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Information on EC 4.2.3.136 - alpha-isocomene synthase for references in articles please use BRENDA:EC4.2.3.136Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
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The expected taxonomic range for this enzyme is: Matricaria chamomilla
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alpha-isocomene synthase
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(2E,6E)-farnesyl diphosphate = (-)-alpha-isocomene + diphosphate
(2E,6E)-farnesyl diphosphate = (-)-alpha-isocomene + diphosphate
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(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
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(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, (-)-alpha-isocomene-forming)
Isolated from the roots of the plant Matricaria chamomilla var. recutita (chamomile). The enzyme also produced traces of five other sesquiterpenoids.
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MrTPS2
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var. recutita
UniProt
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brenda
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(2E,6E)-farnesyl diphosphate
(-)-alpha-isocomene + 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
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(2E,6E)-farnesyl diphosphate
alpha-isocomene + diphosphate
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MrTPS2 shows a broader sesquiterpene product spectrum with the angular triquinane, alpha-isocomene, being the main compound. The enzyme produces detectable amounts of three other triquinanes, beta-isocomene, silphinene and modeph-2-ene. Like MrTPS1 it also produces (E)-beta-caryophyllene and alpha-humulene, but in low amounts
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only weakly expressed
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mainly expressed in roots
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only weakly expressed
brenda
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Y512F
mutant produces (E)-beta-caryophyllene and alpha-humulene, not isocomene
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TPS2_MATCR
546
63446
Swiss-Prot
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Irmisch, S.; Krause, S.T.; Kunert, G.; Gershenzon, J.; Degenhardt, J.; Koellner, T.G.
The organ-specific expression of terpene synthase genes contributes to the terpene hydrocarbon composition of chamomile essential oils
BMC Plant Biol.
12
84
2012
Matricaria chamomilla var. recutita
brenda
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
Chemistry
19
13590-13600
2013
Matricaria chamomilla (I6R4V5)
brenda
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