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4.2.3.133: alpha-copaene synthase

This is an abbreviated version!
For detailed information about alpha-copaene synthase, go to the full flat file.

Reaction

(2E,6E)-farnesyl diphosphate
=
(-)-alpha-copaene
+
diphosphate

Synonyms

(Z)-beta-cubebene/alpha-copaene synthase, alpha-copaene synthase, bifunctional sesquiterpene synthase 1, CsSesquiTPS1, SES1, sesquiterpene synthase, sesquiterpene synthase 1, SeTPS1, TPS04, TPS1, TPS2

ECTree

     4 Lyases
         4.2 Carbon-oxygen lyases
             4.2.3 Acting on phosphates
                4.2.3.133 alpha-copaene synthase

Substrates Products

Substrates Products on EC 4.2.3.133 - alpha-copaene synthase

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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
-
-
-
-
?
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
J9PDV7
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
-
?