Farnesyl pyrophosphate

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Farnesyl pyrophosphate
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 13058-04-3 YesY
PubChem 706
ChemSpider 393270
MeSH farnesyl+pyrophosphate
Properties
Molecular formula C15H28O7P2
Molar mass 382.326
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Farnesyl pyrophosphate (FPP), also known as farnesyl diphosphate (FDP), is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes, terpenoids, and sterols.

It is used in the synthesis of CoQ (part of the electron transport chain), as well as being the immediate precursor of squalene (via the enzyme squalene synthase), dehydrodolichol diphosphate (a precursor of dolichol, which transports proteins to the ER lumen for N-glycosylation), and geranylgeranyl pyrophosphate (GGPP).

Biosynthesis[edit]

Farnesyl pyrophosphate synthase (a prenyl transferase) catalyzes sequential condensation reactions of dimethylallyl pyrophosphate with 2 units of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate, as is shown in the following two steps:

Cholesterol-Synthesis-Reaction8.png

  • Geranyl pyrophosphate then reacts with another molecule of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate

Cholesterol-Synthesis-Reaction9.png

Pharmacology[edit]

The above reactions are inhibited by bisphosphonates (used for osteoporosis).

Statin-induced rhabdomyolysis is due to the depletion of farnesyl-PPi, which leads to a depletion of CoQ in the electron transport chain of mitochondria, an organelle that is found in great numbers in myocytes.

Related compounds[edit]