Information on EC 4.2.3.20 - (R)-limonene synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
4.2.3.20
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RECOMMENDED NAME
GeneOntology No.
(R)-limonene synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate = (R)-limonene + diphosphate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
cyclization
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
(4S)-carvone biosynthesis
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Biosynthesis of secondary metabolites
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Metabolic pathways
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Monoterpenoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-(4R)-limonene-forming]
Forms the first step of carvone biosynthesis in caraway. The enzyme from Carum carvi (caraway) seeds requires a divalent metal ion (preferably Mn2+) for catalysis. This enzyme occurs in Citrus, Carum (caraway) and Anethum (dill); (-)-limonene, however, is made in the fir, Abies, and mint, Mentha, by EC 4.2.3.16, (4S)-limonene synthase.
CAS REGISTRY NUMBER
COMMENTARY hide
155807-65-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
Marc.
-
-
Manually annotated by BRENDA team
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-
-
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
geranyl diphosphate
(+)-(4R)-limonene + diphosphate
show the reaction diagram
-
-
-
?
geranyl diphosphate
(+)-(R)-limonene + diphosphate
show the reaction diagram
geranyl diphosphate
(1R,4S)-(+)-camphene + diphosphate
show the reaction diagram
-
-
-
-
geranyl diphosphate
(1R,5R)-(+)-alpha-pinene + diphosphate
show the reaction diagram
-
-
-
-
geranyl diphosphate
(4R)-limonene + diphosphate
show the reaction diagram
geranyl diphosphate
(R)-limonene
show the reaction diagram
-
products are 39% (R)-limonene, 22% terpinolene, 16% (1R,5S)-camphene, 14% (1R,5R)-(+)-alpha-pinene, 8% betamyrcene and traces of alpha-phellandrene. Product pattern changes markedly to 46% limonene, 9% terpinolene, 23% alpha-pinene, 5% beta-myrcene and 4% alpha-phellandrene, when Mn2+ is supplied instead of Mg2+
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?
geranyl diphosphate
alpha-phellandrene + diphosphate
show the reaction diagram
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-
-
-
geranyl diphosphate
beta-myrcene + diphosphate
show the reaction diagram
-
-
-
-
geranyl diphosphate
D-limonene + diphosphate
show the reaction diagram
single step in plants
D-limonene shows cancer preventative and cancer therapeutic activities in vitro and in vivo, its modulates apoptosis-related genes and proteins in cultured cells
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?
geranyl diphosphate
terpinolene + diphosphate
show the reaction diagram
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-
-
-
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate
(+)-(4R)-limonene + diphosphate
show the reaction diagram
Q2XSC6
-
-
-
?
geranyl diphosphate
(+)-(R)-limonene + diphosphate
show the reaction diagram
geranyl diphosphate
D-limonene + diphosphate
show the reaction diagram
Q9FUW5
single step in plants
D-limonene shows cancer preventative and cancer therapeutic activities in vitro and in vivo, its modulates apoptosis-related genes and proteins in cultured cells
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?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
geranyl diphosphate
substrate inhibition above 0.01 mM; substrate inhibition above 0.01 mM
K+
maximum inhibition above 100 mM; maximum inhibition above 100 mM
Mn2+
above 0.6 mM, activation below; above 0.6 mM, activation below
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Mn2+
inhibition above 0.6 mM, activation below; inhibition above 0.6 mM, activation below
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0007 - 0.0474
geranyl diphosphate
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.012
geranyl diphosphate
Lavandula angustifolia
Q2XSC6
LaLIMS_RR, truncated protein
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.255
geranyl diphosphate
Lavandula angustifolia
Q2XSC6
pH 7.0, 30°C
175
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
23
standard activity assay
30
; optimized assay, LaLIMS_RR, truncated protein
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
peel of young developing fruit
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
-
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Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60000
x * 60000, SDS-PAGE
62000
x * 62000, SDS-PAGE, x * 64000, deduced from gene sequence
64000
x * 62000, SDS-PAGE, x * 64000, deduced from gene sequence
70000
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1 * 70000, recombinant GST fusion protein, SDS-PAGE
70300
x * 70300, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
using GST bind resin
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in NIH 3T3 cell; The cDNA of D-limonene synthase obtained from Japanese catnip, modified by deletion of the transit peptide sequence and addition of a new ATG initiation codon, is cloned. Establishment of transgenic mouse embryonic NIH 3T3 fibroblast cells that produce limonene by introducing the D-limonene synthase gene. Apoptosis is not observed in the limonene-producing cells.
expression in Escherichia coli; into the pGEM-T vector for sequencing and into the pGEX-T-1 vector for expression in Escherichia coli cells
functional expression of four cDNA clones in Escherichia coli
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introduction of limonene synthase cDNA with three different sorting signals (to localize either in cytosol or the endoplasmic reticulum) in Nicotiana tabacum. Full-length and modified enzyme are subcloned in a binary vector under the El2 promoter, which is a strong constitutive promoter, to yield pBin-FullLC1, pBin-DEltaLC1 and pBin.ERLC1 to plastidial, cytosolic and endoplasmic localization, respectively. These plasmids are introduced via Agrobacterium tumefaciens into tobacco. More than 10 transgenic tobacco plants for each construct, i.e. 15 plastid localization, 17 cytosol localization, 11 endoplasmic reticulum localization are established
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limonene cyclase enzyme Cl(+)LIMS2 produced exclusively (+)-limonene as the major product of the enzymatic catalysis. In a chimeric enzyme, substitution of ClgammaTS domain III and domain IV by their counterparts from Cl(+)LIMS2 changed product specificity to that of Cl(+)LIMS2, (+)-limonene being the major product formed
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
D-limonene is effective in cancer prevention in animal cancer models, some clinical applications have been performed