Farnesyl pyrophosphate: Difference between revisions
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| ImageFile = Farnesylpyrophosphat Strukturformel V2a.svg |
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| PIN = (2''E'',6''E'')-3,7,11-Trimethyldodeca-2,6,10-trien-1-yl trihydrogen diphosphate |
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| Formula=C<sub>15</sub>H<sub>28</sub>O<sub>7</sub>P<sub>2</sub> |
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| MolarMass=382.326 |
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| UNII = G8X8WT527W |
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| SMILES=CC(=CCC/C(=C/CC/C(=C/COP(=O)(O)OP(=O)(O)O)/C)/C)C |
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| 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+ |
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| C=15 | H=28 | O=7 | P=2 |
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'''Farnesyl pyrophosphate''' (FPP) is an intermediate in the [[HMG-CoA reductase pathway]] used by organisms in the biosynthesis of [[terpene]]s and [[terpenoid]]s. |
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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]]). |
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It is the immediate precursor of [[squalene]] (via the enzyme [[squalene synthase]]), dehydrodolichol diphosphate (a precursor of [[dolichol]]), and geranylgeranyl pyrophoshate (GGPP). |
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==Biosynthesis== |
==Biosynthesis== |
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[[Farnesyl pyrophosphate synthase]] (a [[prenyl transferase]]) catalyzes sequential condensation reactions of [[dimethylallyl pyrophosphate]] with 2 units of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate |
[[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: |
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* Dimethylallyl pyrophosphate reacts with 3-isopentenyl pyrophosphate to form [[geranyl pyrophosphate]]: |
* Dimethylallyl pyrophosphate reacts with 3-isopentenyl pyrophosphate to form [[geranyl pyrophosphate]]: |
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[[Image:Cholesterol-Synthesis-Reaction8.png]] |
:[[Image:Cholesterol-Synthesis-Reaction8.png|600px|left]]{{clear-left}} |
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* Geranyl pyrophosphate |
* Geranyl pyrophosphate then reacts with another molecule of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate |
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[[Image:Cholesterol-Synthesis-Reaction9.png]] |
:[[Image:Cholesterol-Synthesis-Reaction9.png|600px|left]]{{clear-left}} |
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== |
==Pharmacology== |
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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> |
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The above reactions are inhibited by [[bisphosphonate]]s (used for [[osteoporosis]]). |
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==Related compounds== |
==Related compounds== |
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*[[Geranyl pyrophosphate]] |
*[[Geranyl pyrophosphate]] |
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*[[Geranylgeranyl pyrophosphate]] |
*[[Geranylgeranyl pyrophosphate]] |
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== References == |
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{{Reflist}} |
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{{Cholesterol metabolism intermediates}} |
{{Cholesterol metabolism intermediates}} |
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{{DEFAULTSORT:Farnesyl Pyrophosphate}} |
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[[Category:Organophosphates]] |
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[[Category: |
[[Category:Pyrophosphate esters]] |
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[[Category: |
[[Category:Sesquiterpenes]] |
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{{biochem-stub}} |
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[[fi:Farnesyylipyrofosfaatti]] |
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Latest revision as of 12:44, 17 July 2024
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| Names | |
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| Preferred IUPAC name
(2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-yl trihydrogen diphosphate | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| MeSH | farnesyl+pyrophosphate |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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 an intermediate in the biosynthesis of terpenes and terpenoids such as sterols and carotenoids.[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
[edit]Farnesyl pyrophosphate synthase (a prenyl transferase)[2] 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:
- Dimethylallyl pyrophosphate reacts with 3-isopentenyl pyrophosphate to form geranyl pyrophosphate:
- Geranyl pyrophosphate then reacts with another molecule of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate
Pharmacology
[edit]The above reactions are inhibited by bisphosphonates (used for osteoporosis).[3] Farnesyl pyrophosphate is a selective agonist of TRPV3.[4]
Related compounds
[edit]References
[edit]- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.