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Literature summary extracted from

  • LaFever, R.E.; Croteau, R.
    Hydride shifts in the biosynthesis of the p-menthane monoterpenes alpha-terpinene, gamma-terpinene, and beta-phellandrene (1993), Arch. Biochem. Biophys., 301, 361-366.
    View publication on PubMed

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
4.2.3.115 soluble
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Dysphania ambrosioides
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-

Organism

EC Number Organism UniProt Comment Textmining
4.2.3.52 Pinus contorta
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Douglas var. latifolia Engelman
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4.2.3.114 Thymus vulgaris
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-
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4.2.3.115 Dysphania ambrosioides
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-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
4.2.3.52 geranyl diphosphate = (4S)-beta-phellandrene + diphosphate a 1,3-hydride shift from C3 to C8 of the cyclohexene nucleus is involved in the formation of phellandrene Pinus contorta
4.2.3.114 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
4.2.3.115 geranyl diphosphate = alpha-terpinene + diphosphate the isomerization-cyclization involves a 1,2-hydride shift in the terpinyl cation to the terpin-4-yl-cation Dysphania ambrosioides

Source Tissue

EC Number Source Tissue Comment Organism Textmining
4.2.3.52 stem
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Pinus contorta
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Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.3.52 geranyl diphosphate a 1,3-hydride shift from C3 to C8 of the cyclohexene nucleus is involved in the formation of phellandrene Pinus contorta (4S)-beta-phellandrene + 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 ?
4.2.3.115 geranyl diphosphate
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Dysphania ambrosioides alpha-terpinene + diphosphate the isomerization-cyclization involves a 1,2-hydride shift in the terpinyl cation to the terpin-4-yl-cation ?

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
4.2.3.115 6.4
-
-
Dysphania ambrosioides