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4.2.3.72: alpha-gurjunene synthase

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

Reaction

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

Synonyms

GUR

ECTree

     4 Lyases
         4.2 Carbon-oxygen lyases
             4.2.3 Acting on phosphates
                4.2.3.72 alpha-gurjunene synthase

Substrates Products

Substrates Products on EC 4.2.3.72 - alpha-gurjunene 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
(-)-alpha-gurjunene + diphosphate
show the reaction diagram
-
initial step is the formation of a germacrenyl cation after abstraction of the diphosphate group. Internal shifts of electron pairs lead to the patchoulenyl cation, which then undergoes a double 1,2-hydride shift. Rearrangement leads to the aromadendrenyl cation, which then undergoes a 1,2-hydride shift. Abstraction of a proton by the enzyme yields isoledene, which is reprotonated at the active site of the enzyme. At this junction two proton abstractions are possible, one leading to (-)-alpha-gurjunene and the other to (+)-gamma-gurjunene
product ratio 91% (-)-alpha-gurjunene and 9% (+)-gamma-gurjunene
-
?
(2E,6E)-farnesyl diphosphate
alpha-gurjunene + diphosphate
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
no activity with geranyl diphosphate and geranylgeranyl diphosphate
-
-
?