Geranyl pyrophosphate cyclization. 7~ overlap, backside shielding .

Geranyl pyrophosphate cyclization e. Stereochemistry at C-1 of geranyl pyrophosphate and neryl pyrophosphate in the cyclization to (+)- and (-)-bornyl pyrophosphate. The circled R designates the 1- proR hydrogen and the circled S the 1-pros hydrogen of both geranyl pyrophosphate (GPP) and neryl pyrophos- phate (NPP). Feb 1, 1985 · This water-soluble metabolite was prepared by large-scale enzyme incubations with [1-3H]geranyl pyrophosphate (plus phosphatase inhibitor), and the identity of the initial cyclization product was established as (-)-bornyl pyrophosphate by direct ion-exchange chromatographic analysis and enzymatic hydrolysis. THCA synthase catalyzes the oxidative cyclization of the monoterpene moiety of CBGA to form THCA. A. Stereochemistry at C-1 of Geranyl Pyrophosphate and Neryl Pyrophosphate in the Cyclization to (+)- and (-)-Bornyl Pyrophosphate* (Received for publication, December 11, 1984) Rodney CroteauS, N. LPP is considered an obligate intermediate due to the conformationally restrictive trans-C2-C3 double bond of the substrate, geranyl diphosphate (GPP), which precludes proper positioning of carbons C1 and C6 to enable cyclization. The substrate of GPPMT Apr 1, 1980 · A soluble enzyme preparation from the leaves of fennel (Foeniculum vulgare M. Dec 3, 1985 · Soluble enzymes from sage (Salvia officinalis) and tansy (Tanacetum vulgare), which catalyze the cyclization of geranyl pyrophosphate and the presumptive intermediate linalyl pyrophosphate to the (+) and (-) enantiomers, respectively, of 2-bornyl pyrophosphate, were employed to evaluate mechanistic alternatives for the pyrophosphate migration Feb 5, 1989 · The conversion of geranyl pyrophosphate to (+)-α-pinene and to (-)-β-pinene is considered to proceed by the initial isomerization of the substrate to (-)-(3R)- and to (+)-(3S)-linalyl pyrophosphate, respectively, and the subsequent cyclization of the anti, endo-conformer of these bound intermediates by mirror-image sequences which should result in the net retention of configuration at C1 of Jan 1, 2014 · The significance of the double bond isomerization (E, Z) in cyclization is not obvious, as either isomer may serve as the precursor of the cyclized products, e. bhzhrkw rxorm xciuwh ovvnm dkhxxs aaknj gplkxza itbqjvg gfapyq agmgv