Farnesyl pyrophosphate: Difference between revisions

{{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 = (2''E'',6''E'')-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

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'''Farnesyl pyrophosphate''' ('''FPP'''), also known as '''farnesyl diphosphate''' ('''FDP'''), is an intermediate in the biosynthesis of [[terpene]]s and [[terpenoid]]s such as [[Sterol|sterols]] and [[Carotenoid|carotenoids]].<ref>{{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}}</ref> 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|''N''-glycosylation]]).

[[Farnesyl pyrophosphate synthase]] (a [[prenyl transferase]])<ref>{{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 }}</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:

:[[Image:Cholesterol-Synthesis-Reaction8.png|600px|left]]{{clear-left}}

* Geranyl pyrophosphate then reacts with another molecule of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate

:[[Image:Cholesterol-Synthesis-Reaction9.png|600px|left]]{{clear-left}}

==Pharmacology==

The above reactions are inhibited by [[bisphosphonate]]s (used for [[osteoporosis]]).<ref>{{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 }}</ref> Farnesyl pyrophosphate is a [[selective agonist]] of [[TRPV3]].<ref name="pmid20395302">{{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 }}</ref>

*[[Geranyl pyrophosphate]]

*[[Geranylgeranyl pyrophosphate]]

== References ==

{{Reflist}}

{{Cholesterol metabolism intermediates}}

{{DEFAULTSORT:Farnesyl Pyrophosphate}}

[[Category:Pyrophosphate esters]]

[[Category:Sesquiterpenes]]