Farnesyl pyrophosphate

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Farnesyl pyrophosphate
Skeletal formula Farnesylpyrophosphat Strukturformel V2a.svg
Skeletal formula
Ball-and-stick model Farnesyl-pyrophosphate-3D-balls.png
Ball-and-stick model
Names
Preferred IUPAC name
(2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-yl trihydrogen diphosphate
Identifiers
3D model (JSmol)
ChemSpider
MeSH farnesyl+pyrophosphate
PubChem CID
UNII
  • InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+
    Key: VWFJDQUYCIWHTN-YFVJMOTDSA-N
  • CC(=CCC/C(=C/CC/C(=C/COP(=O)(O)OP(=O)(O)O)/C)/C)C
Properties
C15H28O7P2
Molar mass 382.330 g·mol−1
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 the precursor to all sesquiterpenes, which comprises thousands of compounds. [1] These[ clarification needed ] include all sesquiterpenes as well as sterols and carotenoids. [2] It is also used in the synthesis of CoQ (part of the electron transport chain), as well as dehydrodolichol diphosphate (a precursor of dolichol, which transports proteins to the ER lumen for N-glycosylation).

Contents

Biosynthesis

Farnesyl pyrophosphate synthase (a prenyl transferase) [3] catalyzes sequential condensation reactions of dimethylallyl pyrophosphate with 2 units of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate:

FarnesolPPbiosyn.svg

Pharmacology

The above reactions are inhibited by bisphosphonates (used for osteoporosis). [4] Farnesyl pyrophosphate is a selective agonist of TRPV3. [5]

References

  1. ↑ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN   0471238961.
  2. ↑ Davis EM, Croteau R (2000). "Cyclization enzymes in the biosynthesis of monoterpenes, sesquiterpenes, and diterpenes". Topics in Current Chemistry. 209: 53–95. doi:10.1007/3-540-48146-X_2. ISBN   978-3-540-66573-1. S2CID   53419212.
  3. ↑ Kulkarni RS, Pandit SS, Chidley HG, Nagel R, Schmidt A, Gershenzon J, et al. (October 2013). "Characterization of three novel isoprenyl diphosphate synthases from the terpenoid rich mango fruit". Plant Physiology and Biochemistry. 71: 121–131. doi:10.1016/j.plaphy.2013.07.006. PMID   23911730.
  4. ↑ Russell RG (April 2006). "Bisphosphonates: from bench to bedside". Annals of the New York Academy of Sciences. 1068 (April 2006): 367–401. Bibcode:2006NYASA1068..367R. doi:10.1196/annals.1346.041. PMID   16831938. S2CID   20706956.
  5. ↑ Bang S, Yoo S, Yang TJ, Cho H, Hwang SW (June 2010). "Farnesyl pyrophosphate is a novel pain-producing molecule via specific activation of TRPV3". The Journal of Biological Chemistry. 285 (25): 19362–71. doi: 10.1074/jbc.M109.087742 . PMC   2885216 . PMID   20395302.
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