Farnesyl pyrophosphate: Difference between revisions
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==Biosynthesis== |
==Biosynthesis== |
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[[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: |
[[Farnesyl pyrophosphate synthase]] (a [[prenyl transferase]]) <ref>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.</ref> 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: |
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* Dimethylallyl pyrophosphate reacts with 3-isopentenyl pyrophosphate to form [[geranyl pyrophosphate]]: |
* Dimethylallyl pyrophosphate reacts with 3-isopentenyl pyrophosphate to form [[geranyl pyrophosphate]]: |
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Revision as of 06:42, 28 April 2016
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| Names | |
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| IUPAC name
(2E,6E)-3,7,11-Trimethyldodeca-2,6,10-triene-1-pyrophosphate
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| Identifiers | |
| ChemSpider | |
| MeSH | farnesyl+pyrophosphate |
PubChem CID
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CompTox Dashboard (EPA)
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| 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).
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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:
- 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) [citation needed].
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
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- ^ 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.