4.2.3.107: (+)-car-3-ene synthase
This is an abbreviated version!
For detailed information about (+)-car-3-ene synthase, go to the full flat file.
Reaction
Synonyms
(+)-3-carene synthase, 3-carene cyclase, 3-carene synthase, 3CAR, 3CARS, JF67, Li3CARS, TPS-3car1, TPS-3car2, TPS-3car3
ECTree
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Substrates Products
Substrates Products on EC 4.2.3.107 - (+)-car-3-ene synthase
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REACTION DIAGRAM
(3R)-linalyl diphosphate
? + diphosphate
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-
the velocity of the reaction with the (3S)-linalyl enantiomer is 25fold greater than the velocity with the (3R)-enantiomer and twice that of the natural substrate, geranyl diphosphate. Cyclization of the linalyl intermediate is faster than the coupled isomerization and cyclization of the geranyl substrate
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?
(3S)-linalyl diphosphate
(+)-car-3-ene + diphosphate
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-
more than 99.9% optically pure
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?
(3S)-linalyl diphosphate
? + diphosphate
-
-
the velocity of the reaction with the (3S)-linalyl enantiomer is 25fold greater than the velocity with the (3R)-enantiomer and twice that of the natural substrate, geranyl diphosphate. Cyclization of the linalyl intermediate is faster than the coupled isomerization and cyclization of the geranyl substrate
-
?
neryl diphosphate
limonene + diphosphate
low activity, neryl diphosphate is transformed into limonene (33%), alpha-terpinolene (29%) and alpha-thujene (20%) as main products, and minor amounts of a few other monoterpenes including 3-carene (8.5%)
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-
?
geranyl diphosphate
(+)-car-3-ene + diphosphate
geranyl diphosphate is converted mainly to 3-carene
-
-
?
geranyl diphosphate
(+)-car-3-ene + diphosphate
-
78% (+)-car-3-ene plus 11% terpinolene plus minor products. No detection of (-)-car-3-ene
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?
geranyl diphosphate
(+)-car-3-ene + diphosphate
-
major product, plus some terpinolene
-
?
geranyl diphosphate
(+)-car-3-ene + diphosphate
-
wild-type produces 46.2% (+)-car-3-ene, 8.8% (-)-sabinene, 29.7% terpinolene
-
?
geranyl diphosphate
(+)-car-3-ene + diphosphate
-
wild-type produces 49% (+)-car-3-ene, 8.7% (-)-sabinene, 24.7% terpinolene
-
?
geranyl diphosphate
(+)-car-3-ene + diphosphate
-
wild-type produces 67.5% (+)-car-3-ene, 6.9% (-)-sabinene, 15.4% terpinolene
-
?
geranyl diphosphate
(+)-car-3-ene + diphosphate
-
reaction proceeds via an enzyme-bound (3S)-linalyl diphosphate intermediate
more than 99.9% optically pure
-
?
geranyl diphosphate
(+)-car-3-ene + diphosphate
-
the H located at C1 in the geranyl substrate resides at C5 of product (+)-car-3-ene. The 5-proR hydrogen is eliminated during cyclopropyl ring closure. Cyclopropyl ring formation occurs via a (4S)-alpha-terpinyl cation derived from the anti-endo-cyclization of a (3S)-linalyl diphosphate intermediate
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-
?
geranyl diphosphate
(+)-car-3-ene + diphosphate
-
73% (+)-3-carene, 13% (-)-limonene, 6% myrcene, 4% 4-carene and 1% beta-phellandrene
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?
?
-
the recombinant Li3CARS converted geranyl diphosphate (GPP) into 3-carene as the major product, Li3CARS also accepts neryl diphosphate (NPP) as a substrate to produce multiple products including a small amount of 3-carene. The catalytic efficiency of Li3CARS to produce 3-carene is about 13fold higher for GPP than NPP. Ligand identification by GC-MS analysis
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-
?
additional information
?
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-
the recombinant Li3CARS converted geranyl diphosphate (GPP) into 3-carene as the major product, Li3CARS also accepts neryl diphosphate (NPP) as a substrate to produce multiple products including a small amount of 3-carene. The catalytic efficiency of Li3CARS to produce 3-carene is about 13fold higher for GPP than NPP. Ligand identification by GC-MS analysis
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?
additional information
?
-
no oxygenated or phosphorylated monoterpenes are found in detectable amounts
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?
additional information
?
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-
no oxygenated or phosphorylated monoterpenes are found in detectable amounts
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?
additional information
?
-
poor substrate: neryl diphosphate. No substrates: farnesyl diphosphate, geranylgeranyl diphosphate
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?
additional information
?
-
poor substrate: neryl diphosphate. No substrates: farnesyl diphosphate, geranylgeranyl diphosphate
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-
?
additional information
?
-
poor substrate: neryl diphosphate. No substrates: farnesyl diphosphate, geranylgeranyl diphosphate
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-
?
additional information
?
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-
poor substrate: neryl diphosphate. No substrates: farnesyl diphosphate, geranylgeranyl diphosphate
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?