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{{Chembox
{{Chembox
| Watchedfields = changed
|Watchedfields = changed
| verifiedrevid = 443835762
|verifiedrevid = 443835762
| ImageFile = Geranylgeranyl_pyrophosphate.png
|ImageFile = Geranylgeranylpyrophosphat.svg
| ImageSize =
|ImageSize = 250px
|PIN = (2''E'',6''E'',10''E'')-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-yl trihydrogen diphosphate
| IUPACName =
| OtherNames = geranylgeranyl diphosphate<br />''trans''-geranylgeranyl diphosphate
| OtherNames =
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
|IUPHAR_ligand = 3052
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 394418
|ChemSpiderID = 394418
| 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+
|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+
| InChIKey = OINNEUNVOZHBOX-QIRCYJPOBR
|InChIKey = OINNEUNVOZHBOX-QIRCYJPOBR
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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+
|StdInChI = 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+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OINNEUNVOZHBOX-QIRCYJPOSA-N
|StdInChIKey = OINNEUNVOZHBOX-QIRCYJPOSA-N
⚫
| CASNo = 6699-20-3
⚫
|CASNo_Ref = {{cascite|correct|??}}
⚫
| PubChem = 447277
⚫
|CASNo = 6699-20-3
⚫
| ChEBI_Ref = {{ebicite|correct|EBI}}
|UNII_Ref = {{fdacite|correct|FDA}}
⚫
| ChEBI = 48861
|UNII = N21T0D88LX
⚫
| 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
⚫
|PubChem = 447277
⚫
| MeSHName = geranylgeranyl+pyrophosphate
|ChEBI_Ref = {{ebicite|correct|EBI}}
⚫
}}
⚫
|ChEBI = 48861
⚫
| Section2 = {{Chembox Properties
⚫
|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
| C=20|H=36|O=7|P=2
⚫
|MeSHName = geranylgeranyl+pyrophosphate
| Appearance =
⚫
}}
| Density =
⚫
|Section2={{Chembox Properties
| MeltingPt =
| BoilingPt =
|C=20 | H=36 | O=7 | P=2
}}
}}
| Section3 = {{Chembox Hazards
| Solubility =
| MainHazards =
| FlashPt =
| Autoignition =
}}
}}
}}


'''Geranylgeranyl pyrophosphate''' is an intermediate in the [[HMG-CoA reductase pathway]] used by organisms in the biosynthesis of [[terpene]]s and [[terpenoid]]s.<ref>[http://www.rpi.edu/dept/bcbp/molbiochem/MBWeb/mb2/part1/cholesterol.htm Cholesterol Synthesis], Rensselaer Polytechnic Institute] </ref> In plants it is also the precursor to [[carotenoid]]s, [[gibberellin]]s, [[tocopherol]]s, and [[chlorophyll]]s.
'''Geranylgeranyl pyrophosphate''' is an intermediate in the biosynthesis of [[diterpene]]s and di[[terpenoid]]s.<ref>{{cite journal|title=Cyclization enzymes in the biosynthesis of monoterpenes, sesquiterpenes, and diterpenes|author1=Davis, Edward M. |author2=Croteau, Rodney |journal=Topics in Current Chemistry|year=2000|volume=209|pages=53–95|doi=10.1007/3-540-48146-X_2|isbn=978-3-540-66573-1}}</ref> It is also the precursor to [[carotenoid]]s, [[gibberellin]]s, [[tocopherol]]s, and [[chlorophyll]]s.


It is also a precursor to [[geranylgeranylation|geranylgeranylated]] proteins, which is its primary use in human cells.<ref>{{cite journal|last1=Wiemer|first1=AJ|last2=Wiemer|first2=DF|last3=Hohl|first3=RJ|title=Geranylgeranyl diphosphate synthase: an emerging therapeutic target.|journal=Clinical Pharmacology and Therapeutics|date=December 2011|volume=90|issue=6|pages=804–12|pmid=22048229|doi=10.1038/clpt.2011.215|s2cid=27913789}}</ref>
It is also a precursor to [[geranylgeranylation|geranylgeranylated]] proteins.

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 cell]]s that have traversed the [[midgut]] [[epithelia]]. The attractant signal is produced at the [[gonad]]al precursors, directing the germ cells to these sites, where they will differentiate into eggs and [[spermatozoa]] (sperm).


⚫
In [[Drosophila]], geranylgeranyl pyrophosphate is synthesised by HMG-CoA encoded by the Columbus gene. Geranylgeranyl pyrophosphate is utilised as a chemoattractant for migrating [[germ cell]]s which have traversed the [[midgut]] [[epithelia]]. The attractant signal is produced at the [[gonad]]al precursors, directing the germ cells to these sites, where they will differentiate into [[ova]] (eggs) and [[spermatazoa]] (sperm).
==Related compounds==
==Related compounds==
⚫
* [[Farnesyl pyrophosphate]]
* [[Geranylgeraniol]]
* [[Geranylgeraniol]]
* [[Geranyl pyrophosphate]]
* [[Geranyl pyrophosphate]]
⚫
* [[Farnesyl pyrophosphate]]


==References==
==References==
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{{DEFAULTSORT:Geranylgeranyl Pyrophosphate}}
{{DEFAULTSORT:Geranylgeranyl Pyrophosphate}}
[[Category:Organophosphates]]
[[Category:Pyrophosphate esters]]
[[Category:Diterpenes]]
[[Category:Diterpenes]]


{{Biochem-stub}}

[[ja:ゲラニルゲラニルピロリン酸]]
[[fi:Geranyyligeranyylipyrofosfaatti]]

Latest revision as of 19:07, 9 July 2024

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
MeSH geranylgeranyl+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 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).
checkY verify (what is checkY☒N ?)

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).

[edit]

References

[edit]
  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.
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