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Farnesyl diphosphate

Farnesyl pyrophosphate
Skeletal formula
Ball-and-stick model
Names
IUPAC name
(2E,6E)-3,7,11-Trimethyldodeca-2,6,10-triene-1-pyrophosphate
Identifiers
ChemSpider
MeSH farnesyl+pyrophosphate
PubChem CID
Properties
C15H28O7P2
Molar mass 382.326
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Farnesyl pyrophosphate (FPP), also known as farnesyl diphosphate (FDP), is an intermediate in both the mevalonate and non-mevalonate pathways 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).

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

Cholesterol-Synthesis-Reaction9.png

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.


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