:Geranylgeranyl pyrophosphate

{{Chembox

|Watchedfields = changed

|verifiedrevid = 443835762

|ImageFile = Geranylgeranylpyrophosphat.svg

|ImageSize = 250px

|PIN = (2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-yl trihydrogen diphosphate

| OtherNames = geranylgeranyl diphosphate
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 diterpenes and diterpenoids.{{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}} It is also the precursor to carotenoids, gibberellins, tocopherols, and chlorophylls.

It is also a precursor to geranylgeranylated proteins, which is its primary use in human cells.{{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}}

It is formed from farnesyl pyrophosphate by the addition of an isoprene unit from isopentenyl pyrophosphate.

In Drosophila, geranylgeranyl pyrophosphate is synthesised by HMG-CoA encoded by the Columbus gene. Geranylgeranyl pyrophosphate is utilised as a chemoattractant for migrating germ cells 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).