Literature summary for 4.2.3.136 extracted from

Hong, Y.J.; Irmisch, S.; Wang, S.C.; Garms, S.; Gershenzon, J.; Zu, L.; Koellner, T.G.; Tantillo, D.J.
Theoretical and experimental analysis of the reaction mechanism of MrTPS2, a triquinane-forming sesquiterpene synthase from chamomile (2013), Chemistry, 19, 13590-13600.

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Protein Variants

Protein Variants	Comment	Organism
Y512F	mutant produces (E)-beta-caryophyllene and alpha-humulene, not isocomene	Matricaria chamomilla

Organism

Organism	UniProt	Comment	Textmining
Matricaria chamomilla	I6R4V5	var. recutita	-

Reaction

Reaction	Comment	Organism	Reaction ID
(2E,6E)-farnesyl diphosphate = (-)-alpha-isocomene + diphosphate	reaction proceeds through caryophyllyl and presilphiperfolanyl cations and involves the protonation of a stable (-)-(E)-beta-caryophyllene intermediate	Matricaria chamomilla	a

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
(2E,6E)-farnesyl diphosphate	reaction mechanism most likely involves repeated cycles of protonation/deprotonation of a neutral (-)-(E)-beta-caryophyllene intermediate. The deprotonation of the final isocomyl carbocation can occur either at C1 or C13, resulting in the main product alpha-isocomene and the minor product beta-isocomene	Matricaria chamomilla	(-)-alpha-isocomene + diphosphate	-	?

Synonyms

Synonyms	Comment	Organism
TPS2	-	Matricaria chamomilla

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Release 2023.1 (January 2023)