4.2.3.119: (-)-alpha-pinene synthase
This is an abbreviated version!
For detailed information about (-)-alpha-pinene synthase, go to the full flat file.
Word Map on EC 4.2.3.119
Reaction
Synonyms
(-)-alpha-pinene cyclase, (-)-alpha-pinene/(-)-camphene synthase, (-)-limonene/(-)-alpha-pinene synthase, (-)-pinene cyclase, (-)-pinene synthase, ag6, ag9, alpha pinene sythase, alpha-pinene sythase, AvPS, AvTPS1, camphene synthase, cyclase II, EC 4.1.99.8, EC 4.2.3.14, LPS, mono-tps, More, pinene synthase, pinene-synthase, PlPIN, PT1, QH6, TPS-(-)apin1, TPS-(-)bpin2, TPS1, TPS2, TPS3
ECTree
4.2.3.119 (-)-alpha-pinene synthaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 4.2.3.119 - (-)-alpha-pinene synthase
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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
-
-
?
additional information
?
-
entire product set is derived in stereochemically consistent fashion via (-)-3S-linalyl diphosphate as intermediate
-
-
?
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
?
-
-
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
-
-
?
