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Literature summary for 5.5.1.22 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
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Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Salvia officinalis
-
-
-
Tanacetum vulgare
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
geranyl diphosphate
-
 Salvia officinalis (-)-bornyl diphosphate i.e. (2R,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl diphosphate ?
geranyl diphosphate
-
 Tanacetum vulgare (-)-bornyl diphosphate i.e. (2R,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl diphosphate ?
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 ?
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 ?
neryl diphosphate neryl diphosphate cyclizes either directly or via the linalyl intermediate without the attendant rotation Salvia officinalis (-)-bornyl diphosphate
-
 ?
neryl diphosphate neryl pyrophosphate cyclizes either directly or via the linalyl intermediate without the attendant rotation Tanacetum vulgare (-)-bornyl diphosphate
-
 ?