenylacetaldehyde + dopamine = (S)-norcoclaurine + H2O | the reaction makes a six-membered ring by forming a bond between C-6 of the 3,4-dihydroxyphenyl group of the dopamine and C-1 of the aldehyde in the imine formed between the substrates, the product is the precursor of the benzylisoquinoline alkaloids in plants, the enzyme, formerly known as (S)-norleudanosoline synthase, will also catalyse the reaction of 4-(2-aminoethyl)benzene-1,2-diol + (di-3,4-hydroxyphenyl)acetaldehyde to form (S)-norlaudanosoline, but this alkaloid has not been found to occur in plants, cooperativity between substrate binding sites | Papaver somniferum | |
| 4-hydroxyphenylacetaldehyde + dopamine = (S)-norcoclaurine + H2O | the reaction makes a six-membered ring by forming a bond between C-6 of the 3,4-dihydroxyphenyl group of the dopamine and C-1 of the aldehyde in the imine formed between the substrates, the product is the precursor of the benzylisoquinoline alkaloids in plants, the enzyme, formerly known as (S)-norleudanosoline synthase, will also catalyse the reaction of 4-(2-aminoethyl)benzene-1,2-diol + (di-3,4-hydroxyphenyl)acetaldehyde to form (S)-norlaudanosoline, but this alkaloid has not been found to occur in plants, cooperativity between substrate binding sites | Thalictrum flavum ssp. glaucum |
Source Tissue
| Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|
| cell suspension culture | - |
Eschscholzia californica | - |
| cell suspension culture | - |
Papaver somniferum | - |
| cell suspension culture | - |
Thalictrum flavum ssp. glaucum | - |
| plant | all organs especially in root and stem | Papaver somniferum | - |
| root | highest activity level | Papaver somniferum | - |
| seed | germinating | Papaver somniferum | - |
| seedling | - |
Papaver somniferum | - |
| stem | - |
Papaver somniferum | - |
Storage Stability
| Storage Stability | Organism |
|---|---|
| -80°C, purified enzyme, 7 days, no loss of activity | Papaver somniferum |
| 4°C, purified enzyme, 7 days, 75% loss of activity | Papaver somniferum |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde | 4-(2-aminoethyl)benzene-1,2-diol is dopmaine | Eschscholzia californica | (S)-Norcoclaurine + H2O | - |
ir | |
| 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde | 4-(2-aminoethyl)benzene-1,2-diol is dopmaine | Papaver somniferum | (S)-Norcoclaurine + H2O | - |
ir | |
| 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde | 4-(2-aminoethyl)benzene-1,2-diol is dopmaine | Thalictrum flavum ssp. glaucum | (S)-Norcoclaurine + H2O | - |
ir | |
| 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde | first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux | Eschscholzia californica | (S)-Norcoclaurine + H2O | - |
ir | |
| 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde | first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux | Papaver somniferum | (S)-Norcoclaurine + H2O | - |
ir | |
| 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde | first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux | Thalictrum flavum ssp. glaucum | (S)-Norcoclaurine + H2O | - |
ir | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| NCS | - |
Eschscholzia californica |
| NCS | - |
Papaver somniferum |
| NCS | - |
Thalictrum flavum ssp. glaucum |
| norcoclaurine synthase | - |
Eschscholzia californica |
| norcoclaurine synthase | - |
Papaver somniferum |
| norcoclaurine synthase | - |
Thalictrum flavum ssp. glaucum |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 45 | 55 | - |
Eschscholzia californica |
| 45 | 55 | - |
Thalictrum flavum ssp. glaucum |
| 50 | - |
- |
Papaver somniferum |
Temperature Range [°C]
| Temperature Minimum [°C] | Temperature Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 37 | 57 | half-maximal activities at 37°C and 57°C | Papaver somniferum |
Temperature Stability [°C]
| Temperature Stability Minimum [°C] | Temperature Stability Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 55 | - |
instable above 55°C | Papaver somniferum |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 6.5 | 7 | - |
Eschscholzia californica |
| 6.5 | 7 | - |
Papaver somniferum |
| 6.5 | 7 | - |
Thalictrum flavum ssp. glaucum |
pH Range
| pH Minimum | pH Maximum | Comment | Organism |
|---|---|---|---|
| 6.2 | 9 | 50% of maximal activity at pH 6.2, 68% of maximal activity at pH 9.0 | Papaver somniferum |
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Release 2023.1 (January 2023)
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