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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The expected taxonomic range for this enzyme is: Matricaria chamomilla

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EC NUMBER
COMMENTARY hide
4.2.3.136
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RECOMMENDED NAME
GeneOntology No.
alpha-isocomene synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = (-)-alpha-isocomene + diphosphate
show the reaction diagram
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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.
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
var. recutita
UniProt
Manually annotated by BRENDA team
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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
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-
?
(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
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?
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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only weakly expressed
Manually annotated by BRENDA team
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mainly expressed in roots
Manually annotated by BRENDA team
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only weakly expressed
Manually annotated by BRENDA team
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Y512F
mutant produces (E)-beta-caryophyllene and alpha-humulene, not isocomene
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LINKS TO OTHER DATABASES (specific for EC-Number 4.2.3.136)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)