Information on EC 4.2.3.136 - alpha-isocomene synthase

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The expected taxonomic range for this enzyme is: Matricaria chamomilla

EC NUMBER
COMMENTARY hide
4.2.3.136
-
RECOMMENDED NAME
GeneOntology No.
alpha-isocomene synthase
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = (-)-alpha-isocomene + diphosphate
show the reaction diagram
SYSTEMATIC NAME
IUBMB Comments
(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.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
var. recutita
UniProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
(-)-alpha-isocomene + diphosphate
show the reaction diagram
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
-
-
?
(2E,6E)-farnesyl diphosphate
alpha-isocomene + diphosphate
show the reaction diagram
-
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
-
-
?
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
only weakly expressed
Manually annotated by BRENDA team
-
mainly expressed in roots
Manually annotated by BRENDA team
-
only weakly expressed
Manually annotated by BRENDA team
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Y512F
mutant produces (E)-beta-caryophyllene and alpha-humulene, not isocomene