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Farnesyl pyrophosphate

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Formula
  
C15H28O7P2

Molar mass
  
382.3261 g/mol

Farnesyl pyrophosphate Farnesyl pyrophosphate Wikipedia

Human farnesyl pyrophosphate synthase allosteric product inhibition


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.

Contents

Farnesyl pyrophosphate FARNESYL PYROPHOSPHATE CAS 13058043 02159919 MP Biomedicals

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 Product Details for Farnesyl Diphosphate FPP 104715197

Human farnesyl pyrophosphate synthase the full catalytic cycle


Biosynthesis

Farnesyl pyrophosphate wwwchemspidercomImagesHandlerashxid393270ampw

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:

  • Dimethylallyl pyrophosphate reacts with 3-isopentenyl pyrophosphate to form geranyl pyrophosphate:
  • Geranyl pyrophosphate then reacts with another molecule of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate
  • Pharmacology

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

    Farnesyl pyrophosphate FileFarnesyl pyrophosphatesvg Wikimedia Commons

    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.

  • Farnesene
  • Farnesol
  • Geranyl pyrophosphate
  • Geranylgeranyl pyrophosphate
  • References

    Farnesyl pyrophosphate Wikipedia