View source for Chemistry:Geranylgeranyl pyrophosphate

{{Chembox
|Watchedfields = changed
|verifiedrevid = 443835762
|ImageFile = Geranylgeranyl pyrophosphate skeletal.svg
|ImageSize = 250px
|PIN = (2''E'',6''E'',10''E'')-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-yl trihydrogen diphosphate
| OtherNames = geranylgeranyl diphosphate<br />''trans''-geranylgeranyl diphosphate
|Section1={{Chembox Identifiers
|IUPHAR_ligand = 3052
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 394418
|InChI = 1/C20H36O7P2/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-26-29(24,25)27-28(21,22)23/h9,11,13,15H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H2,21,22,23)/b18-11+,19-13+,20-15+
|InChIKey = OINNEUNVOZHBOX-QIRCYJPOBR
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C20H36O7P2/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-26-29(24,25)27-28(21,22)23/h9,11,13,15H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H2,21,22,23)/b18-11+,19-13+,20-15+
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = OINNEUNVOZHBOX-QIRCYJPOSA-N
|CASNo_Ref = {{cascite|correct|??}}
|CASNo = 6699-20-3
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = N21T0D88LX
|PubChem = 447277
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 48861
|SMILES = O=P(O)(O)OP(=O)(O)OC/C=C(/CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C)C
|MeSHName = geranylgeranyl+pyrophosphate
 }}
|Section2={{Chembox Properties
|C=20 | H=36 | O=7 | P=2 
 }}
}}

'''Geranylgeranyl pyrophosphate''' is an intermediate in the biosynthesis of [[Chemistry:Diterpene|diterpene]]s and di[[Biology:Terpenoid|terpenoid]]s.<ref>{{cite journal|title=Cyclization enzymes in the biosynthesis of monoterpenes, sesquiterpenes, and diterpenes|author1=Davis, Edward M. |author2=Croteau, Rodney |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 the precursor to [[Biology:Carotenoid|carotenoid]]s, [[Earth:Gibberellin|gibberellin]]s, [[Chemistry:Tocopherol|tocopherol]]s, and [[Biology:Chlorophyll|chlorophyll]]s.

It is also a precursor to [[Biology:Geranylgeranylation|geranylgeranylated]] proteins, which is its primary use in human cells.<ref>{{cite journal|last1=Wiemer|first1=AJ|last2=Wiemer|first2=DF|last3=Hohl|first3=RJ|title=Geranylgeranyl diphosphate synthase: an emerging therapeutic target.|journal=Clinical Pharmacology and Therapeutics|date=December 2011|volume=90|issue=6|pages=804–12|pmid=22048229|doi=10.1038/clpt.2011.215|s2cid=27913789}}</ref>

It is formed from [[Chemistry:Farnesyl pyrophosphate|farnesyl pyrophosphate]] by the addition of an [[Chemistry:Isoprene|isoprene]] unit from [[Chemistry:Isopentenyl pyrophosphate|isopentenyl pyrophosphate]].

In ''[[Biology:Drosophila|Drosophila]]'', geranylgeranyl pyrophosphate is synthesised by HMG-CoA encoded by the Columbus gene. Geranylgeranyl pyrophosphate is utilised as a chemoattractant for migrating [[Biology:Germ cell|germ cell]]s that have traversed the midgut epithelia. The attractant signal is produced at the gonadal precursors, directing the germ cells to these sites, where they will differentiate into eggs and spermatozoa (sperm).

==Related compounds==
* [[Chemistry:Farnesyl pyrophosphate|Farnesyl pyrophosphate]]
* [[Chemistry:Geranylgeraniol|Geranylgeraniol]]
* [[Chemistry:Geranyl pyrophosphate|Geranyl pyrophosphate]]

==References==
{{reflist}}

{{Cholesterol metabolism intermediates}}

{{DEFAULTSORT:Geranylgeranyl Pyrophosphate}}
[[Category:Organophosphates]]
[[Category:Diterpenes]]


{{Sourceattribution|Geranylgeranyl pyrophosphate}}