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Geranylgeranyl pyrophosphate

From Wikipedia, the free encyclopedia
Geranylgeranyl pyrophosphate
Names
Preferred IUPAC name
(2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-yl trihydrogen diphosphate
Other names
geranylgeranyl diphosphate
trans-geranylgeranyl diphosphate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSHgeranylgeranyl+pyrophosphate
UNII
  • InChI=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+ checkY
    Key: OINNEUNVOZHBOX-QIRCYJPOSA-N checkY
  • 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+
    Key: OINNEUNVOZHBOX-QIRCYJPOBR
  • O=P(O)(O)OP(=O)(O)OC/C=C(/CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C)C
Properties
C20H36O7P2
Molar mass450.449 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Geranylgeranyl pyrophosphate is an intermediate in the biosynthesis ofditerpenes and diterpenoids.[1] It is also the precursor tocarotenoids,gibberellins,tocopherols, andchlorophylls.

It is also a precursor togeranylgeranylated proteins, which is its primary use in human cells.[2]

It is formed fromfarnesyl pyrophosphate by the addition of anisoprene unit fromisopentenyl pyrophosphate.

InDrosophila, geranylgeranyl pyrophosphate is synthesised by HMG-CoA encoded by the Columbus gene. Geranylgeranyl pyrophosphate is utilised as a chemoattractant for migratinggerm cells that have traversed themidgutepithelia. The attractant signal is produced at thegonadal precursors, directing the germ cells to these sites, where they will differentiate into eggs andspermatozoa (sperm).

Related compounds

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References

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  1. ^Davis, Edward M.; Croteau, Rodney (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.
  2. ^Wiemer, AJ; Wiemer, DF; Hohl, RJ (December 2011). "Geranylgeranyl diphosphate synthase: an emerging therapeutic target".Clinical Pharmacology and Therapeutics.90 (6):804–12.doi:10.1038/clpt.2011.215.PMID 22048229.S2CID 27913789.
Mevalonate pathway
toHMG-CoA
Ketone bodies
toDMAPP
Geranyl-
Carotenoid
Non-mevalonate pathway
ToCholesterol
FromCholesterol
toSteroid hormones
Nonhuman
ToSitosterol
ToErgocalciferol
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