A polyketide synthase catalysing the first committed step in the cannabinoids biosynthetic pathway of the plant Cannabis sativa. The enzyme was previously thought to also function as a cyclase, but the cyclization is now known to be catalysed by EC 4.4.1.26, olivetolic acid cyclase.
A polyketide synthase catalysing the first committed step in the cannabinoids biosynthetic pathway of the plant Cannabis sativa. The enzyme was previously thought to also function as a cyclase, but the cyclization is now known to be catalysed by EC 4.4.1.26, olivetolic acid cyclase.
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
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
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
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
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
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
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
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
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
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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DISEASE
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LINK TO PUBMED
Dehydration
PpORS, an ancient type III polyketide synthase, is required for integrity of leaf cuticle and resistance to dehydration in the moss, Physcomitrella patens.
Crystallization and preliminary X-ray crystallographic investigations of an unusual type III polyketide synthase PKS18 from Mycobacterium tuberculosis.
analysis of the transcriptome of glandular trichomes from female cannabis flowers for type III PKS activity, the primary site of cannabinoid biosynthesis
no enzyme activity in seedlings, fruits, and roots. Neither cannabinoid acids nor their decarboxylated forms are found in seedlings and roots in the four varieties of cannabis plants. Accumulation of cannabinoids in bracts during the growth and development of glandular trichomes from flowers
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
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
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
the enzyme is involved the biosynthesis of the first precursor of cannabinoids, olivetolic acid. Cannabinoid and flavonoid profiling, overview. Accumulation of cannabinoids in bracts during the growth and development of glandular trichomes from flowers, cannabinoid accumulation iscorrelated with maximum activities for an olivetol-forming PKS, developmental and defens-related regulation of cannabinoid pathway enzymes, overview
olivetolic acid is the first intermediate involved in the cannabinoid biosynthesis in Cannabis sativa leading to the acidic forms of the major cannabinoids such as DELTA9-tetrahydrocannabinolic acid and cannabinolic acid
polyketide synthases play an important role in the biosynthesis of secondary metabolites such as resveratrol, a candidate for cancer chemoprevention and naringenin, the precursor for flavonoids. Olivetolic acid is also be expected to be synthesized by a PKS
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
polyketide synthases play an important role in the biosynthesis of secondary metabolites such as resveratrol, a candidate for cancer chemoprevention and naringenin, the precursor for flavonoids. Olivetolic acid is also be expected to be synthesized by a PKS
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CRYSTALLIZATION (Commentary)
ORGANISM
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LITERATURE
cocrystallization of the enzyme with CoA (2 mM) is performed in 0.2 M potassium nitrate containing 20% w/v PEG 3350 for 72 h at 4 °C using the sitting drop vapour diffusion technique. Crystals are cryo-protected in the mother liquor containing 20% glycerol, followed by flash freezing in liquid nitrogen
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
a synthetic pathway for the production of olivetolic acid in Escherichia coli is developed. Through combining OLA synthase and OLA cyclase expression with the required modules of a beta-oxidation reversal for hexanoyl-CoAgeneration, we demonstrate the in vivo synthesis of olivetolic acid from a single carbon source. The integration of additional auxiliary enzymes to increase hexanoyl-CoA and malonyl-CoA, along with evaluation of varying fermentation conditions enabled the synthesis of 80 mg/l olivetolic acid. Olivetolic acid has various pharmacological activities