4.2.3.121: (+)-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 4.2.3.121
Reaction
Synonyms
(+)-alpha-pinene cyclase, (+)-pinene cyclase, alpha pinene sythase, alpha-pinene sythase, AvPS, AvTPS1, cyclase I, cyclase III, limonene synthase, LIMS, More, pinene synthase, PINS, PlPIN, TPS-(+)apin1, TPS1
ECTree
4.2.3.121 (+)-alpha-pinene synthaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 4.2.3.121 - (+)-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
(3S)-linalyl diphosphate
(+)-alpha-pinene + diphosphate
-
-
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
-
(3R)-enantiomer is preferred over (3S)-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 62% (+)-alpha-pinene, 6% camphene, 11% limonene, 7% terpinolene, 10% myrcene, 1% cis-ocimene, 4% trans-ocimene
-
?
(3R)-linalyl diphosphate
(+)-alpha-pinene + diphosphate
-
(3R)-enantiomer is preferred over (3S)-enantiomer
products are (+)-camphene and (+)alpha-pinene
-
?
geranyl diphosphate
(+)-alpha-pinene + diphosphate
-
products are 39% (R)-(+)-limonene, 22% terpinolene, 16% (1R,5S)-(+)-camphene, 14% (1R,5R)-(+)-alpha-pinene, 8% beta-myrcene and traces of alpha-phellandrene. Preferential formation of the (+)-enantiomers with 94% enantiomeric purity for (1R,5R)-(+)-alpha-pinene. Product pattern changes to 46% limonene, 9% terpinolene, 23% alpha-pinene, 5% beta-myrcene and 4% alpha-phellandrene, when Mn2+ is supplied instead of Mg2+
-
?
geranyl diphosphate
(+)-alpha-pinene + diphosphate
-
91.7% (+)-alpha-pinene
-
?
geranyl diphosphate
(+)-alpha-pinene + diphosphate
-
88.2% of products
-
?
geranyl diphosphate
(+)-alpha-pinene + diphosphate
-
products are 97% (+)-alpha-pinene, 3% (-)-alpha-pinene
-
?
geranyl diphosphate
(+)-alpha-pinene + diphosphate
-
-
31% (+)-alpha-pinene, 29% (+)-camphene, 36% (+)-alpha-pinene, 45% (+)beta-pinene
-
?
geranyl diphosphate
(+)-alpha-pinene + diphosphate
-
-
products are (+)-camphene and (+)alpha-pinene
-
?
geranyl diphosphate
(+)-alpha-pinene + diphosphate
-
-
products are (+)-camphene, (+)-alpha-pinene and (+)-limonene
-
?
geranyl diphosphate
(+)-alpha-pinene + diphosphate
-
-
products are 25% (+)-alpha-pinene, 25% (+)-camphene, 43% (+)-limonene, and 7% myrcene. Reaction in organic solvent gives the same olefin distribution as in aqueous buffer
-
?
geranyl diphosphate
(+)-alpha-pinene + diphosphate
-
-
products are 49% (+)-alpha-pinene, 30% camphene, 10% limonene, 5% terpinolene, 6% myrcene
-
?
geranyl diphosphate
(+)-alpha-pinene + diphosphate
-
-
products of cyclase I are (+)-alpha-pinene and (+)-camphene, products of cyclase III are (+)-alpha-pinene and (+)-beta-pinene
-
?
geranyl diphosphate
(+)-alpha-pinene + diphosphate
-
-
reaction proceeds stereoselectively to (+)-borneol, which is oxidised to (+)-camphor. Configuration at C1 of geranyl pyrophosphate is retained in the enzymatic transformations. The 1-proR-hydrogen of neryl diphosphate gives rise to the exo-alpha-hydrogen of (+)-camphor, and the 1-proS-hydrogen to the endo-alpha-hydrogen, whereas the 1-proS-hydrogen of this precursor gives rise to the exo-alpha-hydrogen of the enantiomeric (-)-camphor, and the 1-proR-hydrogen to the endo-alpha-hydrogen. The configuration at C1 of neryl pyrophosphate is inverted in the cyclizations to alpha- and beta-pinene, and fully consistent with the cyclization model
-
?
geranyl diphosphate
(+)-alpha-pinene + diphosphate
-
-
reaction proceeds via (3R)-linalyl diphosphate and the (4R)-alpha-terpinyl cation. Products are (+)-alpha-pinene, and lesser amounts of related olefins
-
?
geranyl diphosphate
alpha-pinene + diphosphate
-
93% alpha-pinene plus 4% limonene, 1.6% alpha-phellandrene, 1,1% alpha-terpinolene
-
?
geranyl diphosphate
alpha-pinene + diphosphate
-
90.6% alpha-pinene plus 6% limonene, 1.7% alpha-phellandrene, 1,6% alpha-terpinolene
-
?
neryl diphosphate
(+)-alpha-pinene + diphosphate
-
-
products are (+)-camphene and (+)alpha-pinene
-
?
neryl diphosphate
(+)-alpha-pinene + diphosphate
-
-
products are 14% (+)-alpha-pinene, 9% camphene, 62% limonene, 8% terpinolene, 6% myrcene
-
?
additional information
?
-
no substrate: geranylgeranyl diphosphate
-
-
?
additional information
?
-
no substrate: geranylgeranyl diphosphate
-
-
?
additional information
?
-
GC-MS analysis reaction product analysis. Enzyme PlPIN employs geranyl diphosphate as a specific substrate to produce alpha-pinene as a unique product
-
-
?
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-proR-hydrogen of the substrate, the C3 proton trans to the dimethyl bridge of the pinyl nucleus, with a stereoselectivity exceeding 94% 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
?
-
enzyme AvTPS1 (AvPS or pinene synthase) catalyzes geranyl diphosphate to form alpha-pinene and beta-pinene, the enzyme produces 63% beta-pinene as the major product
-
-
?
