farnesyl pyrophosphate
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 424660305
| ImageFile = Farnesylpyrophosphat Strukturformel V2a.svg
| ImageSize = 220px
| ImageName = Skeletal formula
| ImageFile1 = Farnesyl-pyrophosphate-3D-balls.png
| ImageSize1 = 250px
| ImageName1 = Ball-and-stick model
| PIN = (2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-yl trihydrogen diphosphate
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo= 372-97-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = G8X8WT527W
| PubChem=445713
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 393270
| SMILES=CC(=CCC/C(=C/CC/C(=C/COP(=O)(O)OP(=O)(O)O)/C)/C)C
| 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+
| InChIKey=VWFJDQUYCIWHTN-YFVJMOTDSA-N
| MeSHName=farnesyl+pyrophosphate
}}
|Section2={{Chembox Properties
| C=15 | H=28 | O=7 | P=2
}}
}}
Farnesyl pyrophosphate (FPP), also known as farnesyl diphosphate (FDP), is the precursor to all sesquiterpenes, which comprises thousand of compounds.{{cite book |doi=10.1002/0471238961.2005181602120504.a01.pub2|chapter=Terpenoids |title=Kirk-Othmer Encyclopedia of Chemical Technology |year=2006 |last1=Sell |first1=Charles S. |isbn=0471238961 }} These include all sesquiterpenes as well as sterols and carotenoids.{{cite journal|title=Cyclization enzymes in the biosynthesis of monoterpenes, sesquiterpenes, and diterpenes| vauthors = Davis EM, Croteau R |s2cid=53419212|journal=Topics in Current Chemistry |year=2000 |volume=209 |pages=53–95 |doi=10.1007/3-540-48146-X_2 |isbn=978-3-540-66573-1}} 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){{cite journal | vauthors = Kulkarni RS, Pandit SS, Chidley HG, Nagel R, Schmidt A, Gershenzon J, Pujari KH, Giri AP, Gupta VS | display-authors = 6 |title=Characterization of three novel isoprenyl diphosphate synthases from the terpenoid rich mango fruit |journal=Plant Physiology and Biochemistry |date=October 2013 |volume=71 |pages=121–131 |doi=10.1016/j.plaphy.2013.07.006| pmid = 23911730 }} catalyzes sequential condensation reactions of dimethylallyl pyrophosphate with 2 units of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate:
:File:FarnesolPPbiosyn.svg{{clear-left}}
Pharmacology
The above reactions are inhibited by bisphosphonates (used for osteoporosis).{{cite journal | vauthors = Russell RG | title = Bisphosphonates: from bench to bedside | journal = Annals of the New York Academy of Sciences | volume = 1068 | issue = April 2006 | pages = 367–401 | date = April 2006 | pmid = 16831938 | doi = 10.1196/annals.1346.041 | s2cid = 20706956 | bibcode = 2006NYASA1068..367R }} Farnesyl pyrophosphate is a selective agonist of TRPV3.{{cite journal | vauthors = Bang S, Yoo S, Yang TJ, Cho H, Hwang SW | title = Farnesyl pyrophosphate is a novel pain-producing molecule via specific activation of TRPV3 | journal = The Journal of Biological Chemistry | volume = 285 | issue = 25 | pages = 19362–71 | date = June 2010 | pmid = 20395302 | pmc = 2885216 | doi = 10.1074/jbc.M109.087742 | doi-access = free }}
Related compounds
References
{{Reflist}}
{{Cholesterol metabolism intermediates}}
{{DEFAULTSORT:Farnesyl Pyrophosphate}}