Information on EC 4.2.3.107 - (+)-car-3-ene synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
4.2.3.107
-
RECOMMENDED NAME
GeneOntology No.
(+)-car-3-ene synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate = (+)-car-3-ene + diphosphate
show the reaction diagram
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
3-carene biosynthesis
-
-
oleoresin monoterpene volatiles biosynthesis
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-
SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-car-3-ene-forming]
The enzyme reacts with (3S)-linalyl diphosphate twice as rapidly as geranyl diphosphate, but 25 times as rapidly as (3R)-linalyl diphosphate. It is assumed that (3S)-linalyl diphosphate is normally formed as an enzyme bound intermediate in the reaction. In the reaction the 5-pro-R hydrogen of geranyl diphosphate is eliminated during cyclopropane ring formation [1,2]. In Picea abies (Norway spruce) and Picea sitchensis (Sitka spruce) terpinolene is also formed [4,6]. See EC 4.2.3.113 terpinolene synthase. (+)-Car-3-ene is associated with resistance of Picea sitchensis (Sitka spruce) to white pine weevil [6].
CAS REGISTRY NUMBER
COMMENTARY hide
153190-33-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
(+)-3-carene is associated with resistance of Sitka spruce to white pine weevil, Pissodes strobi. Variation of the (+)-3-carene phenotype is controlled by copy number variation of TPS-3car genes, variation of gene and protein expression, and variation in catalytic efficiencies; (+)-3-carene is associated with resistance of Sitka spruce to white pine weevil, Pissodes strobi. Variation of the (+)-3-carene phenotype is controlled by copy number variation of TPS-3car genes, variation of gene and protein expression, and variation in catalytic efficiencies; (+)-3-carene is associated with resistance of Sitka spruce to white pine weevil, Pissodes strobi. Variation of the (+)-3-carene phenotype is controlled by copy number variation of TPS-3car genes, variation of gene and protein expression, and variation in catalytic efficiencies
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(3R)-linalyl diphosphate
? + diphosphate
show the reaction diagram
-
-
the velocity of the reaction with the (3S)-linalyl enantiomer is 25fold greater than the velocity with the (3R)-enantiomer and twice that of the natural substrate, geranyl diphosphate. Cyclization of the linalyl intermediate is faster than the coupled isomerization and cyclization of the geranyl substrate
-
?
(3R)-linalyl diphosphate
myrcene + diphosphate
show the reaction diagram
-
-
-
-
?
(3S)-linalyl diphosphate
(+)-car-3-ene + diphosphate
show the reaction diagram
-
-
more than 99.9% optically pure
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?
(3S)-linalyl diphosphate
? + diphosphate
show the reaction diagram
-
-
the velocity of the reaction with the (3S)-linalyl enantiomer is 25fold greater than the velocity with the (3R)-enantiomer and twice that of the natural substrate, geranyl diphosphate. Cyclization of the linalyl intermediate is faster than the coupled isomerization and cyclization of the geranyl substrate
-
?
geranyl diphosphate
(+)-car-3-ene
show the reaction diagram
-
major product, plus some terpinolene
-
?
geranyl diphosphate
(+)-car-3-ene + diphosphate
show the reaction diagram
additional information
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Cs+
-
about 50% of the activation by K+
Fe2+
-
or Mn2+, required
K+
-
and Rb+, best activation
Mn2+
-
or Fe2+, required
NH4+
-
about 80% of the activation by K+
Rb+
-
and K+, activation
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
diethyl dicarbonate
-
formation of a substrate-metal ion complex does not protect against inhibition
N-ethylmaleimide
-
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Phenylglyoxal
-
inactivation
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
methyl jasmonate
protein is detected at significantly higher levels in susceptible trees compared to resistant trees at day 7 after methyl jasmonate treatment
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0017 - 0.0047
(3R)-linalyl diphosphate
0.0015 - 0.0028
(3S)-linalyl diphosphate
0.0037 - 0.0158
geranyl diphosphate
additional information
additional information
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.098 - 2.21
geranyl diphosphate
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0062 - 0.042
geranyl diphosphate
175
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.05
N-ethylmaleimide
Pinus contorta
-
pH 6.5, 31°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.2
calculated
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
29% of xylem activity
Manually annotated by BRENDA team
-
22% of xylem activity
Manually annotated by BRENDA team
peltate glandular trichome
Manually annotated by BRENDA team
-
highest enzymic activity
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
69700
x * 69700, calculated for preprotein
71912
x * 71912, calculated
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
proteolytic modification
sequence contains a N-terminal transit peptide
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
transcript levels are increased following methyl jasmonate treatment, with transcripts detected at significantly higher abundance in resistant trees compared to susceptible trees
treatment with methyl jasmonate induces transient transcript accumulation in stem tissues
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
G595A/L596F/F599L
shift in product profile, mutant produces 1.8% (+)-car-3-ene, 23.3% (-)-sabinene, 55.2% terpinolene; shift in product profile, mutant produces 4.7% (+)-car-3-ene, 47.4% (-)-sabinene, 35.2% terpinolene; shift in product profile, mutant produces 5.4% (+)-car-3-ene, 29.0% (-)-sabinene, 26.4% terpinolene
L596F
shift in product profile, mutant produces 12.3% (+)-car-3-ene, 37.4% (-)-sabinene, 35.4% terpinolene; shift in product profile, mutant produces 5% (+)-car-3-ene, 20.9% (-)-sabinene, 53.5% terpinolene; shift in product profile, mutant produces 9.2% (+)-car-3-ene, 20.2% (-)-sabinene, 32.2% terpinolene
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
-
PCR-based approach to identify BAC clones for two target genes, 3-carene synthase and a cytochrome P450 from a non-arrayed genomic BAC library. Shotgun genomic fragments isolated from the BAC clones were sequenced to a depth of 15.6- and 16.0fold coverage, respectively. Assembly and manual curation yielded sequence scaffolds of 172 kbp long for 3CAR. Inspection of the genomic sequences reveals the intron-exon structures, the putative promoterregions and putative cis-regulatory elements. Sequences related to transposable elements, high complexity repeats and simple repeats are prevalent and comprise approximately 40% of the sequenced genomic DNA