Information on EC 4.2.3.133 - alpha-copaene synthase

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The expected taxonomic range for this enzyme is: Gunneridae

EC NUMBER
COMMENTARY hide
4.2.3.133
-
RECOMMENDED NAME
GeneOntology No.
alpha-copaene synthase
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = (-)-alpha-copaene + diphosphate
show the reaction diagram
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-
-
-
SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, alpha-copaene-forming)
Isolated from Helianthus annuus (sunflower). The enzyme also produces beta-caryophyllene, delta-cadinene and traces of other sesquiterpenoids. See EC 4.2.3.13 (+)-delta-cadinene synthase, EC 4.2.3.57 (-)-beta-caryophyllene synthase.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
isoform TPS2; cultivar HA300
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
; cultivar Desiree
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
-
tuber-specific over-expression of potato alpha-copaene synthase gene results in up to 15fold enhanced levels of alpha-copaene with a positive correlation between transgene expression level and alpha-copaene abundance. No aroma differences in the transgenic samples compared with controls and no significant differences in taste attributes are found. Sensory analysis suggests that alpha-copaene is not a major component of potato flavour
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
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
yield of 40% (+)-delta-cadinene
-
?
(2E,6E)-farnesyl diphosphate
(-)-alpha-copaene + diphosphate
show the reaction diagram
(2E,6E)-farnesyl diphosphate
alpha-copaene + diphosphate
show the reaction diagram
-
delta-cadinene is one of the two main products, while alpha-muuorlene, beta-caryophyllene, alpha-humulene and alpha-copaene are minor products
-
?
2 (2E,6E)-farnesyl diphosphate
alpha-copaene + delta-cadinene + 2 diphosphate
show the reaction diagram
-
bifunctional sesquiterpene synthase producing both alpha-copaene and delta-cadinene
-
?
geranylgeranyl diphosphate + H2O
(13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate
show the reaction diagram
it is proposed that a basic amino acid residue of the enzyme abstracts a proton from a molecule of water as the hydroxyl adds to the double bond at carbon7 of geranylgeranyl diphosphate. Concerted cyclization occurs and the double bond at carbon14 of geranylgeranyl diphosphate (carbon-3 of (8R)-hydroxy-copalyl diphosphate) is protonated. This concerted mechanism accounts for the addition of a single atom of 18O and a single atom of deuterium to geranylgeranyl diphosphate to form (8R)-hydroxy-copalyl diphosphate
first step in synthesis of sclareol
-
?
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0048
(2E,6E)-farnesyl diphosphate
pH 7.5, 30°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.04
(2E,6E)-farnesyl diphosphate
Phyla dulcis
J7LP58
pH 7.5, 30°C
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Ni-NTA affinity column chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Saccharomyces cerevisiae strain EPY300 as a thioredoxin-fusion protein
expressed in Saccharomyces cerevisiae strain EPY300; exprsssion in Escherichia coli and Saccharomyces cerevisiae
expression in Saccharomyces cerevisiae and Escherichia coli
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
nutrition
-
tuber-specific over-expression of potato alpha-copaene synthase gene results in up to 15fold enhanced levels of alpha-copaene with a positive correlation between transgene expression level and alpha-copaene abundance. No aroma differences in the transgenic samples compared with controls and no significant differences in taste attributes are found. Sensory analysis suggests that alpha-copaene is not a major component of potato flavour
synthesis
expression in Saccharomyces cerevisiae leads to a titer of (-)-alpha-copaene of 9 mg/l at 48 h and around 7 mg/l in Escherichia coli, and the titer of (+)-delta-cadinene is 6 mg/l in Saccharomyces cerevisiae and 3.5 mg/l in Escherichia coli