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Information on EC 4.2.3.107 - (+)-car-3-ene synthase and Organism(s) Picea sitchensis and UniProt Accession F1CKI9
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EC Tree
4.2.3.107 (+)-car-3-ene synthaseIUBMB Comments
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 .
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Word Map
The taxonomic range for the selected organisms is: Picea sitchensis
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Synonyms
(+)-3-carene synthase, 3-carene synthase, li3cars, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(+)-3-carene synthase
3-carene cyclase
-
-
-
-
3-carene synthase
-
-
-
-
3CAR
-
-
-
-
(+)-3-carene synthase
-
-
-
-
PATHWAY SOURCE
PATHWAYS
-
-, -
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
153190-33-1
-
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate
(+)-car-3-ene + diphosphate
-
major product, plus some terpinolene
-
?
geranyl diphosphate
(+)-car-3-ene + diphosphate
-
wild-type produces 46.2% (+)-car-3-ene, 8.8% (-)-sabinene, 29.7% terpinolene
-
?
geranyl diphosphate
(+)-car-3-ene + diphosphate
-
major product, plus some terpinolene
-
?
geranyl diphosphate
(+)-car-3-ene + diphosphate
-
wild-type produces 49% (+)-car-3-ene, 8.7% (-)-sabinene, 24.7% terpinolene
-
?
geranyl diphosphate
(+)-car-3-ene + diphosphate
-
wild-type produces 67.5% (+)-car-3-ene, 6.9% (-)-sabinene, 15.4% terpinolene
-
?
additional information
?
-
poor substrate: neryl diphosphate. No substrates: farnesyl diphosphate, geranylgeranyl diphosphate
-
-
?
additional information
?
-
poor substrate: neryl diphosphate. No substrates: farnesyl diphosphate, geranylgeranyl diphosphate
-
-
?
additional information
?
-
poor substrate: neryl diphosphate. No substrates: farnesyl diphosphate, geranylgeranyl diphosphate
-
-
?
additional information
?
-
-
poor substrate: neryl diphosphate. No substrates: farnesyl diphosphate, geranylgeranyl diphosphate
-
-
?
additional information
?
-
poor substrate: neryl diphosphate. No substrates: farnesyl diphosphate, geranylgeranyl diphosphate
-
-
?
additional information
?
-
poor substrate: neryl diphosphate. No substrates: farnesyl diphosphate, geranylgeranyl diphosphate
-
-
?
additional information
?
-
poor substrate: neryl diphosphate. No substrates: farnesyl diphosphate, geranylgeranyl diphosphate
-
-
?
additional information
?
-
-
poor substrate: neryl diphosphate. No substrates: farnesyl diphosphate, geranylgeranyl diphosphate
-
-
?
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
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
LITERATURE
IMAGE
0.00688
geranyl diphosphate
pH 7.4, 30°C, proteins from both susceptible and resistant plants have similar kinetic parameters
0.0153
geranyl diphosphate
mutant L596F, 30°C, pH not specified in the publication
0.0158
geranyl diphosphate
wild-type, 30°C, pH not specified in the publication
additional information
additional information
isoform 3car3 has an extremely low activity
-
additional information
additional information
isoform 3car3 has an extremely low activity
-
additional information
additional information
isoform 3car3 has an extremely low activity
-
additional information
additional information
-
isoform 3car3 has an extremely low activity
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.098
geranyl diphosphate
wild-type, 30°C, pH not specified in the publication
0.643
geranyl diphosphate
mutant L596F, 30°C, pH not specified in the publication
2.21
geranyl diphosphate
pH 7.4, 30°C, proteins from both susceptible and resistant plants have similar kinetic parameters
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0062
geranyl diphosphate
wild-type, 30°C, pH not specified in the publication
0.042
geranyl diphosphate
mutant L596F, 30°C, pH not specified in the publication
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
isoform TPS-3car3, only expressed in trees susceptilble to white pine weevil
UniProt
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
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
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
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). 3CAR3_PICSI
627
0
71661
Swiss-Prot
Chloroplast (Reliability: 2)
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
G595A/L596F/F599L
shift in product profile, mutant produces 5.4% (+)-car-3-ene, 29.0% (-)-sabinene, 26.4% terpinolene
L596F
shift in product profile, mutant produces 9.2% (+)-car-3-ene, 20.2% (-)-sabinene, 32.2% terpinolene
G595A/L596F/F599L
L596F
additional information
G595A/L596F/F599L
shift in product profile, mutant produces 1.8% (+)-car-3-ene, 23.3% (-)-sabinene, 55.2% terpinolene
G595A/L596F/F599L
shift in product profile, mutant produces 4.7% (+)-car-3-ene, 47.4% (-)-sabinene, 35.2% terpinolene
L596F
shift in product profile, mutant produces 12.3% (+)-car-3-ene, 37.4% (-)-sabinene, 35.4% terpinolene
L596F
shift in product profile, mutant produces 5% (+)-car-3-ene, 20.9% (-)-sabinene, 53.5% terpinolene
additional information
construction of a series of domain swaps and site-directed substitutions between (-)-sabinene synthase and (+)-3-carene synthase isoforms to explore which regions and specific amino acids of these enzymes affect the differences of their product profiles. The amino acid in position 596 is critical for product profiles dominated by (+)-3-carene in (+)-3-carene synthase isoforms. A leucine in this position promotes formation of (+)-3-carene, whereas phenylalanine promotes (-)-sabinene
additional information
construction of a series of domain swaps and site-directed substitutions between (-)-sabinene synthase and (+)-3-carene synthase isoforms to explore which regions and specific amino acids of these enzymes affect the differences of their product profiles. The amino acid in position 596 is critical for product profiles dominated by (+)-3-carene in (+)-3-carene synthase isoforms. A leucine in this position promotes formation of (+)-3-carene, whereas phenylalanine promotes (-)-sabinene
additional information
construction of a series of domain swaps and site-directed substitutions between (-)-sabinene synthase and (+)-3-carene synthase isoforms to explore which regions and specific amino acids of these enzymes affect the differences of their product profiles. The amino acid in position 596 is critical for product profiles dominated by (+)-3-carene in (+)-3-carene synthase isoforms. A leucine in this position promotes formation of (+)-3-carene, whereas phenylalanine promotes (-)-sabinene
additional information
-
construction of a series of domain swaps and site-directed substitutions between (-)-sabinene synthase and (+)-3-carene synthase isoforms to explore which regions and specific amino acids of these enzymes affect the differences of their product profiles. The amino acid in position 596 is critical for product profiles dominated by (+)-3-carene in (+)-3-carene synthase isoforms. A leucine in this position promotes formation of (+)-3-carene, whereas phenylalanine promotes (-)-sabinene
additional information
construction of a series of domain swaps and site-directed substitutions between (-)-sabinene synthase and (+)-3-carene synthase isoforms to explore which regions and specific amino acids of these enzymes affect the differences of their product profiles. The amino acid in position 596 is critical for product profiles dominated by (+)-3-carene in (+)-3-carene synthase isoforms. A leucine in this position promotes formation of (+)-3-carene, whereas phenylalanine promotes (-)-sabinene
additional information
construction of a series of domain swaps and site-directed substitutions between (-)-sabinene synthase and (+)-3-carene synthase isoforms to explore which regions and specific amino acids of these enzymes affect the differences of their product profiles. The amino acid in position 596 is critical for product profiles dominated by (+)-3-carene in (+)-3-carene synthase isoforms. A leucine in this position promotes formation of (+)-3-carene, whereas phenylalanine promotes (-)-sabinene
additional information
construction of a series of domain swaps and site-directed substitutions between (-)-sabinene synthase and (+)-3-carene synthase isoforms to explore which regions and specific amino acids of these enzymes affect the differences of their product profiles. The amino acid in position 596 is critical for product profiles dominated by (+)-3-carene in (+)-3-carene synthase isoforms. A leucine in this position promotes formation of (+)-3-carene, whereas phenylalanine promotes (-)-sabinene
additional information
-
construction of a series of domain swaps and site-directed substitutions between (-)-sabinene synthase and (+)-3-carene synthase isoforms to explore which regions and specific amino acids of these enzymes affect the differences of their product profiles. The amino acid in position 596 is critical for product profiles dominated by (+)-3-carene in (+)-3-carene synthase isoforms. A leucine in this position promotes formation of (+)-3-carene, whereas phenylalanine promotes (-)-sabinene
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hall, D.E.; Robert, J.A.; Keeling, C.I.; Domanski, D.; Quesada, A.L.; Jancsik, S.; Kuzyk, M.A.; Hamberger, B.; Borchers, C.H.; Bohlmann, J.
An integrated genomic, proteomic and biochemical analysis of (+)-3-carene biosynthesis in Sitka spruce (Picea sitchensis) genotypes that are resistant or susceptible to white pine weevil
Plant J.
65
936-948
2011
Picea sitchensis (F1CKI6), Picea sitchensis (F1CKI8), Picea sitchensis (F1CKI9), Picea sitchensis
Roach, C.R.; Hall, D.E.; Zerbe, P.; Bohlmann, J.
Plasticity and evolution of (+)-3-carene synthase and (-)-sabinene synthase functions of a Sitka spruce monoterpene synthase gene family associated with weevil resistance
J. Biol. Chem.
289
23859-23869
2014
Picea sitchensis (F1CKI6), Picea sitchensis (F1CKI8), Picea sitchensis (F1CKI9), Picea sitchensis
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