Geranylgeranyl pyrophosphate

Geranylgeranyl pyrophosphate
Names
	IUPAC name (2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraene-1-pyrophosphate
Identifiers
CAS Number	6699-20-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:48861 ;
ChemSpider	394418 ;
IUPHAR/BPS	3052;
MeSH	geranylgeranyl+pyrophosphate
PubChem CID	447277;
UNII	N21T0D88LX ;
	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+ Key: OINNEUNVOZHBOX-QIRCYJPOSA-N ; 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	450.449 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

^ 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.

[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.

[1]

[2]

Names

IUPAC name (2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraene-1-pyrophosphate
Identifiers
CAS Number	6699-20-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:48861
ChemSpider	394418
IUPHAR/BPS	3052
MeSH	geranylgeranyl+pyrophosphate
PubChem CID	447277
UNII	N21T0D88LX
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+ Key: OINNEUNVOZHBOX-QIRCYJPOSA-N 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	450.449 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).