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Farnesyl pyrophosphate

In today's world, Farnesyl pyrophosphate is a topic that has become relevant in different areas of society. From its impact on people's daily lives to its influence on the economy and politics, Farnesyl pyrophosphate has become a fundamental element to take into account today. Over the years, Farnesyl pyrophosphate has generated debates, controversies and different positions that have marked the way we perceive it and relate to it. In this article, we will delve into the different aspects surrounding Farnesyl pyrophosphate, from its origin to its impact on today's society, analyzing its importance and the implications it has on our daily lives.

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Farnesyl pyrophosphate
Skeletal formula
Skeletal formula
Ball-and-stick model
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
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 , 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).

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:

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. Bibcode:2013PlPB...71..121K. 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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