Geranyl pyrophosphate

The product of this reaction is geranyl pyrophosphate Hydrolysis of the pyrophosphate ester group gives geramol a naturally occurring monoterpene found m rose oil... 

Geranyl pyrophosphate is an allylic pyrophosphate and like dimethylallyl pyrophosphate can act as an alkylating agent toward a molecule of isopentenyl pyrophosphate A 15 carbon carbocation is formed which on deprotonation gives/ar nesyl pyrophosphate... 

The enzyme catalyzed reactions that lead to geraniol and farnesol (as their pyrophosphate esters) are mechanistically related to the acid catalyzed dimerization of alkenes discussed m Section 6 21 The reaction of an allylic pyrophosphate or a carbo cation with a source of rr electrons is a recurring theme m terpene biosynthesis and is invoked to explain the origin of more complicated structural types Consider for exam pie the formation of cyclic monoterpenes Neryl pyrophosphate formed by an enzyme catalyzed isomerization of the E double bond m geranyl pyrophosphate has the proper geometry to form a six membered ring via intramolecular attack of the double bond on the allylic pyrophosphate unit... 

Introduction of Nitrogen into a Terpenoid Skeleton. The acetate-derived fragments (35) mevalonic acid (30), which yields isopentenyl pyrophosphate (31) and its isomer, 3,3-dimethyl ally pyrophosphate (32) a dimeric C -fragment, geranyl pyrophosphate (33), which gives rise to the iridoid loganin (34) and the trimer famesyl pyrophosphate (35), which is also considered the precursor to C q steroids, have already been mentioned (see Table 3... 

Geranyl pyrophosphate [763-10-0 (NH4 salt)] M 314.2, pKeski)-<2, pKesi(2) <2, pKesK3)-3.95, PKesi(4) 6.26. Purified by paper chromatography on Whatman No 3 MM paper in a system of isopropyl aleohol/isobulyl aleohol/ammonia/waler (40 20 1 39), Rp 0.77-0.82. Stored in the dark as the ammonium salt at 0°. 

Prenyl transferase, which catalyses the addition of an allylic pyrophosphate to iso-pentenyl pyrophosphate, also catalyses the hydrolysis of geranyl pyrophosphate.104 Inorganic pyrophosphate stimulates this hydrolysis, and the C—O bond is broken in... 

It is well known that the steroid hormones in mammals are biosynthesized from cholesterol. This compound is derived from the acetate-mevalonate pathway through the monoterpene geranyl pyrophosphate, which undergoes several enzymatic reactions to form the triterpene squalene. 

Croteau, R. B. In Flavor Precursors Teranishi, R. Takeoka, G. R. Guntert, M., Eds. Monoterpene Biosynthesis cyclization of geranyl pyrophosphate to (+)-sabinene Amercian Chemicd Society Symposium Seriers 490 Washington, DC, 1991, pp. 8-20. 

Isopentyl pyrophosphate Geranyl pyrophosphate Carotenoids ---Farnesyl pyrophosphate ... 

Geranyl pyrophosphate [763-10-0] M 314.2. Purified by paper chromatography on Whatman No 3... 

Stage (J) Condensation of Six Activated Isoprene Units to Form Squalene Isopentenyl pyrophosphate and dimethylallyl pyrophosphate now undergo a head-to-tail condensation, in which one pyrophosphate group is displaced and a 10-carbon chain, geranyl pyrophosphate, is formed (Fig. 21-36). (The head is the end to which pyrophosphate is joined.) Geranyl pyrophosphate undergoes another head-to-tail condensation with isopentenyl pyro-... 

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