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Literature summary extracted from

  • Taura, F.; Tanaka, S.; Taguchi, C.; Fukamizu, T.; Tanaka, H.; Shoyama, Y.; Morimoto, S.
    Characterization of olivetol synthase, a polyketide synthase putatively involved in cannabinoid biosynthetic pathway (2009), FEBS Lett., 583, 2061-2066.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.3.1.206 recombinant expression of the C-terminally His-tagged enzyme Cannabis sativa

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.3.1.206 0.0569 0.0631 hexanoyl-CoA pH 5.5, 30°C, dependent on product formed Cannabis sativa
2.3.1.206 0.0861 0.0889 butyryl-CoA pH 5.5, 30°C, dependent on product formed Cannabis sativa

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
2.3.1.206 42585
-
 2 * 42585, sequence calculation, 2 x 44000, recombinant C-terminally His-tagged enzyme, SDS-PAGE Cannabis sativa
2.3.1.206 89000
-
 recombinant C-terminally His-tagged enzyme, gel filtration Cannabis sativa

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
-
 3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
-
 ?

Organism

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

Purification (Commentary)

EC Number Purification (Comment) Organism
2.3.1.206 recombinant C-terminally His-tagged enzyme by nickel affinity chromatography Cannabis sativa

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.3.1.206 flower
-
 Cannabis sativa
-
2.3.1.206 leaf young and rapidly expanding Cannabis sativa
-
2.3.1.206 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
-
2.3.1.206 root
-
 Cannabis sativa
-
2.3.1.206 stem
-
 Cannabis sativa
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
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 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 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

EC Number Subunits Comment Organism
2.3.1.206 dimer 2 * 42585, sequence calculation, 2 x 44000, recombinant C-terminally His-tagged enzyme, SDS-PAGE Cannabis sativa

Synonyms

EC Number Synonyms Comment Organism
2.3.1.206 olivetol synthase
-
 Cannabis sativa
2.3.1.206 OLS
-
 Cannabis sativa

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.3.1.206 30
-
 assay at Cannabis sativa

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.3.1.206 0.011 0.012 butyryl-CoA pH 5.5, 30°C, dependent on product formed Cannabis sativa
2.3.1.206 0.018 0.058 hexanoyl-CoA pH 5.5, 30°C, dependent on product formed Cannabis sativa

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.3.1.206 5.5
-
 assay at Cannabis sativa

General Information

EC Number General Information Comment Organism
2.3.1.206 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]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
2.3.1.206 0.129 0.134 butyryl-CoA pH 5.5, 30°C, dependent on product formed Cannabis sativa
2.3.1.206 0.28 1.013 hexanoyl-CoA pH 5.5, 30°C, dependent on product formed Cannabis sativa