Geranylgeranyl pyrophosphate

Geranylgeranyl pyrophosphate
Names

IUPAC name (2E,4E,6E)-3,5,7,11-Tetramethyldodeca-2,4,6,10-tetraene-1-pyrrophosphate
Identifiers
CAS Number	6699-20-3^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:48861^Y
ChemSpider	394418^Y
IUPHAR/BPS	3052
MeSH	geranylgeranyl+pyrophosphate
PubChem	447277
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+^Y Key: OINNEUNVOZHBOX-QIRCYJPOSA-N^Y 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
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
Properties
Chemical formula	C₂₀H₃₆O₇P₂
Molar mass	450.45 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

Geranylgeranyl pyrophosphate is an intermediate in the biosynthesis of some terpenes and terpenoids.^[1] In plants 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]

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 ova (eggs) and spermatozoa (sperm).

Related compounds

References

↑ Cholesterol Synthesis, Rensselaer Polytechnic Institute]
↑ 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.

Cholesterol and steroid metabolic intermediates

Mevalonate pathway

to HMG-CoA	Acetyl-CoA Acetoacetyl-CoA HMB HMB-CoA HMG-CoA

Ketone bodies	Acetone Acetoacetic acid β-Hydroxybutyric acid

to DMAPP	Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate

Geranyl-	Geranyl pyrophosphate Geranylgeranyl pyrophosphate

Carotenoid	Prephytoene diphosphate Phytoene

Non-mevalonate pathway

To Cholesterol

From Cholesterol
(to steroids)

Steroid hormones

See here instead.

Nonhuman

Phytosterols	Stigmasterol Brassicasterol

Ergosterols	Ergosterol Ergocalciferol

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