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Information on EC 2.3.1.206 - 3,5,7-trioxododecanoyl-CoA synthase
for references in articles please use BRENDA:EC2.3.1.206
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EC Tree 2 Transferases
2.3 Acyltransferases
2.3.1 Transferring groups other than aminoacyl groups
2.3.1.206 3,5,7-trioxododecanoyl-CoA synthase
IUBMB Comments
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.
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
- 2.3.1.206
-
starter
- chalcone
- pyrones
-
triketide
-
condensations
-
alkylresorcinols
- 4-coumaroyl-coa
- 1,3,6,8-tetrahydroxynaphthalene
-
pentaketide
- resorcinol
-
cys-his-asn
- benzalacetone
-
octaketide
- flaviolin
-
chs-like
- huperzia
- alpha-pyrones
-
olivetolic
- arborescens
-
hexaketide
-
resorcylic
-
coa-linked
-
precursor-directed
- n-methylanthraniloyl-coa
- synthesis
showSynonyms
type iii pks, type iii polyketide synthase, olivetol synthase, tetraketide synthase, ola synthase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
OLS
polyketide synthase
tetraketide synthase
TKS
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
3 malonyl-CoA + hexanoyl-CoA = 3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
malonyl-CoA:hexanoyl-CoA malonyltransferase (3,5,7-trioxododecanoyl-CoA-forming)
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.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
3 malonyl-CoA + butyryl-CoA
?
-
Substrates: -
Products: formation of resorcinol
Products: formation of resorcinol
?
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
-
Substrates: -
Products: -
Products: -
?
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
-
Substrates: -
Products: formation of olivetolic acid
Products: formation of olivetolic acid
?
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
-
Substrates: -
Products: 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
Products: 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
?
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
-
Substrates: reaction of tetraketide synthase, TKS
Products: the C12-polyketide intermediate of the olivetol or olivetolic acid synthesis, olivetolic acid is the precursor for cannabinoid synthesis
Products: the C12-polyketide intermediate of the olivetol or olivetolic acid synthesis, olivetolic acid is the precursor for cannabinoid synthesis
?
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
-
Substrates: 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
Products: -
Products: -
?
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
-
Substrates: -
Products: 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
Products: 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
?
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
-
Substrates: reaction of tetraketide synthase, TKS
Products: -
Products: -
?
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
Substrates: -
Products: -
Products: -
?
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
Substrates: 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
Products: -
Products: -
?
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
Substrates: -
Products: -
Products: -
?
3 malonyl-CoA + hexanoyl-CoA
?
-
Substrates: 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
Products: -
Products: -
?
3 malonyl-CoA + hexanoyl-CoA
?
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
-
Substrates: no formation of olivetol by an enzymatic or chemical decarboxylation from olivetolic acid, cannabinoid profiling, overview
Products: -
Products: -
?
additional information
?
-
-
Substrates: tetraketide synthase produces olivetol from the C12 polyketide intermediate, while olivetolic acid cyclase produces olivetolic acid, overview
Products: -
Products: -
?
additional information
?
-
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
-
Substrates: recombinant TKS enzyme produces triketide, pentyl diacetic acid lactone, and tetraketide, hexanoyl triacetic acid lactone, and olivetol in vitro
Products: -
Products: -
?
additional information
?
-
-
Substrates: 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
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
-
Substrates: -
Products: -
Products: -
?
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
-
Substrates: -
Products: formation of olivetolic acid
Products: formation of olivetolic acid
?
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
-
Substrates: -
Products: 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
Products: 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
?
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
-
Substrates: reaction of tetraketide synthase, TKS
Products: the C12-polyketide intermediate of the olivetol or olivetolic acid synthesis, olivetolic acid is the precursor for cannabinoid synthesis
Products: the C12-polyketide intermediate of the olivetol or olivetolic acid synthesis, olivetolic acid is the precursor for cannabinoid synthesis
?
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
Substrates: -
Products: -
Products: -
?
additional information
?
-
-
Substrates: no formation of olivetol by an enzymatic or chemical decarboxylation from olivetolic acid, cannabinoid profiling, overview
Products: -
Products: -
?
additional information
?
-
-
Substrates: tetraketide synthase produces olivetol from the C12 polyketide intermediate, while olivetolic acid cyclase produces olivetolic acid, overview
Products: -
Products: -
?
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DISEASE
TITLE OF PUBLICATION
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.
Infertility, Male
OsPKS2 is required for rice male fertility by participating in pollen wall formation.
Tuberculosis
A novel tunnel in mycobacterial type III polyketide synthase reveals the structural basis for generating diverse metabolites.
Tuberculosis
Crystallization and preliminary X-ray crystallographic investigations of an unusual type III polyketide synthase PKS18 from Mycobacterium tuberculosis.
Tuberculosis
Structure function analysis of novel type III polyketide synthases from Arabidopsis thaliana.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
-
no allosteric regulation of TKS
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
-
analysis of the transcriptome of glandular trichomes from female cannabis flowers for type III PKS activity, the primary site of cannabinoid biosynthesis
brenda
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
brenda
additional information
-
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
brenda
additional information
-
no activity in seeds, roots, stems, and lower leaves
brenda
additional information
-
OAC transcript is present at high levels in glandular trichomes, an expression profile that parallels other cannabinoid pathway enzymes
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
physiological function
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
metabolism
-
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
metabolism
-
the polyketide synthase catalyzes the first step of cannabinoid biosynthesis, leading to olivetolic acid
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
physiological function
-
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
physiological function
-
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
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
physiological function
-
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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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
42585
-
2 * 42585, sequence calculation, 2 x 44000, recombinant C-terminally His-tagged enzyme, SDS-PAGE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
-
2 * 42585, sequence calculation, 2 x 44000, recombinant C-terminally His-tagged enzyme, SDS-PAGE
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
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
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
L190G
substitution substantially elongates the active-site cavity, confers the ability to produce up to 3,5,7-trioxohexadecanoyl-CoA
synthesis
expression of Cannabis sativa tetraketide synthase and olivetolic acid cyclase in Phaeodactylum tricornutum enables the production of cannabinoids precursors. Olivetolic acid accumulates to up to 2.6 mg/l, and novel molecules are found
additional information
-
the goal for engineering of zero-cannabinoid plants is knocking out the first step of the biosynthesis catalyzed by the type III PKS enzyme
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant C-terminally His-tagged enzyme by nickel affinity chromatography
-
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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
-
gene pks, cDNA and amino acid sequence determination and analysis, overexpression of His-tagged PKS in Escherichia coli strain M15
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
analysis
synthesis
analysis
-
application of transPACT, a phylogenomic algorithm to automate global classification of trans-AT polyketide synthase modules across bacteria. Polyketide synthases are grouped into PKSs that are conserved in a variety of different producers and putatively responsible for the biosynthesis of identical or closely related polyketides. The second PKS category comprises enzymes that harbor a conserved module block corresponding to a shared polyketide substructure. Thirdly common motifs present only in orphan PKSs may identify biosynthetic diversity in genome mining studies
analysis
-
application of transPACT, a phylogenomic algorithm to automate global classification of trans-AT polyketide synthase modules across bacteria. Polyketide synthases are grouped into PKSs that are conserved in a variety of different producers and putatively responsible for the biosynthesis of identical or closely related polyketides. The second PKS category comprises enzymes that harbor a conserved module block corresponding to a shared polyketide substructure. Thirdly common motifs present only in orphan PKSs may identify biosynthetic diversity in genome mining studies
analysis
-
application of transPACT, a phylogenomic algorithm to automate global classification of trans-AT polyketide synthase modules across bacteria. Polyketide synthases are grouped into PKSs that are conserved in a variety of different producers and putatively responsible for the biosynthesis of identical or closely related polyketides. The second PKS category comprises enzymes that harbor a conserved module block corresponding to a shared polyketide substructure. Thirdly common motifs present only in orphan PKSs may identify biosynthetic diversity in genome mining studies
synthesis
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
synthesis
engineering of Cannabis sativa olivetolic acid cyclase and tetraketide synthase with F24I and L190G substitutions, respectively, in the biosynthesis of DELTA9-THC serves as a platform for the generation of resorcylic acids up to 6-undecylresorcylic acid
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Flores-Sanchez, I.J.; Verpoorte, R.
PKS activities and biosynthesis of cannabinoids and flavonoids in Cannabis sativa L. plants
Plant Cell Physiol.
49
1767-1782
2008
Cannabis sativa
brenda
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
FEBS Lett.
583
2061-2066
2009
Cannabis sativa
brenda
Raharjo, T.; Chang, W.; Verberne, M.; Peltenburg-Looman, A.; Linthorst, H.; Verpoorte, R.
Cloning and over-expression of a cDNA encoding a polyketide synthase from Cannabis sativa
Plant Physiol. Biochem.
42
291-297
2004
Cannabis sativa, Cannabis sativa Four-way
brenda
Raharjo, T.; Chang, W.; Choi, Y.; Peltenburg-Looman, A.; Verpoorte, R.
Olivetol as product of a polyketide synthase in Cannabis sativa L
Plant Sci.
166
381-385
2004
Cannabis sativa
-
brenda
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
Proc. Natl. Acad. Sci. USA
109
12811-12816
2012
Cannabis sativa
brenda
Tan, Z.; Clomburg, J.M.; Gonzalez, R.
Synthetic pathway for the production of olivetolic acid in Escherichia coli
ACS Synth. Biol.
7
1886-1896
2018
Cannabis sativa (B1Q2B6)
brenda
Kearsey, L.J.; Prandi, N.; Karuppiah, V.; Yan, C.; Leys, D.; Toogood, H.; Takano, E.; Scrutton, N.S.
Structure of the Cannabis sativa olivetol-producing enzyme reveals cyclization plasticity in type III polyketide synthases
FEBS J.
287
1511-1524
2019
Cannabis sativa (B1Q2B6)
brenda
Lee, Y.E.; Nakashima, Y.; Kodama, T.; Chen, X.; Morita, H.
Dual engineering of olivetolic acid cyclase and tetraketide synthase to generate longer alkyl-chain olivetolic acid analogs
Org. Lett.
24
410-414
2022
Cannabis sativa (B1Q2B6)
brenda
Awwad, F.; Fantino, E.I.; Heneault, M.; Diaz-Garza, A.M.; Merindol, N.; Custeau, A.; Gelinas, S.E.; Meddeb-Mouelhi, F.; Li, J.; Lemay, J.F.; Karas, B.J.; Desgagne-Penix, I.
Bioengineering of the marine diatom Phaeodactylum tricornutum with cannabis genes enables the production of the cannabinoid precursor, olivetolic acid
Int. J. Mol. Sci.
24
16624
2023
Cannabis sativa (B1Q2B6)
brenda
Helfrich, E.J.N.; Ueoka, R.; Chevrette, M.G.; Hemmerling, F.; Lu, X.; Leopold-Messer, S.; Minas, H.A.; Burch, A.Y.; Lindow, S.E.; Piel, J.; Medema, M.H.
Evolution of combinatorial diversity in trans-acyltransferase polyketide synthase assembly lines across bacteria
Nat. Commun.
12
1422
2021
Gynuella sunshinyii, Bacteria, Pseudomonas syringae
brenda
EXTERNAL LINKS (specific for EC-Number 2.3.1.206)
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