Information on EC 4.2.3.119 - (-)-alpha-pinene synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
4.2.3.119
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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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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
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fenchol biosynthesis II
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Metabolic pathways
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monoterpene biosynthesis
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Monoterpenoid biosynthesis
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oleoresin monoterpene volatiles biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-alpha-pinene-forming]
Cyclase II of Salvia officinalis (sage) gives about equal parts (-)-alpha-pinene, (-)-beta-pinene and (-)-camphene, plus traces of other monoterpenoids. (3S)-Linalyl diphosphate can also be used by the enzyme in preference to (3R)-linalyl diphosphate. The 4-pro-S-hydrogen of geranyl diphosphate is lost. Requires Mg2+ (preferred to Mn2+) [1-6]. The enzyme from Abies grandis (grand fir) gives roughly equal parts (-)-alpha-pinene and (-)-beta-pinene. However the clone ag11 gave 35% (-)-limonene, 24% (-)-alpha-pinene and 20% (-)-beta-phellandrene. It requires Mn2+ and K+ (Mg2+ is ineffective) [7-10]. Synthase I from Pinus taeda (loblolly pine) produces (-)-alpha-pinene with traces of (-)-beta-pinene and requires Mn2+ (preferred to Mg2+) [11,12]. The enzyme from Picea sitchensis (Sika spruce) forms 70% (-)-alpha-pinene and 30% (-)-beta-pinene [13]. The recombinant PmeTPS1 enzyme from Pseudotsuga menziesii (Douglas fir) gave roughly equal proportions of (-)-alpha-pinene and (-)-camphene plus traces of other monoterpenoids [14]. See also EC 4.2.3.120, (-)-beta-pinene synthase; EC 4.2.3.117, (-)-camphene synthase; EC 4.2.3.16, (-)-limonene synthase; and EC 4.2.3.52, (-)-beta-phellandrene synthase.
CAS REGISTRY NUMBER
COMMENTARY hide
110637-20-2
for both EC 4.2.3.119 and 4.2.3.120
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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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
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
in isoform TPS3-silenced plants, alpha-pinene, beta-pinene and beta-phellandrene contents decrease by more than 80%, whereas beta-myrcene is unchanged
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
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(3S)-enantiomer is preferred over (3R)-enantiomer
products are (-)-camphene and (-)alpha-pinene
-
?
(3R)-linalyl diphosphate
(-)-alpha-pinene + diphosphate
show the reaction diagram
(3S)-linalyl diphosphate
(+)-alpha-pinene + diphosphate
show the reaction diagram
-
(3S)-enantiomer is preferred over (3R)-enantiomer
products are (+)-camphene and (+)alpha-pinene
-
?
(3S)-linalyl diphosphate
(-)-alpha-pinene + diphosphate
show the reaction diagram
(RS)-alpha-terpinyl diphosphate
limonene + diphosphate
show the reaction diagram
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-
about 90% limonene, 10% terpinolene
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?
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
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
(-)-(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
4-hydroxymercuribenzoate
alpha-pinene
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diethyldicarbonate
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diphosphate
geranyl diphosphate
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substrate inhibition above 0.05 mM
N-ethylmaleimide
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phosphate
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0035 - 0.0036
(3R)-linalyl diphosphate
0.0035 - 0.0036
(3S)-linalyl diphosphate
0.009
(RS)-alpha-terpinyl diphosphate
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pH 6.8, 31°C
0.0014 - 0.793
geranyl diphosphate
0.0021 - 0.0023
neryl diphosphate
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0046
(+)-(1R)-N,N,4-trimethyl-3-cyclohexenamine
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pH 6.8, 31°C, presence of diphosphate
0.0031 - 0.007
(+)-dimethyl-[(1R)-4-methylcyclohex-3-en-1-yl]sulfonium iodide
0.0016
(-)-(1S)-N,N,4-trimethyl-3-cyclohexenamine
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pH 6.8, 31°C, presence of diphosphate
0.0063 - 0.0087
(-)-dimethyl-[(1S)-4-methylcyclohex-3-en-1-yl]sulfonium iodide
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0019
4-hydroxymercuribenzoate
Abies grandis
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pH 7.8, temperature not specified in the publication
0.64
diethyldicarbonate
Abies grandis
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pH 7.8, temperature not specified in the publication
0.17
diphosphate
Abies grandis
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pH 7.8, temperature not specified in the publication
51
phosphate
Abies grandis
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pH 7.8, temperature not specified in the publication
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.7
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half-maximal activity
6.2
half-maximal reaction velocity
7
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80% of maximum activity
7.8
half-maximal reaction velocity
7.9
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half-maximal activity
8.3
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80% of maximum activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
trace expression
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
63000
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gel filtration
64500
x * 64500, SDS-PAGE of recombinant protein lacking transit peptide
65000
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gel fitration
69400
x * 69400, calculated
70750
x * 70750, calculated
71500
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x * 71500, calculated
95000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
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1 * 62000, SDS-PAGE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
proteolytic modification
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
modeling of amino acid sequence onto the crystal structures of tobacco 5-epi-aristolochene synthase and bornyl diphosphate synthase and comparison with (-)-camphene synthase
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
purified enzyme, stable at 4°C, in 50 mM Hepes, pH 7.8, for at least 3 weeks, at -20°C, stable for sevceral months
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
partial
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Corynebacterium glutamicum
expression in Escherichia coli
expression in Escherichia coli; expression in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression is induced upon wounding or methyljasmonate treatment
significant increase in transcript level in the leaders of lateral branches of weevil-attacked and mechanically wounded trees
transcript levels are transiently reduced following mechanical wounding or fungal elicitor treatment
under a photoperiod of 12 h/12 h (light/dark), the abundance of QH6 transcripts fluctuates in a diurnal pattern that ebbs around 3 h before daybreak, i.e. 9th h in the dark phase, and peaks after 9 h in light, i.e. 9th h in the light phase. The contents of (-)--pinene in juvenile leaves and in emitted volatiles also vary in a diurnal rhythm, correlating strongly with mRNA accumulation
upon methyljasmonate treatment, expression is significantly induced in medium and old leaves
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C372S
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replacement with corresponding residue of (-)-camphene synthase, 97% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene, while the levels of total pinenes remains relatively constant
C372S/C480S
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replacement with corresponding residue of (-)-camphene synthase, 72% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene
C372S/F597W
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replacement with corresponding residue of (-)-camphene synthase, 100% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene
C372S/F597W/S485C/F597W
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replacement with corresponding residue of (-)-camphene synthase, 99% of wild-type activity. Mutant produces about 80%(-)-alpha-pinene and 10% (-)-beta-pinene
C372S/S485C
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replacement with corresponding residue of (-)-camphene synthase, 92% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene
C480S
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replacement with corresponding residue of (-)-camphene synthase, 97% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene, while the levels of total pinenes remains relatively constant
C480S/F597W
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replacement with corresponding residue of (-)-camphene synthase, 7% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene
C480S/S485C
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replacement with corresponding residue of (-)-camphene synthase, 70% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene
F597W
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replacement with corresponding residue of (-)-camphene synthase, 73% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene, while the levels of total pinenes remains relatively constant
S485C
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replacement with corresponding residue of (-)-camphene synthase, 100% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene, while the levels of total pinenes remains relatively constant
S485C/F597W
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replacement with corresponding residue of (-)-camphene synthase, 68% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene
additional information
Renatured/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
renaturation after SDS-PAGE in 1% Tween 20
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
co-expression with over-expressed native 1-deoxy-D-xylulose-5-phosphate synthase and isopentenyl diphosphate isomerase from Corynebacterium glutamicum plus geranyl diphosphate synthase from Abies grandis leads to synthesis of up to 27 microg alpha-pinene per g cell weight