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Literature summary for 4.2.3.114 extracted from
- Hydride shifts in the biosynthesis of the p-menthane monoterpenes alpha-terpinene, gamma-terpinene, and beta-phellandrene (1993), Arch. Biochem. Biophys., 301, 361-366.
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Thymus vulgaris | - |
- |
- |
Reaction
| Reaction | Comment | Organism | Reaction ID |
|---|---|---|---|
| geranyl diphosphate = 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 | Thymus vulgaris |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| 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 | ? |  |
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