Information on EC 2.3.1.206 - 3,5,7-trioxododecanoyl-CoA synthase

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The expected taxonomic range for this enzyme is: Cannabis sativa

EC NUMBER
COMMENTARY hide
2.3.1.206
-
RECOMMENDED NAME
GeneOntology No.
3,5,7-trioxododecanoyl-CoA synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
3 malonyl-CoA + hexanoyl-CoA = 3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
show the reaction diagram
-
-
-
-
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.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene pks
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
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
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3 malonyl-CoA + butyryl-CoA
?
show the reaction diagram
-
-
formation of resorcinol
-
?
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
show the reaction diagram
3 malonyl-CoA + hexanoyl-CoA
?
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
3 malonyl-CoA + hexanoyl-CoA
3 CoA + 3,5,7-trioxododecanoyl-CoA + 3 CO2
show the reaction diagram
additional information
?
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0861 - 0.0889
butyryl-CoA
-
pH 5.5, 30°C, dependent on product formed
0.0569 - 0.0631
Hexanoyl-CoA
-
pH 5.5, 30°C, dependent on product formed
additional information
additional information
-
no allosteric regulation of TKS
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.011 - 0.012
butyryl-CoA
Cannabis sativa
-
pH 5.5, 30°C, dependent on product formed
0.018 - 0.058
Hexanoyl-CoA
Cannabis sativa
-
pH 5.5, 30°C, dependent on product formed
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.129 - 0.134
butyryl-CoA
Cannabis sativa
-
pH 5.5, 30°C, dependent on product formed
270
0.28 - 1.013
Hexanoyl-CoA
Cannabis sativa
-
pH 5.5, 30°C, dependent on product formed
395
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0024
-
highest tissue activity, in bracts, pH 7.0, 30°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5
-
assay at
6.8
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assay at
7
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assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.04
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sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
very high levels of cannabinoids in the flower tops
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
42585
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2 * 42585, sequence calculation, 2 x 44000, recombinant C-terminally His-tagged enzyme, SDS-PAGE
42700
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x * 42700, about, sequence calculation, x * 45000, SDS-PAGE
45000
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x * 42700, about, sequence calculation, x * 45000, SDS-PAGE
89000
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recombinant C-terminally His-tagged enzyme, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
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2 * 42585, sequence calculation, 2 x 44000, recombinant C-terminally His-tagged enzyme, SDS-PAGE
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
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gene pks, cDNA and amino acid sequence determination and analysis, overexpression of His-tagged PKS in Escherichia coli strain M15
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recombinant expression of the C-terminally His-tagged enzyme
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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the goal for engineering of zero-cannabinoid plants is knocking out the first step of the biosynthesis catalyzed by the type III PKS enzyme