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
Synonyms
GUR
ECTree
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Substrates Products
Substrates Products on EC 4.2.3.72 - alpha-gurjunene synthase
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REACTION DIAGRAM
(2E,6E)-farnesyl diphosphate
(-)-alpha-gurjunene + diphosphate
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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
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(2E,6E)-farnesyl diphosphate
alpha-gurjunene + diphosphate
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additional information
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no activity with geranyl diphosphate and geranylgeranyl diphosphate
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