Information on EC 4.2.3.121 - (+)-alpha-pinene synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
4.2.3.121
-
RECOMMENDED NAME
GeneOntology No.
(+)-alpha-pinene synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate = (+)-alpha-pinene + diphosphate
show the reaction diagram
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-alpha-pinene-forming]
Cyclase I of Salvia officinalis (sage) gives about equal parts (+)-alpha-pinene and (+)-camphene, whereas cyclase III gives about equal parts of (+)-alpha-pinene and (+)-beta-pinene. (3R)-Linalyl diphosphate can also be used by the enzyme in preference to (3S)-linalyl diphosphate. The 4-pro-R-hydrogen of geranyl diphosphate is lost. Requires Mg2+ (preferred to Mn2+) [1-4]. With synthase II of Pinus taeda (loblolly pine) (+)-alpha-pinene was the only product [5,6]. Requires Mn2+ (preferred to Mg2+). See also EC 4.2.3.122, (+)-beta-pinene synthase, and EC 4.2.3.116, (+)-camphene synthase.
CAS REGISTRY NUMBER
COMMENTARY hide
11637-21-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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UniProt
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
(+)-alpha-pinene + diphosphate
show the reaction diagram
(3S)-linalyl diphosphate
(+)-alpha-pinene + diphosphate
show the reaction diagram
-
-
products are 9% (+)-alpha-pinene, 9% camphene, 34% limonene, 28%% terpinolene, 11% myrcene, 2% cis-ocimene, 6% trans-ocimene
-
?
(3S)-linalyl diphosphate
(-)-alpha-pinene + diphosphate
show the reaction diagram
-
(3R)-enantiomer is preferred over (3S)-enantiomer
products are (-)-camphene and (-)alpha-pinene
-
?
(RS)-alpha-terpinyl diphosphate
limonene + diphosphate
show the reaction diagram
-
-
about 90% limonene, 10% terpinolene
-
?
geranyl diphosphate
(+)-alpha-pinene + diphosphate
show the reaction diagram
geranyl diphosphate
alpha-pinene + diphosphate
show the reaction diagram
neryl diphosphate
(+)-alpha-pinene + diphosphate
show the reaction diagram
additional information
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
NH4+
may substitute for K+ for optimum activity
additional information
-
not effective: Li+, Na+, Rb+, Cs+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-(1R)-N,N,4-trimethyl-3-cyclohexenamine
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aza-analogue of terpenyl cation, uncompetitive
(+)-dimethyl-[(1R)-4-methylcyclohex-3-en-1-yl]sulfonium iodide
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thia-analogue of terpenyl cation, uncompetitive/noncompetitive
(-)-(1S)-N,N,4-trimethyl-3-cyclohexenamine
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aza-analogue of terpenyl cation, uncompetitive
(-)-dimethyl-[(1S)-4-methylcyclohex-3-en-1-yl]sulfonium iodide
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thia-analogue of terpenyl cation, uncompetitive/noncompetitve
4-hydroxymercuribenzoate
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diphosphate
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geranyl diphosphate
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substrate inhibition above 0.05 mM
N-ethylmaleimide
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.004
(3R)-linalyl diphosphate
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pH 6.5, 30°C
0.0049
(3S)-linalyl diphosphate
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pH 6.5, 30°C
0.0025
(RS)-alpha-terpinyl diphosphate
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pH 5.8, 31°C
0.001 - 0.0474
geranyl diphosphate
0.006
neryl diphosphate
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pH 6.5, 30°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.012
geranyl diphosphate
Lavandula angustifolia
Q2XSC6
pH 7.5, 23°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.253
geranyl diphosphate
Lavandula angustifolia
Q2XSC6
pH 7.5, 23°C
175
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.001 - 0.002
(+)-(1R)-N,N,4-trimethyl-3-cyclohexenamine
0.0058 - 0.0092
(+)-dimethyl-[(1R)-4-methylcyclohex-3-en-1-yl]sulfonium iodide
0.0007 - 0.0011
(-)-(1S)-N,N,4-trimethyl-3-cyclohexenamine
0.004 - 0.0071
(-)-dimethyl-[(1S)-4-methylcyclohex-3-en-1-yl]sulfonium iodide
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.2
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assay in hexane
7
optimum for total enzymic activity
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.7
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half-maximal activity
6.5
half-maximal reaction velocity
7.5
half-maximal reaction velocity
7.9
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half-maximal activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
optimum for total enzymic activity
33
optimum for maximum formation of alpha-pinene
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20
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55% of maximum activity
58
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20% of maximum activity
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5
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or below, isoelectric focusing
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
-
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
64500
x * 64500, SDS-PAGE of recombinant protein lacking transit peptide
65000
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gel fitration
70300
x * 70300, calculated
95000
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gel filtration
100000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
proteolytic modification
sequence contains a putative transit peptide
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
modeling of structure against the tobacco sesquiterpene synthase 5-epi-aristolochene synthase and the monoterpene synthase bornyl diphosphate synthase from common sage
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
diisopropyl ether
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enzyme is active in hexane, hexadecane, diisopropyl ether, or distilled water, and gives rise to the same olefin distribution of 25% (+)-alpha-pinene, 25% (+)-camphene 43% (+)-limonene, 7% myrcene
hexadecane
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enzyme is active in hexane, hexadecane, diisopropyl ether, or distilled water, and gives rise to the same olefin distribution of 25% (+)-alpha-pinene, 25% (+)-camphene 43% (+)-limonene, 7% myrcene
hexane
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enzyme is active in hexane, hexadecane, diisopropyl ether, or distilled water, and gives rise to the same olefin distribution of 25% (+)-alpha-pinene, 25% (+)-camphene 43% (+)-limonene, 7% myrcene. Reactions run in hexane generate product at roughly one-third the rate of companion assays in which the lyophilized protein is rehydrated in distilled water. Relative proportion of alpha-pinene in product distribution is optimal in presence of 5-10% water
additional information
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enzyme is active in hexane, hexadecane, diisopropyl ether, or distilled water, and gives rise to the same olefin distribution of 25% (+)-alpha-pinene, 25% (+)-camphene 43% (+)-limonene, 7% myrcene
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
lyophilization and rehydration in destilled water results in loss of about 10% of activity
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichi coli
expression in Escherichia coli