4.2.3.119 (3R)-linalyl diphosphate (3S)-enantiomer is preferred over (3R)-enantiomer Salvia officinalis (+)-alpha-pinene + diphosphate products are (-)-camphene and (-)alpha-pinene ? 418147 4.2.3.119 (3R)-linalyl diphosphate - Salvia officinalis (-)-alpha-pinene + diphosphate products are (-)-alpha-pinene, (-)-beta-pinene, and (-)-camphene ? 418149 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 ? 418149 4.2.3.119 (3S)-linalyl diphosphate (3S)-enantiomer is preferred over (3R)-enantiomer Salvia officinalis (+)-alpha-pinene + diphosphate products are (+)-camphene and (+)alpha-pinene ? 418156 4.2.3.119 (3S)-linalyl diphosphate - Salvia officinalis (-)-alpha-pinene + diphosphate products are (-)-alpha-pinene, (-)-beta-pinene, and (-)-camphene ? 418159 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 ? 418159 4.2.3.119 (RS)-alpha-terpinyl diphosphate - Salvia officinalis limonene + diphosphate about 90% limonene, 10% terpinolene ? 418184 4.2.3.119 geranyl diphosphate - Wurfbainia villosa alpha-pinene + diphosphate - ? 409492 4.2.3.119 geranyl diphosphate - Paeonia lactiflora alpha-pinene + diphosphate - ? 409492 4.2.3.119 geranyl diphosphate - Gossypium hirsutum alpha-pinene + diphosphate products are 77% alpha-pinene + 14.7% beta-pinene + 5.5 beta-phellandrene ? 409492 4.2.3.119 geranyl diphosphate - Gossypium hirsutum alpha-pinene + diphosphate products are 90% alpha-pinene, 10% beta-pinene ? 409492 4.2.3.119 geranyl diphosphate stereochemistry of the product is not specified in the publication Wurfbainia villosa alpha-pinene + diphosphate - ? 409492 4.2.3.119 geranyl diphosphate stereochemistry of the product is not specified in the publication Paeonia lactiflora alpha-pinene + diphosphate - ? 409492 4.2.3.119 geranyl diphosphate - Pinus taeda (-)-alpha-pinene + diphosphate - ? 418647 4.2.3.119 geranyl diphosphate - Salvia officinalis (-)-alpha-pinene + diphosphate 25% (-)-alpha-pinene, 31% (-)-camphene, 24% (-)beta-pinene ? 418647 4.2.3.119 geranyl diphosphate - Abies grandis (-)-alpha-pinene + diphosphate 42% terpinolene, 18% (-)-alpha-pinene, 11% (-)-limonene, 10% (-)-beta-pinene plus several minor products ? 418647 4.2.3.119 geranyl diphosphate - Abies grandis (-)-alpha-pinene + diphosphate about 40% (-)-alpha-pinene and 60% (-)-beta-pinene ? 418647 4.2.3.119 geranyl diphosphate - Pinus taeda (-)-alpha-pinene + diphosphate main product, plus lower amounts of (-)-beta-pinene ? 418647 4.2.3.119 geranyl diphosphate - Pseudotsuga menziesii (-)-alpha-pinene + diphosphate main products (-)-alpha-pinene and (-)-camphene, plus minor products 3-carene, beta-pinene, limonene ? 418647 4.2.3.119 geranyl diphosphate - Salvia officinalis (-)-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 ? 418647 4.2.3.119 geranyl diphosphate - Abies grandis (-)-alpha-pinene + diphosphate products are (-)-alpha-pinene and (-)-beta pinene ? 418647 4.2.3.119 geranyl diphosphate - Artemisia annua (-)-alpha-pinene + diphosphate products are (-)-alpha-pinene and (-)-beta-pinene, in a ratio of 6:94 ? 418647 4.2.3.119 geranyl diphosphate - Picea sitchensis (-)-alpha-pinene + diphosphate products are (-)-alpha-pinene and (-)-beta-pinene, in a ratio of about 35:10 ? 418647 4.2.3.119 geranyl diphosphate - Salvia officinalis (-)-alpha-pinene + diphosphate products are (-)-alpha-pinene, (-)-beta-pinene, and (-)-camphene ? 418647 4.2.3.119 geranyl diphosphate - Salvia officinalis (-)-alpha-pinene + diphosphate products are (-)-camphene and (-)alpha-pinene ? 418647 4.2.3.119 geranyl diphosphate - Salvia officinalis (-)-alpha-pinene + diphosphate products are (-)-camphene, (-)-alpha-pinene, (-)-beta-pinene, (-)-limonene and myrcene ? 418647 4.2.3.119 geranyl diphosphate - Abies grandis (-)-alpha-pinene + diphosphate products are 20% (-)-alpha-pinene, 6% (-)-beta-pinene, 26% (-)-limonene, 37% (-)-9-beta-phellandrene, and about 11% other monoterpenes ? 418647 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 ? 418647 4.2.3.119 geranyl diphosphate - Abies grandis (-)-alpha-pinene + diphosphate products are 29% (-)-alpha-pinene, 63% (-)-beta-pinene, 1.8% myrcene, 3.6% limonene ? 418647 4.2.3.119 geranyl diphosphate - Abies grandis (-)-alpha-pinene + diphosphate products are 31.9% (-)-alpha-pinene and 63.9% (-)-beta-pinene, plus 4.2% myrcene ? 418647 4.2.3.119 geranyl diphosphate - Abies grandis (-)-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 ? 418647 4.2.3.119 geranyl diphosphate - Pinus taeda (-)-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 ? 418647 4.2.3.119 geranyl diphosphate - Salvia officinalis (-)-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 ? 418647 4.2.3.119 geranyl diphosphate - Pinus banksiana (-)-alpha-pinene + diphosphate 75.2% (-)-beta-pinene + 13.1% (-)-alpha-pinene ? 418647 4.2.3.119 geranyl diphosphate - Pinus contorta (-)-alpha-pinene + diphosphate 76.6% (-)-alpha-pinene + 9.9% (-)-beta-pinene ? 418647 4.2.3.119 geranyl diphosphate - Pinus banksiana (-)-alpha-pinene + diphosphate 77.9% (-)-alpha-pinene + 9.6% (-)-beta-pinene ? 418647 4.2.3.119 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 Salvia officinalis ? - ? 89 4.2.3.119 additional information entire product set is derived in stereochemically consistent fashion via (-)-3S-linalyl diphosphate as intermediate Abies grandis ? - ? 89 4.2.3.119 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 Salvia officinalis ? - ? 89 4.2.3.119 additional information no substrates: farnesyl diphosphate, geranygeranyl diphosphate Pseudotsuga menziesii ? - ? 89 4.2.3.119 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 Salvia officinalis ? - ? 89 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 ? - ? 89 4.2.3.119 additional information substrates geranyl, neryl, and (3S)-linalyl diphosphate yield exclusively the (-)-isomer series, whereas (3R)-linalyl diphosphate affords the (+)-isomers at low rates Salvia officinalis ? - ? 89 4.2.3.119 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 Wurfbainia villosa ? - ? 89 4.2.3.119 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 Paeonia lactiflora ? - ? 89 4.2.3.119 neryl diphosphate - Salvia officinalis (-)-alpha-pinene + diphosphate products are (-)-alpha-pinene, (-)-beta-pinene, and (-)-camphene ? 418948 4.2.3.119 neryl diphosphate - Salvia officinalis (-)-alpha-pinene + diphosphate products are (-)-camphene and (-)alpha-pinene ? 418948 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 ? 418948