Literature summary for 4.2.3.24 extracted from

Picaud, S.; Mercke, P.; He, X.; Sterner, O.; Brodelius, M.; Cane, D.E.; Brodelius, P.E.
Amorpha-4,11-diene synthase: mechanism and stereochemistry of the enzymatic cyclization of farnesyl diphosphate (2006), Arch. Biochem. Biophys., 448, 150-155.

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Organism

Organism	UniProt	Comment	Textmining
Artemisia annua	-	expression in Escherichia coli	-

Reaction

Reaction	Comment	Organism	Reaction ID
(2E,6E)-farnesyl diphosphate = amorpha-4,11-diene + diphosphate	mechanism involves isomerzation of farnesyl diphosphate to (R)-nerolidyl diphosphate, ionization, and C-1,C-6-ring closure to generate a bisabolyl cation, followed by a 1,3-hydride shift, 1,10-ring closure, and deprotonation at either C-12 or C-13	Artemisia annua	a

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
farnesyl diphosphate	-	Artemisia annua	amorpha-4,7-diene + diphosphate	configuration is 1S,6R,7R,10R-amorpha-4,11-diene	?
additional information	H-1si-proton of substrate is transferred during the cyclization reaction to carbon 10 of amorphadiene, as a result of a 1,3-hydride-shift follwing initial 1,6 ring closure, while the H-1re-proton of substrate is retained on C-6 of the product	Artemisia annua	?	-	?

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Release 2023.1 (January 2023)