Farnesyl pyrophosphate

Farnesyl pyrophosphate
Names
IUPAC name
(2E,6E)-3,7,11-Trimethyldodeca-2,6,10-triene-1-pyrophosphate
Identifiers
13058-04-3 YesY
ChemSpider 393270 N
MeSH farnesyl+pyrophosphate
PubChem 706
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 verify (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).

Biosynthesis

Farnesyl pyrophosphate synthase (a prenyl transferase) [1] 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:

Pharmacology

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

  1. Kulkarni RS, Pandit SS, Chidley HG, Nagel R, Schmidt A, Gershenzon J, Pujari KH, Giri AP and Gupta VS, 2013, Characterization of three novel isoprenyl diphosphate synthases from the terpenoid rich mango fruit. Plant Physiology and Biochemistry, 71, 121–131.
This article is issued from Wikipedia - version of the Thursday, April 28, 2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.