Geranylgeranyl pyrophosphate is an intermediate in the biosynthesis of diterpenes and diterpenoids.[1] It is also the precursor to carotenoids, gibberellins, tocopherols, and chlorophylls.
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| 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)
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| ChemSpider | |
| MeSH | geranylgeranyl+pyrophosphate |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| 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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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
editReferences
edit- ^ 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.
- ^ 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.