Information on EC 4.2.3.39 - epi-cedrol synthase

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The expected taxonomic range for this enzyme is: Artemisia annua

EC NUMBER
COMMENTARY hide
4.2.3.39
-
RECOMMENDED NAME
GeneOntology No.
epi-cedrol synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate + H2O = 8-epi-cedrol + diphosphate
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
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-
Sesquiterpenoid and triterpenoid biosynthesis
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-
SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (8-epi-cedrol-forming)
The enzyme is activated by Mg2+ [2]. Similar to many other plant terpenoid synthases, this enzyme produces many products from a single substrate. The predominant product is the cyclic sesquiterpenoid alcohol, 8-epi-cedrol, with minor products including cedrol and the olefins alpha-cedrene, beta-cedrene, (E)-beta-farnesene and (E)-alpha-bisabolene [1].
CAS REGISTRY NUMBER
COMMENTARY hide
251113-52-7
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate + H2O
8-epi-cedrol + diphosphate
show the reaction diagram
geranyl diphosphate + H2O
? + diphosphate
show the reaction diagram
geranyl diphosphate is converted to monoterpenes by the recombinant enzyme at a rate of about 15% of that observed with farnesyl diphosphate as substrate
-
-
?
additional information
?
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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
(2E,6E)-farnesyl diphosphate + H2O
8-epi-cedrol + diphosphate
show the reaction diagram
additional information
?
-
Q9LLR9
Sesquiterpene cyclases or synthases catalyze the conversion of the isoprenoid intermediate farnesyl diphosphate to various sesquiterpene structural types
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
-
activates at 2 mM
Mn2+
-
highly activating at 0.060 mM, inhibiting at 0.12 mM
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Mn2+
-
highly activating at 0.060 mM, inhibiting at 0.12 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0004 - 0.0013
(2E,6E)-farnesyl diphosphate
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.5 - 9
-
alcohol product formation
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.3 - 9
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-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
22
assay at room temperature
25
-
assay at
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.94
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sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
63500
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x * 63500, about, sequence calculation
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 63500, about, sequence calculation
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloning from a cDNA library, DNA and amino acid sequence determination and analysis, expression in Escherichia coli strain XL1-Blue
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functional expression in Saccharomyces cerevisiae, native mating type alpha yeast strain JBY574 and constructed strain EHY42, leading to production of sesquiterpenes in yeast. Expressing epi-cedrol synthase in the upc2-1 mutant CJ-2A actually decreases foreign sesquiterpene yields relative to wild-type strain. FPP is apparently less accessible to the epi-cedrol synthase in the upc2-1 mutant, overview. Mating type influences foreign sesquiterpene production, overview
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homology-based cloning from a cDNA library, DNA and amino acid sequence determination and analysis, cloning and expression in Escherichia coli strains DH5alpha and BL21(DE3), respectively