Farnesyl pyrophosphate

Farnesyl pyrophosphate
Skeletal formula
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 [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 thousand of compounds.[1] These 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. 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.