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Literature summary extracted from

  • Gagne, S.; Stout, J.; Liu, E.; Boubakir, Z.; Clark, S.; Page, J.
    Identification of olivetolic acid cyclase from Cannabis sativa reveals a unique catalytic route to plant polyketides (2012), Proc. Natl. Acad. Sci. USA, 109, 12811-12816.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.3.1.206 expression of TKS in Escherichia coli, transient co-expression of fluorescent-labeled TKS and OAC in Nicotiana benthamiana leaves shows that TKS and OAC, which lack predicted signal peptides, are both localized to the cytoplasm. Yeast cultures expressing TKS and OAC and fed sodium hexanoate produce olivetolic acid and olivetol in the medium but no alpha-pyrones Cannabis sativa
4.4.1.26 expressed in Escherichia coli Cannabis sativa

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.3.1.206 additional information
-
 additional information no allosteric regulation of TKS Cannabis sativa

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
2.3.1.206 cytoplasm
-
 Cannabis sativa 5737
-
4.4.1.26 cytoplasm
-
 Cannabis sativa 5737
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.3.1.206 3 malonyl-CoA + hexanoyl-CoA Cannabis sativa reaction of tetraketide synthase, TKS 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 additional information Cannabis sativa tetraketide synthase produces olivetol from the C12 polyketide intermediate, while olivetolic acid cyclase produces olivetolic acid, overview ?
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.206 Cannabis sativa
-
-
-
4.4.1.26 Cannabis sativa I6WU39
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
4.4.1.26 Talon resin column chromatography Cannabis sativa

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.3.1.206 flower analysis of the transcriptome of glandular trichomes from female cannabis flowers for type III PKS activity, the primary site of cannabinoid biosynthesis Cannabis sativa
-
2.3.1.206 additional information OAC transcript is present at high levels in glandular trichomes, an expression profile that parallels other cannabinoid pathway enzymes Cannabis sativa
-
4.4.1.26 glandular trichome
-
 Cannabis sativa
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
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 additional information tetraketide synthase produces olivetol from the C12 polyketide intermediate, while olivetolic acid cyclase produces olivetolic acid, overview Cannabis sativa ?
-
 ?
2.3.1.206 additional information recombinant TKS enzyme produces triketide, pentyl diacetic acid lactone, and tetraketide, hexanoyl triacetic acid lactone, and olivetol in vitro Cannabis sativa ?
-
 ?
4.4.1.26 3,5,7-trioxododecanoyl-CoA
-
 Cannabis sativa olivetolic acid + CoA
-
 ?
4.4.1.26 additional information the enzyme has no intrinsic polyketide synthase activity and does not convert hexanoyl triacetic acid lactone to olivetolic acid Cannabis sativa ?
-
 ?

Subunits

EC Number Subunits Comment Organism
4.4.1.26 dimer
-
 Cannabis sativa

Synonyms

EC Number Synonyms Comment Organism
2.3.1.206 tetraketide synthase
-
 Cannabis sativa
2.3.1.206 TKS
-
 Cannabis sativa
2.3.1.206 type III PKS
-
 Cannabis sativa
2.3.1.206 type III polyketide synthase
-
 Cannabis sativa
4.4.1.26 OAC
-
 Cannabis sativa

General Information

EC Number General Information Comment Organism
2.3.1.206 metabolism the enzyme is involved in the biosynthesis of cannabinoids, the glandular trichomes from female cannabis flowers are the primary site of cannabinoid biosynthesis, proposed cannabinoid biosynthetic pathway, overview. TKS synthesizes a diffusible intermediate that is converted to olivetolic acid by OAC Cannabis sativa
2.3.1.206 physiological function the type III PKS, i.e. tetraketide synthase, from cannabis trichomes requires the presence of a polyketide cyclase enzyme, olivetolic acid cyclase, which catalyzes a C2-C7 intramolecular aldol condensation with carboxylate retention to form olivetolic acid. No physical interaction of TKS and OAC. Polyketide cyclases may play a role in generating plant chemical diversity Cannabis sativa