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Information on EC 4.2.3.119 - (-)-alpha-pinene synthase
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EC Tree
4.2.3.119 (-)-alpha-pinene synthaseIUBMB Comments
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 . The recombinant PmeTPS1 enzyme from Pseudotsuga menziesii (Douglas fir) gave roughly equal proportions of (-)-alpha-pinene and (-)-camphene plus traces of other monoterpenoids . 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.
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Word Map
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
mono-tps, plpin, avtps1, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(-)-alpha-pinene cyclase
-
-
-
-
(-)-alpha-pinene/(-)-camphene synthase
EC 4.1.99.8
-
-
formerly, part transferred
-
EC 4.2.3.14
-
-
formerly, part transferred
-
TPS-(-)apin1
TPS1
TPS2
additional information
(-)-alpha-pinene/(-)-camphene synthase
-
-
-
-
additional information
cf. EC 4.2.3.120, 4.2.3.121, and 4.2.3.122
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate = (-)-alpha-pinene + diphosphate
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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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.
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CAS REGISTRY NUMBER
COMMENTARY
110637-20-2
for both EC 4.2.3.119 and 4.2.3.120
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(3R)-linalyl diphosphate
(+)-alpha-pinene + diphosphate
-
(3S)-enantiomer is preferred over (3R)-enantiomer
products are (-)-camphene and (-)alpha-pinene
-
?
(3S)-linalyl diphosphate
(+)-alpha-pinene + diphosphate
-
(3S)-enantiomer is preferred over (3R)-enantiomer
products are (+)-camphene and (+)alpha-pinene
-
?
(RS)-alpha-terpinyl diphosphate
limonene + diphosphate
-
-
about 90% limonene, 10% terpinolene
-
?
(3R)-linalyl diphosphate
(-)-alpha-pinene + diphosphate
-
-
products are (-)-alpha-pinene, (-)-beta-pinene, and (-)-camphene
-
?
(3R)-linalyl diphosphate
(-)-alpha-pinene + diphosphate
-
-
products are 17% (-)-alpha-pinene, 9% beta-pinene, 3% camphene, 28% limonene, 9% terpinolene, 23% myrcene, 3% cis-ocimene, 13% trans-ocimene
-
?
(3S)-linalyl diphosphate
(-)-alpha-pinene + diphosphate
-
-
products are (-)-alpha-pinene, (-)-beta-pinene, and (-)-camphene
-
?
(3S)-linalyl diphosphate
(-)-alpha-pinene + diphosphate
-
-
products are 15% (-)-alpha-pinene, 18% beta-pinene, 12% camphene, 11% limonene, 6% terpinolene, 23% myrcene, 3% cis-ocimene, 8% trans-ocimene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
42% terpinolene, 18% (-)-alpha-pinene, 11% (-)-limonene, 10% (-)-beta-pinene plus several minor products
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
-
about 40% (-)-alpha-pinene and 60% (-)-beta-pinene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
products are (-)-alpha-pinene and (-)-beta pinene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
products are 20% (-)-alpha-pinene, 6% (-)-beta-pinene, 26% (-)-limonene, 37% (-)-9-beta-phellandrene, and about 11% other monoterpenes
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
products are 29% (-)-alpha-pinene, 63% (-)-beta-pinene, 1.8% myrcene, 3.6% limonene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
-
products are 31.9% (-)-alpha-pinene and 63.9% (-)-beta-pinene, plus 4.2% myrcene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
products are 54% (-)-(1S,4R)-camphene, followed by 32% (-)-(1S,5S)-alpha-pinene and 7% (-)-(4S)-limonene. (+)-alpha-pinene is produced to about 5% of (-)-alpha-pinene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
products are (-)-alpha-pinene and (-)-beta-pinene, in a ratio of 6:94
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
products are (-)-alpha-pinene and (-)-beta-pinene, in a ratio of about 35:10
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
75.2% (-)-beta-pinene + 13.1% (-)-alpha-pinene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
77.9% (-)-alpha-pinene + 9.6% (-)-beta-pinene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
76.6% (-)-alpha-pinene + 9.9% (-)-beta-pinene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
-
main product, plus lower amounts of (-)-beta-pinene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
products are 79% (-)-alpha-pinene, 4.25 (-)-beta-pinene, almost racemic mixtures of camphene and limonene and small amounts of (+)-alpha-pinene and (+)-beta-pinene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
main products (-)-alpha-pinene and (-)-camphene, plus minor products 3-carene, beta-pinene, limonene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
-
25% (-)-alpha-pinene, 31% (-)-camphene, 24% (-)beta-pinene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
-
main products are (-)-alpha-pinene, (-)-beta-pinene and camphene. Primary deuterium isotope effects suggest that (-)-alpha-pinene and (-)-beta-pinene derive from alternative deprotonation of a common enzymatic intermediate
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
-
products are (-)-alpha-pinene, (-)-beta-pinene, and (-)-camphene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
-
products are (-)-camphene and (-)alpha-pinene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
-
products are (-)-camphene, (-)-alpha-pinene, (-)-beta-pinene, (-)-limonene and myrcene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
-
products are 28% (-)-alpha-pinene, 35% beta-pinene, 24% camphene, 5% limonene, 2% terpinolene, 6% myrcene
-
?
geranyl diphosphate
(-)-alpha-pinene + diphosphate
-
-
reaction proceeds via (3S)-linalyl diphosphate and the (4S)-alpha-terpinyl cation. Products are (-)-alpha-pinene, (-)-beta-pinene and lesser amounts of related olefins
-
?
geranyl diphosphate
alpha-pinene + diphosphate
-
products are 77% alpha-pinene + 14.7% beta-pinene + 5.5 beta-phellandrene
-
?
geranyl diphosphate
alpha-pinene + diphosphate
-
products are 90% alpha-pinene, 10% beta-pinene
-
?
geranyl diphosphate
alpha-pinene + diphosphate
stereochemistry of the product is not specified in the publication
-
-
?
geranyl diphosphate
alpha-pinene + diphosphate
stereochemistry of the product is not specified in the publication
-
-
?
neryl diphosphate
(-)-alpha-pinene + diphosphate
-
-
products are (-)-alpha-pinene, (-)-beta-pinene, and (-)-camphene, products are (-)-camphene and (-)alpha-pinene
-
?
neryl diphosphate
(-)-alpha-pinene + diphosphate
-
-
products are 18% (-)-alpha-pinene, 18% beta-pinene, 12% camphene, 42% limonene, 9% terpinolene, 9% myrcene
-
?
additional information
?
-
entire product set is derived in stereochemically consistent fashion via (-)-3S-linalyl diphosphate as intermediate
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-
?
additional information
?
-
entire product set is derived in stereochemically consistent fashion via (-)-3S-linalyl diphosphate as intermediate
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-
?
additional information
?
-
GC-MS analysis reaction product analysis. Enzyme PlPIN employs geranyl diphosphate as a specific substrate to produce a-pinene as a unique product
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-
?
additional information
?
-
-
GC-MS analysis reaction product analysis. Enzyme PlPIN employs geranyl diphosphate as a specific substrate to produce a-pinene as a unique product
-
-
?
additional information
?
-
no substrates: farnesyl diphosphate, geranygeranyl diphosphate
-
-
?
additional information
?
-
-
each product exhibits the same absolute configuration at the center derived from C-6 of geranyl diphosphate, i e. the isopropylidene-substituted carbon
-
-
?
additional information
?
-
-
enzymes removes the C4-proS-hydrogen of the substrate, the C3 proton of the corresponding pinyl cation, with a stereoselectivity exceeding 78% in the formation of (-)-alpha-pinene
-
-
?
additional information
?
-
-
product distribution varies with deuterium substitution at C4 and C10 of substrate. Kinetic isotope effects strongly indicate multiple bicyclic olefin production through the partitioning of common carbocation intermediates
-
-
?
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 substrates are ionized by the cyclases prior to their achieving the optimum orientation for bicyclization
-
-
?
additional information
?
-
-
substrates geranyl, neryl, and (3S)-linalyl diphosphate yield exclusively the (-)-isomer series, whereas (3R)-linalyl diphosphate affords the (+)-isomers at low rates
-
-
?
additional information
?
-
enzyme AvTPS1 (AvPS or pinene synthase) catalyzes GPP to form alpha-pinene and beta-pinene, the enzyme produces 63% beta-pinene as the major product
-
-
?
additional information
?
-
-
enzyme AvTPS1 (AvPS or pinene synthase) catalyzes GPP to form alpha-pinene and beta-pinene, the enzyme produces 63% beta-pinene as the major product
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
K+
Mg2+
Mn2+
additional information
Mg2+
required, activates, kinetics of wild-type and Q457L and Q457I mutant enzymes, overview
Mn2+
-
or Mn2+, required. Mg2+ is preferred over Mn2+, Mn2+ shows 60-70% of the activity with Mg2+
additional information
no manganese dependency, activity of wild-type and Q457L and Q457I mutant enzymes in the absence or presence of 0.01 mM manganese is similar
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(+)-(1R)-N,N,4-trimethyl-3-cyclohexenamine
-
aza-analogue of terpenyl cation, uncompetitive
(+)-dimethyl-[(1R)-4-methylcyclohex-3-en-1-yl]sulfonium iodide
-
thia-analogue of terpenyl cation, uncompetitive
(-)-(1S)-N,N,4-trimethyl-3-cyclohexenamine
-
aza-analogue of terpenyl cation, uncompetitive
(-)-dimethyl-[(1S)-4-methylcyclohex-3-en-1-yl]sulfonium iodide
-
thia-analogue of terpenyl cation, uncompetitive
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0014
geranyl diphosphate
pH and temperature not specified in the publication
0.006
geranyl diphosphate
-
pH 7.8, temperature not specified in the publication
0.793
geranyl diphosphate
30°C, pH not specified in the publication
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0046
(+)-(1R)-N,N,4-trimethyl-3-cyclohexenamine
-
pH 6.8, 31°C, presence of diphosphate
0.0016
(-)-(1S)-N,N,4-trimethyl-3-cyclohexenamine
-
pH 6.8, 31°C, presence of diphosphate
0.0031
(+)-dimethyl-[(1R)-4-methylcyclohex-3-en-1-yl]sulfonium iodide
-
pH 6.8, 31°C
0.007
(+)-dimethyl-[(1R)-4-methylcyclohex-3-en-1-yl]sulfonium iodide
-
pH 6.8, 31°C, presence of diphosphate
0.0063
(-)-dimethyl-[(1S)-4-methylcyclohex-3-en-1-yl]sulfonium iodide
-
pH 6.8, 31°C, presence of diphosphate
0.0087
(-)-dimethyl-[(1S)-4-methylcyclohex-3-en-1-yl]sulfonium iodide
-
pH 6.8, 31°C
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0019
4-hydroxymercuribenzoate
Abies grandis
-
pH 7.8, temperature not specified in the publication
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
high expression in young leaf, lower expression in medium and old leaves
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
sequence contains a chloroplasttarget signl of 51 amino acids
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
malfunction
physiological function
additional information
evolution
the enzyme belongs to the TPS enzyme superfamily, clade TPS-b, where it is clustered with monoterpene synthases
malfunction
mutation Q456L in the alpha-domain (catalytic domain) causes a reduction in pigmentation (PSmut)
malfunction
replacement of residue Q457 with three other amino acids I, K, and V, elevates the activity of the enzyme, while Q457P shows reduced activity
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
physiological function
<