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Literature summary for 2.3.1.206 extracted from
- Characterization of olivetol synthase, a polyketide synthase putatively involved in cannabinoid biosynthetic pathway (2009), FEBS Lett., 583, 2061-2066.
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| recombinant expression of the C-terminally His-tagged enzyme | Cannabis sativa |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.0569 | 0.0631 | hexanoyl-CoA | pH 5.5, 30°C, dependent on product formed | Cannabis sativa |  |
| 0.0861 | 0.0889 | butyryl-CoA | pH 5.5, 30°C, dependent on product formed | Cannabis sativa | |
Molecular Weight [Da]
| Molecular Weight [Da] | Molecular Weight Maximum [Da] | Comment | Organism |
|---|---|---|---|
| 42585 | - |
2 * 42585, sequence calculation, 2 x 44000, recombinant C-terminally His-tagged enzyme, SDS-PAGE | Cannabis sativa |
| 89000 | - |
recombinant C-terminally His-tagged enzyme, gel filtration | Cannabis sativa |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| 3 malonyl-CoA + hexanoyl-CoA | Cannabis sativa | - |
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2 | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Cannabis sativa | - |
- |
- |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
| recombinant C-terminally His-tagged enzyme by nickel affinity chromatography | Cannabis sativa |
Source Tissue
| Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|
| flower | - |
Cannabis sativa | - |
| leaf | young and rapidly expanding | Cannabis sativa | - |
| additional information | the native olivetol synthase is expressed in the cannabinoid-producing tissues as a catalytically active enzyme whereas olivetolic acid-producing activity is not detected in any samples | Cannabis sativa | - |
| root | - |
Cannabis sativa | - |
| stem | - |
Cannabis sativa | - |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| 3 malonyl-CoA + butyryl-CoA | - |
Cannabis sativa | ? | formation of resorcinol | ? | |
| 3 malonyl-CoA + hexanoyl-CoA | - |
Cannabis sativa | 3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2 | - |
? | |
| 3 malonyl-CoA + hexanoyl-CoA | the olivetol sythase is specific to hexanoyl-CoA, it catalyzes aldol condensation and catalyzes the formation of olivetol, 5-pentyl-1,3-benzenediol, the decarboxylated form of olivetolic acid. Olivetol may be an artifact of in vitro enzyme assays because olivetol is not detected in Cannabis tissues | Cannabis sativa | 3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2 | - |
? | |
| additional information | besides hexanoyl-CoA, the enzyme accepts starter CoA esters with C4 to C8 side chains such as butyryl-, isovaleryl-, and octanoyl-CoA, it produces triketide pyrones from these substrates except affording 5-propylresorcinol, i.e. divarinol, from butyryl-CoA with a lower kcat/Km value than that for olivetol formation, substrate specificity and product formation of triketide pyrone, tetraketide pyrone, and resorcinol, overview. The enzyme does not catalyze any reactions from aromatic CoA esters including 4-coumaroyl-CoA. Olivetol may be an artifact of in vitro enzyme assays because olivetol is not detected in Cannabis tissues | Cannabis sativa | ? | - |
? | |
Subunits
| Subunits | Comment | Organism |
|---|---|---|
| dimer | 2 * 42585, sequence calculation, 2 x 44000, recombinant C-terminally His-tagged enzyme, SDS-PAGE | Cannabis sativa |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| olivetol synthase | - |
Cannabis sativa |
| OLS | - |
Cannabis sativa |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 30 | - |
assay at | Cannabis sativa |
Turnover Number [1/s]
| Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.011 | 0.012 | butyryl-CoA | pH 5.5, 30°C, dependent on product formed | Cannabis sativa | |
| 0.018 | 0.058 | hexanoyl-CoA | pH 5.5, 30°C, dependent on product formed | Cannabis sativa | |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 5.5 | - |
assay at | Cannabis sativa |
General Information
| General Information | Comment | Organism |
|---|---|---|
| additional information | factors might affect the timing of the hydrolysis and cyclization reactions by olivetol synthase to form an olivetolic acid-forming metabolic complex together with olivetol synthase, metabolon formation | Cannabis sativa |
kcat/KM [mM/s]
| kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.129 | 0.134 | butyryl-CoA | pH 5.5, 30°C, dependent on product formed | Cannabis sativa | |
| 0.28 | 1.013 | hexanoyl-CoA | pH 5.5, 30°C, dependent on product formed | Cannabis sativa | |
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