2.3.1.206: 3,5,7-trioxododecanoyl-CoA synthase
This is an abbreviated version!
For detailed information about 3,5,7-trioxododecanoyl-CoA synthase, go to the full flat file.
Word Map on EC 2.3.1.206
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2.3.1.206
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starter
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chalcone
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pyrones
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triketide
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condensations
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alkylresorcinols
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4-coumaroyl-coa
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1,3,6,8-tetrahydroxynaphthalene
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pentaketide
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resorcinol
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cys-his-asn
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benzalacetone
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octaketide
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flaviolin
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chs-like
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huperzia
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alpha-pyrones
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olivetolic
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arborescens
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hexaketide
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resorcylic
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coa-linked
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precursor-directed
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n-methylanthraniloyl-coa
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synthesis
- 2.3.1.206
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starter
- chalcone
- pyrones
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triketide
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condensations
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alkylresorcinols
- 4-coumaroyl-coa
- 1,3,6,8-tetrahydroxynaphthalene
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pentaketide
- resorcinol
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cys-his-asn
- benzalacetone
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octaketide
- flaviolin
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chs-like
- huperzia
- alpha-pyrones
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olivetolic
- arborescens
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hexaketide
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resorcylic
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coa-linked
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precursor-directed
- n-methylanthraniloyl-coa
- synthesis
Reaction
3 malonyl-CoA + = 3 CoA + + 3 CO2
Synonyms
OLA synthase, olivetol synthase, olivetol-forming PKS, OLS, PKS, polyketide synthase, tetraketide synthase, TKS, type III PKS, type III polyketide synthase
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Substrates Products
Substrates Products on EC 2.3.1.206 - 3,5,7-trioxododecanoyl-CoA synthase
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REACTION DIAGRAM
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
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3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
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3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
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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
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3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
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formation of olivetolic acid
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3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
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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
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3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
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reaction of tetraketide synthase, TKS
the C12-polyketide intermediate of the olivetol or olivetolic acid synthesis, olivetolic acid is the precursor for cannabinoid synthesis
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3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
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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
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3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
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
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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
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3 malonyl-CoA + hexanoyl-CoA
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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
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no formation of olivetol by an enzymatic or chemical decarboxylation from olivetolic acid, cannabinoid profiling, overview
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additional information
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tetraketide synthase produces olivetol from the C12 polyketide intermediate, while olivetolic acid cyclase produces olivetolic acid, overview
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additional information
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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
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additional information
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recombinant TKS enzyme produces triketide, pentyl diacetic acid lactone, and tetraketide, hexanoyl triacetic acid lactone, and olivetol in vitro
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additional information
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usage of 4-coumaroyl-CoA and malonyl-CoA as substrates, resulting product is naringenin, not resveratrol. The enzyme might show a broad specificity of substrate including aliphatic substrates such as isovaleryl-CoA, isobutyryl-CoA, and n-hexanoyl-CoA
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additional information
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usage of 4-coumaroyl-CoA and malonyl-CoA as substrates, resulting product is naringenin, not resveratrol. The enzyme might show a broad specificity of substrate including aliphatic substrates such as isovaleryl-CoA, isobutyryl-CoA, and n-hexanoyl-CoA
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