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Information on EC 4.2.3.136 - alpha-isocomene synthase for references in articles please use BRENDA:EC4.2.3.136
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EC Tree
IUBMB Comments Isolated from the roots of the plant Matricaria chamomilla var. recutita (chamomile). The enzyme also produced traces of five other sesquiterpenoids.
The expected taxonomic range for this enzyme is: Matricaria chamomilla
Synonyms
MrTPS2, TPS2,
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MrTPS2
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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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(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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var. recutita
UniProt
brenda
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brenda
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only weakly expressed
brenda
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mainly expressed in roots
brenda
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only weakly expressed
brenda
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TPS2_MATCR
546
0
63446
Swiss-Prot
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Y512F
mutant produces (E)-beta-caryophyllene and alpha-humulene, not isocomene
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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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4.2.3.136 alpha-isocomene synthase
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