EC Number |
Substrates |
Organism |
Products |
Reversibility |
---|
2.3.1.206 | 3 malonyl-CoA + butyryl-CoA |
- |
Cannabis sativa |
? |
formation of resorcinol |
? |
2.3.1.206 | 3 malonyl-CoA + hexanoyl-CoA |
- |
Cannabis sativa |
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2 |
- |
? |
2.3.1.206 | 3 malonyl-CoA + hexanoyl-CoA |
- |
Cannabis sativa |
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2 |
formation of olivetol via C12-polyketide, no formation of olivetolic acid, product identification by its UV-spectrum, mass spectrometry analysis and comparison with reference compound |
? |
2.3.1.206 | 3 malonyl-CoA + hexanoyl-CoA |
- |
Cannabis sativa |
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2 |
formation of olivetolic acid |
? |
2.3.1.206 | 3 malonyl-CoA + hexanoyl-CoA |
- |
Cannabis sativa |
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2 |
formation of olivetol via C12-polyketide by condensation and cyclization reactions, stilbene synthase like mechanism, overview. No formation of olivetolic acid, UV-spectrum and mass spectrometry analysis |
? |
2.3.1.206 | 3 malonyl-CoA + hexanoyl-CoA |
reaction of tetraketide synthase, TKS |
Cannabis sativa |
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2 |
- |
? |
2.3.1.206 | 3 malonyl-CoA + hexanoyl-CoA |
reaction of tetraketide synthase, TKS |
Cannabis sativa |
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2 |
the C12-polyketide intermediate of the olivetol or olivetolic acid synthesis, olivetolic acid is the precursor for cannabinoid synthesis |
? |
2.3.1.206 | 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 |
- |
? |
2.3.1.206 | 3 malonyl-CoA + hexanoyl-CoA |
in the absence of olivetolic acid cyclase (OAC), a nonenzymatic C2 -> C7 decarboxylative aldol condensation of the tetraketide intermediate occurs forming olivetol. The apparent plasticity of the enzyme with only minor alterations in amino acid sequences demonstrates the subtle nature of the mechanistic discrimination. This involves interplay between multiple residues, an inherently flexible active site designed to accommodate a growing scaffold and easily convertible cyclization mechanism(s) with minimal intervention |
Cannabis sativa |
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2 |
- |
? |
2.3.1.206 | 3 malonyl-CoA + hexanoyl-CoA |
formation of a C12-polyketide, which is formed to olivetol and its carboxylated derivative olivetolic acid by an aldol reaction thrugh stilbene carboxylate synthase-like activity, overview |
Cannabis sativa |
? |
- |
? |