Information on EC 4.2.3.113 - terpinolene synthase

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The expected taxonomic range for this enzyme is: Spermatophyta

EC NUMBER
COMMENTARY
4.2.3.113
-
RECOMMENDED NAME
GeneOntology No.
terpinolene synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
geranyl diphosphate = terpinolene + diphosphate
show the reaction diagram
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-
-
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PATHWAY
KEGG Link
MetaCyc Link
monoterpene biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase (cyclizing, terpinolene-forming)
Requires Mg2+. Mn2+ is less effective and product ratio changes. Forms traces of other monoterpenoids.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
(+)-pinene cyclase
-
-
(-)-pinene cyclase
-
-
ag9
-
-
-
-
ag9
Q9M7D0
-
JF67
Q84SM8
-
JF67
Picea abies Karst.
Q84SM8
-
-
LaLIMS_RR
-
-
-
-
limonene synthase
Q2XSC6
-
PmeTPS2
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
250376-08-0
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ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(3R)-linalyl diphosphate
terpinolene + diphosphate
show the reaction diagram
-
-
products are 17% (-)-alpha-pinene, 9% beta-pinene, 3% camphene, 28% limonene, 9% terpinolene, 23% myrcene, 3% cis-ocimene, 13% trans-ocimene, products are 62% (+)-alpha-pinene, 6% camphene, 11% limonene, 7% terpinolene, 10% myrcene, 1% cis-ocimene, 4% trans-ocimene
-
?
(3S)-linalyl diphosphate
terpinolene + diphosphate
show the reaction diagram
-
-
products are 15% (-)-alpha-pinene, 18% beta-pinene, 12% camphene, 11% limonene, 6% terpinolene, 23% myrcene, 3% cis-ocimene, 8% trans-ocimene, products are 9% (+)-alpha-pinene, 9% camphene, 34% limonene, 28%% terpinolene, 11% myrcene, 2% cis-ocimene, 6% trans-ocimene
-
?
geranyl diphoshate
terpinolene + diphosphate
show the reaction diagram
Q9M7D0
-
42% terpinolene, 18% (-)-alpha-pinene, 11% (-)-limonene, 10% (-)-beta-pinene plus several minor products
-
?
geranyl diphosphate
terpinolene + diphosphate
show the reaction diagram
Q84SM8
-
78% (+)-car-3-ene plus 11% terpinolene plus minor products
-
?
geranyl diphosphate
terpinolene + diphosphate
show the reaction diagram
Q4QSN6
-
main product terpinolene, plus minor products (+)-alpha-pinene, gamma-terpinene, alpha-terpinene, (-)-limonene, sabinene, (-)-beta-pinene, and 3-carene
-
?
geranyl diphosphate
terpinolene + diphosphate
show the reaction diagram
-
-
products are 28% (-)-alpha-pinene, 35% beta-pinene, 24% camphene, 5% limonene, 2% terpinolene, 6% myrcene, products are 49% (+)-alpha-pinene, 30% camphene, 10% limonene, 5% terpinolene, 6% myrcene
-
?
neryl diphosphate
terpinolene + diphosphate
show the reaction diagram
-
-
products are 14% (+)-alpha-pinene, 9% camphene, 62% limonene, 8% terpinolene, 6% myrcene, products are 18% (-)-alpha-pinene, 18% beta-pinene, 12% camphene, 42% limonene, 9% terpinolene, 9% myrcene
-
?
geranyl diphosphate
terpinolene
show the reaction diagram
Q2XSC6
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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% a-phellandrene, when Mn2+ is supplied instead of Mg2+
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?
additional information
?
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Q9M7D0
entire product set is derived in stereochemically consistent fashion via (-)-3S-linalyl diphosphate as intermediate
-
-
-
additional information
?
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Q84SM8
no oxygenated or phosphorylated monoterpenes are found in detectable amounts
-
-
-
additional information
?
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Q4QSN6
no substrates: farnesyl diphosphate, geranygeranyl diphosphate
-
-
-
additional information
?
-
Q2XSC6
no substrates: farnesyl diphosphate, geranylgeranyl diphosphate
-
-
-
additional information
?
-
-
reaction follows a cisoid, anti-endo-pattern. In the case of geranyl diphosphate, a preassociation mechanism is suggested in which optimum folding of the terpenyl chain precedes the initial ionization step. The alternate substratse are ionized by the cyclases prior to their achieving the optimum orientation for bicyclization
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METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Mg2+
Q2XSC6
or Mn2+, reuired. Optimum concentraion 50 mM
Mn2+
Q2XSC6
or Mg2+, required. Optimum concentration 0.2 mM, 68% of the efficieny with Mg2+. 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+
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0035
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(3R)-linalyl diphosphate
-
pH 6.5, 30C
0.004
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(3R)-linalyl diphosphate
-
pH 6.5, 30C
0.0035
-
(3S)-linalyl diphosphate
-
pH 6.5, 30C
0.0049
-
(3S)-linalyl diphosphate
-
pH 6.5, 30C
0.0021
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geranyl diphosphate
-
pH 6.5, 30C
0.003
-
geranyl diphosphate
-
pH 6.5, 30C
0.0474
-
geranyl diphosphate
Q2XSC6
pH 7.0, 30C
0.0021
-
neryl diphosphate
-
pH 6.5, 30C
0.006
-
neryl diphosphate
-
pH 6.5, 30C
kcat/KM VALUE [1/mMs-1]
kcat/KM VALUE [1/mMs-1] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.255
-
geranyl diphosphate
Q2XSC6
pH 7.0, 30C
10850
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
pI VALUE
pI VALUE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6.2
-
Q84SM8
calculated
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
Q2XSC6
x * 70300, SDS-PAGE
?
Q84SM8
x * 71912, calculated
?
Picea abies Karst.
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x * 71912, calculated
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POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
proteolytic modification
Q9M7D0
sequence contains a putative plastid targeting signal
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expression in Escherichia coli
Q9M7D0
expression in Escherichia coli
Q2XSC6
expression in Escherichia coli
Q84SM8
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
treatment with methyl jasmonate induces transient transcript accumulation in stem tissues
Q84SM8
treatment with methyl jasmonate induces transient transcript accumulation in stem tissues
Picea abies Karst.
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