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Literature summary extracted from

  • Croteau, R.; Satterwhite, D.M.
    Biosynthesis of monoterpenes: Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (-)-pinene cyclases from sage (1989), J. Biol. Chem., 264, 15309-15315.
    View publication on PubMed

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
4.2.3.113 0.0021
-
geranyl diphosphate pH 6.5, 30°C Salvia officinalis
4.2.3.113 0.0021
-
neryl diphosphate pH 6.5, 30°C Salvia officinalis
4.2.3.113 0.003
-
geranyl diphosphate pH 6.5, 30°C Salvia officinalis
4.2.3.113 0.0035
-
(3S)-linalyl diphosphate pH 6.5, 30°C Salvia officinalis
4.2.3.113 0.0035
-
(3R)-linalyl diphosphate pH 6.5, 30°C Salvia officinalis
4.2.3.113 0.004
-
(3R)-linalyl diphosphate pH 6.5, 30°C Salvia officinalis
4.2.3.113 0.0049
-
(3S)-linalyl diphosphate pH 6.5, 30°C Salvia officinalis
4.2.3.113 0.006
-
neryl diphosphate pH 6.5, 30°C Salvia officinalis
4.2.3.119 0.0021
-
neryl diphosphate pH 6.5, 30°C Salvia officinalis
4.2.3.119 0.003
-
geranyl diphosphate pH 6.5, 30°C Salvia officinalis
4.2.3.119 0.0035
-
(3S)-linalyl diphosphate pH 6.5, 30°C Salvia officinalis
4.2.3.119 0.0035
-
(3R)-linalyl diphosphate pH 6.5, 30°C Salvia officinalis
4.2.3.120 0.003
-
geranyl diphosphate pH 6.5, 30°C Salvia officinalis
4.2.3.121 0.0021
-
geranyl diphosphate pH 6.5, 30°C Salvia officinalis
4.2.3.121 0.004
-
(3R)-linalyl diphosphate pH 6.5, 30°C Salvia officinalis
4.2.3.121 0.0049
-
(3S)-linalyl diphosphate pH 6.5, 30°C Salvia officinalis
4.2.3.121 0.006
-
neryl diphosphate pH 6.5, 30°C Salvia officinalis

Organism

EC Number Organism UniProt Comment Textmining
4.2.3.113 Salvia officinalis
-
-
-
4.2.3.119 Salvia officinalis
-
-
-
4.2.3.120 Salvia officinalis
-
-
-
4.2.3.121 Salvia officinalis
-
-
-
4.2.3.122 Salvia officinalis
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.3.113 (3R)-linalyl diphosphate
-
Salvia officinalis terpinolene + diphosphate products are 17% (-)-alpha-pinene, 9% beta-pinene, 3% camphene, 28% limonene, 9% terpinolene, 23% myrcene, 3% cis-ocimene, 13% trans-ocimene ?
4.2.3.113 (3R)-linalyl diphosphate
-
Salvia officinalis terpinolene + diphosphate products are 62% (+)-alpha-pinene, 6% camphene, 11% limonene, 7% terpinolene, 10% myrcene, 1% cis-ocimene, 4% trans-ocimene ?
4.2.3.113 (3S)-linalyl diphosphate
-
Salvia officinalis terpinolene + diphosphate products are 15% (-)-alpha-pinene, 18% beta-pinene, 12% camphene, 11% limonene, 6% terpinolene, 23% myrcene, 3% cis-ocimene, 8% trans-ocimene ?
4.2.3.113 (3S)-linalyl diphosphate
-
Salvia officinalis terpinolene + diphosphate products are 9% (+)-alpha-pinene, 9% camphene, 34% limonene, 28%% terpinolene, 11% myrcene, 2% cis-ocimene, 6% trans-ocimene ?
4.2.3.113 geranyl diphosphate
-
Salvia officinalis terpinolene + diphosphate products are 28% (-)-alpha-pinene, 35% beta-pinene, 24% camphene, 5% limonene, 2% terpinolene, 6% myrcene ?
4.2.3.113 geranyl diphosphate
-
Salvia officinalis terpinolene + diphosphate products are 49% (+)-alpha-pinene, 30% camphene, 10% limonene, 5% terpinolene, 6% myrcene ?
4.2.3.113 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 substratse are ionized by the cyclases prior to their achieving the optimum orientation for bicyclization Salvia officinalis ?
-
?
4.2.3.113 neryl diphosphate
-
Salvia officinalis terpinolene + diphosphate products are 14% (+)-alpha-pinene, 9% camphene, 62% limonene, 8% terpinolene, 6% myrcene ?
4.2.3.113 neryl diphosphate
-
Salvia officinalis terpinolene + diphosphate products are 18% (-)-alpha-pinene, 18% beta-pinene, 12% camphene, 42% limonene, 9% terpinolene, 9% myrcene ?
4.2.3.119 (3R)-linalyl diphosphate
-
Salvia officinalis (-)-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 ?
4.2.3.119 (3S)-linalyl diphosphate
-
Salvia officinalis (-)-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 ?
4.2.3.119 geranyl diphosphate
-
Salvia officinalis (-)-alpha-pinene + diphosphate products are 28% (-)-alpha-pinene, 35% beta-pinene, 24% camphene, 5% limonene, 2% terpinolene, 6% myrcene ?
4.2.3.119 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 Salvia officinalis ?
-
?
4.2.3.119 neryl diphosphate
-
Salvia officinalis (-)-alpha-pinene + diphosphate products are 18% (-)-alpha-pinene, 18% beta-pinene, 12% camphene, 42% limonene, 9% terpinolene, 9% myrcene ?
4.2.3.120 geranyl diphosphate
-
Salvia officinalis (-)-beta-pinene products are 28% (-)-alpha-pinene, 35% (-)-beta-pinene, 24% (+)-camphene, 5% (+)-limonene, plus some terpinolene and myrcene ?
4.2.3.120 additional information bicyclic products pinene and camphene are derived via the cyclization of the bound, tertiary intermediate (3R)-linalyl diphosphate. Limonene is formed via conformational foldings in addition to the 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 Salvia officinalis ?
-
?
4.2.3.121 (3R)-linalyl diphosphate
-
Salvia officinalis (+)-alpha-pinene + diphosphate products are 62% (+)-alpha-pinene, 6% camphene, 11% limonene, 7% terpinolene, 10% myrcene, 1% cis-ocimene, 4% trans-ocimene ?
4.2.3.121 (3S)-linalyl diphosphate
-
Salvia officinalis (+)-alpha-pinene + diphosphate products are 9% (+)-alpha-pinene, 9% camphene, 34% limonene, 28%% terpinolene, 11% myrcene, 2% cis-ocimene, 6% trans-ocimene ?
4.2.3.121 geranyl diphosphate
-
Salvia officinalis (+)-alpha-pinene + diphosphate products are 49% (+)-alpha-pinene, 30% camphene, 10% limonene, 5% terpinolene, 6% myrcene ?
4.2.3.121 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 Salvia officinalis ?
-
?
4.2.3.121 neryl diphosphate
-
Salvia officinalis (+)-alpha-pinene + diphosphate products are 14% (+)-alpha-pinene, 9% camphene, 62% limonene, 8% terpinolene, 6% myrcene ?
4.2.3.122 geranyl diphosphate
-
Salvia officinalis (+)-alpha-pinene + diphosphate products are (+)-alpha-pinene, (+)-camphene, and lesser amounts of (+)-limonene, myrcene, and terpinolene. The bicyclic products of pinene and camphene are derived via the cyclization of the cisoid, anti-endo-conformers of the bound, tertiary allylic intermediate (3R)-linalyl diphosphate. A preassociation mechanism of geranyl diphosphate is suggested in which optimum folding of the terpenyl chain precedes the initial ionization step ?
4.2.3.122 linalyl diphosphate
-
Salvia officinalis myrcene + diphosphate products are disproportionately high levels of acyclic olefins myrcene and ocimene and monocyclic olefins limonene and terpinolene. Limonene is formed via conformational foldings in addition to the cisoid, anti-endo-pattern ?
4.2.3.122 neryl diphosphate
-
Salvia officinalis myrcene + diphosphate products are disproportionately high levels of acyclic olefins myrcene and ocimene and monocyclic olefins limonene and terpinolene. Limonene is formed via conformational foldings in addition to the cisoid, anti-endo-pattern ?

Synonyms

EC Number Synonyms Comment Organism
4.2.3.113 (+)-pinene cyclase
-
Salvia officinalis
4.2.3.113 (-)-pinene cyclase
-
Salvia officinalis
4.2.3.119 (-)-pinene cyclase
-
Salvia officinalis
4.2.3.121 (+)-pinene cyclase
-
Salvia officinalis