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 hide
4.2.3.113
-
RECOMMENDED NAME
GeneOntology No.
terpinolene synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate = terpinolene + diphosphate
show the reaction diagram
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-
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PATHWAY
BRENDA Link
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.
CAS REGISTRY NUMBER
COMMENTARY hide
250376-08-0
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
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UniProt
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
(3R)-linalyl diphosphate
terpinolene + diphosphate
show the reaction diagram
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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
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?
(3S)-linalyl diphosphate
terpinolene + diphosphate
show the reaction diagram
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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
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?
2 geranyl diphosphate
(+)-car-3-ene + terpinolene + 2 diphosphate
show the reaction diagram
2 geranyl diphosphate
(-)-sabinene + terpinolene + 2 diphosphate
show the reaction diagram
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wild-type produces 1.3% (+)-car-3-ene, 44.7% (-)-sabinene, 35.9% terpinolene
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?
geranyl diphosphate
terpinolene
show the reaction diagram
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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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?
geranyl diphosphate
terpinolene + diphosphate
show the reaction diagram
neryl diphosphate
terpinolene + diphosphate
show the reaction diagram
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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
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?
additional information
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
or Mn2+, reuired. Optimum concentraion 50 mM
Mn2+
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]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0035 - 0.004
(3R)-linalyl diphosphate
0.0049
(3S)-linalyl diphosphate
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pH 6.5, 30C
0.0021 - 0.0474
geranyl diphosphate
0.006
neryl diphosphate
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pH 6.5, 30C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0352 - 0.643
geranyl diphosphate
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0017 - 0.255
geranyl diphosphate
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.2
calculated
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
proteolytic modification
sequence contains a putative plastid targeting signal
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
treatment with methyl jasmonate induces transient transcript accumulation in stem tissues
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A595G
shift in product profile, mutant produces 2.4% (+)-car-3-ene, 39% (-)-sabinene, 33.3% terpinolene
A595G/F596L/L599F
shift in product profile, mutant produces 42.3% (+)-car-3-ene, 7.3% (-)-sabinene, 20.1% terpinolene
F596E
shift in product profile, mutant produces 0.5% (+)-car-3-ene, 10.2% (-)-sabinene, 5.7% terpinolene, 70.9% limonene
F596G
shift in product profile, mutant produces 10.0% (+)-car-3-ene, 11.2% (-)-sabinene, 17.3% terpinolene, 27.0% myrcene, 17.0% limonene
F596H
shift in product profile, mutant produces 2.1% (+)-car-3-ene, 46.5% (-)-sabinene, 27.1% terpinolene
F596L
shift in product profile, mutant produces 28.6% (+)-car-3-ene, 42.8% (-)-sabinene, 36.4% terpinolene
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
L599F
shift in product profile, mutant produces 1.5% (+)-car-3-ene, 20.2% (-)-sabinene, 32.2% terpinolene
S589A
shift in product profile, mutant produces 1.2% (+)-car-3-ene, 42.9% (-)-sabinene, 35.5% terpinolene
additional information