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Literature summary extracted from

  • Croteau, R.; Felton, N.M.; Wheeler, C.J.
    Stereochemistry at C-1 of geranyl pyrophosphate and neryl pyrophosphate in the cyclization to (+)- and (-)-bornyl pyrophosphate (1985), J. Biol. Chem., 260, 5956-5962.
    View publication on PubMed

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
5.5.1.22 geranyl diphosphate Salvia officinalis
-
 (-)-bornyl diphosphate i.e. (2R,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl diphosphate ?
5.5.1.22 geranyl diphosphate Tanacetum vulgare
-
 (-)-bornyl diphosphate i.e. (2R,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl diphosphate ?

Organism

EC Number Organism UniProt Comment Textmining
5.5.1.8 Salvia officinalis
-
-
-
5.5.1.8 Tanacetum vulgare
-
-
-
5.5.1.22 Salvia officinalis
-
-
-
5.5.1.22 Tanacetum vulgare
-
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
5.5.1.8 geranyl diphosphate = (+)-bornyl diphosphate mechanism Salvia officinalis
a
5.5.1.8 geranyl diphosphate = (+)-bornyl diphosphate mechanism Tanacetum vulgare
a
5.5.1.8 geranyl diphosphate = (+)-bornyl diphosphate geranyl diphosphate is first stereospecifically isomerized to linalyl diphosphate which, following rotation about C-2-B-3 to the cisoid conformer, cyclizes from the anti-endo configuration. Neryl diphosphate cyclizes either directly or via the linalyl intermediate without the attendant rotation Salvia officinalis
a
5.5.1.8 geranyl diphosphate = (+)-bornyl diphosphate geranyl diphosphate is first stereospecifically isomerized to linalyl diphosphate which, following rotation about C-2-B-3 to the cisoid conformer, cyclizes from the anti-endo configuration. Neryl diphosphate cyclizes either directly or via the linalyl intermediate without the attendant rotation Tanacetum vulgare
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
5.5.1.8 Geranyl diphosphate
-
 Salvia officinalis (+)-Bornyl-diphosphate
-
 ?
5.5.1.8 Geranyl diphosphate
-
 Tanacetum vulgare (-)-Bornyl-diphosphate
-
 ?
5.5.1.22 geranyl diphosphate
-
 Salvia officinalis (-)-bornyl diphosphate i.e. (2R,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl diphosphate ?
5.5.1.22 geranyl diphosphate
-
 Tanacetum vulgare (-)-bornyl diphosphate i.e. (2R,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl diphosphate ?
5.5.1.22 geranyl diphosphate reaction mechanism whereby geranyl diphosphate is first stereospecifically isomerized to linalyl diophosphate which, following rotation about C-2-C-3 to the cisoid conformer, cyclizes from the anti-endo configuration Salvia officinalis (-)-bornyl diphosphate i.e. (2R,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl diphosphate ?
5.5.1.22 geranyl diphosphate reaction mechanism whereby geranyl diphosphate is first stereospecifically isomerized to linalyl pyrophosphawte which, following rotation about C-2-C-3 to the cisoid conformer, cyclizes from the anti-endo configuration Tanacetum vulgare (-)-bornyl diphosphate i.e. (2R,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl diphosphate ?
5.5.1.22 neryl diphosphate neryl diphosphate cyclizes either directly or via the linalyl intermediate without the attendant rotation Salvia officinalis (-)-bornyl diphosphate
-
 ?
5.5.1.22 neryl diphosphate neryl pyrophosphate cyclizes either directly or via the linalyl intermediate without the attendant rotation Tanacetum vulgare (-)-bornyl diphosphate
-
 ?