EC Number |
Substrates |
Organism |
Products |
Reversibility |
---|
4.2.3.114 | geranyl diphosphate |
- |
Oryza sativa |
gamma-terpinene + diphosphate |
- |
? |
4.2.3.114 | geranyl diphosphate |
- |
Origanum majorana |
gamma-terpinene + diphosphate |
- |
? |
4.2.3.114 | geranyl diphosphate |
- |
Thymus vulgaris |
gamma-terpinene + diphosphate |
- |
? |
4.2.3.114 | geranyl diphosphate |
- |
Origanum vulgare |
gamma-terpinene + diphosphate |
- |
? |
4.2.3.114 | geranyl diphosphate |
- |
Citrus unshiu |
gamma-terpinene + diphosphate |
- |
? |
4.2.3.114 | geranyl diphosphate |
- |
Thymus vulgaris |
gamma-terpinene + diphosphate |
ionization of geranyl diphosphate folded in left-handed helical form gives, by syn-isomerization, (3R)-linalyl diphosphate, which by rotation about C2-C3 provides the cisoid, anti-endo conformation. Ionization and cyclization of this bound intermediate yield the (4R)-alpha-terpinyl cation that, following the 1,2-hydride shift, affords the terpinen-4-yl cation. Loss of the (5S)-proton terminates the reaction to generate gamma-terpinene |
? |
4.2.3.114 | geranyl diphosphate |
- |
Citrus unshiu |
gamma-terpinene + diphosphate |
plus small amounts of alpha-pinene, limonene |
? |
4.2.3.114 | geranyl diphosphate |
- |
Citrus limon |
gamma-terpinene + diphosphate |
products are 71.4% gamma-terpinene, with lower amounts of limonene (9.1%), alpha-pinene (5.6%), beta-pinene (4.7%), alpha-terpinolene (3.7%), alpha-thujene (2.5%), alpha-terpinene (1.7%), myrcene (0.9%), sabinene (0.4%) and a trace of p-cymene |
? |
4.2.3.114 | geranyl diphosphate |
- |
Origanum vulgare |
gamma-terpinene + diphosphate |
products are 80% gamma-terpinene and the minor products, alpha-thujene (7.2%), alpha-terpinene (6%), myrcene (2.6%), sabinene (1.3%), (+)-R-limonene (1.2%), alpha-pinene (1%) and alpha-phellandrene (0.8%), as well as trace amounts of p-cymene and beta-pinene |
? |
4.2.3.114 | geranyl diphosphate |
- |
Thymus vulgaris |
gamma-terpinene + diphosphate |
products are about 64% gamma-terpinen, 10% alpha-thujene, 4% myrcene, 4% alpha-terpinene, 2% limonene, 3% linalool, 2% terpinen-4-ol, 3% alpha-terpineol |
? |