Geranylgeranyl pyrophosphate

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
CAS Number
  • 6699-20-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:48861 checkY
ChemSpider
  • 394418 checkY
IUPHAR/BPS
  • 3052
MeSH geranylgeranyl+pyrophosphate
PubChem CID
  • 447277
UNII
  • N21T0D88LX checkY
CompTox Dashboard (EPA)
  • DTXSID90863929 Edit this at Wikidata
InChI
  • 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
Chemical formula
 C20H36O7P2
Molar mass 450.449 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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Infobox references
Chemical compound

Geranylgeranyl pyrophosphate is an intermediate in the biosynthesis of diterpenes and diterpenoids.[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.[2]

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).

Related compounds

References

  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.
  • v
  • t
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Mevalonate pathway
to HMG-CoA
Ketone bodies
to DMAPP
Geranyl-
Carotenoid
Non-mevalonate pathway
To CholesterolFrom Cholesterol
to Steroid hormones
  • 22R-Hydroxycholesterol
  • 20α,22R-Dihydroxycholesterol
  • See here instead.
Nonhuman
To Sitosterol
To Ergocalciferol
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