ゲラニルゲラニル
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/02/13 01:17:57」(JST)
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Geranylgeranyl pyrophosphate
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Names |
IUPAC name
(2E,4E,6E)-3,5,7,11-Tetramethyldodeca-2,4,6,10-tetraene-1-pyrrophosphate
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Identifiers |
CAS Number
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6699-20-3 Y |
ChEBI |
CHEBI:48861 Y |
ChemSpider |
394418 Y |
IUPHAR/BPS
|
3052 |
Jmol interactive 3D |
Image |
MeSH |
geranylgeranyl+pyrophosphate |
PubChem |
447277 |
InChI
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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
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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
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SMILES
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O=P(O)(O)OP(=O)(O)OC/C=C(/CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C)C
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Properties |
Chemical formula
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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).
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Y verify (what is YN ?) |
Infobox references |
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Geranylgeranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of 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
- Geranylgeraniol
- Geranyl pyrophosphate
- Farnesyl pyrophosphate
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
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Mevalonate pathway |
to HMG-CoA |
- Acetyl-CoA
- Acetoacetyl-CoA
- HMG-CoA
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Ketone bodies |
- Acetone
- Acetoacetic acid
- β-Hydroxybutyric acid
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to DMAPP |
- Mevalonic acid
- Phosphomevalonic acid
- 5-Diphosphomevalonic acid
- Isopentenyl pyrophosphate
- Dimethylallyl pyrophosphate
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Geranyl- |
- Geranyl pyrophosphate
- Geranylgeranyl pyrophosphate
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Carotenoid |
- Prephytoene diphosphate
- Phytoene
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Non-mevalonate pathway |
- DOXP
- MEP
- CDP-ME
- CDP-MEP
- MEcPP
- HMB-PP
- IPP
- DMAPP
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To Cholesterol |
- Farnesyl pyrophosphate
- Squalene
- 2,3-Oxidosqualene
- Lanosterol
- Lanosterol
- Lathosterol
- 7-Dehydrocholesterol
- Cholesterol
- Lanosterol
- Zymosterol
- 7-Dehydrodesmosterol
- Desmosterol
- Cholesterol
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From Cholesterol
(to steroids) |
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
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Steroid hormones |
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Nonhuman |
Phytosterols |
- Stigmasterol
- Brassicasterol
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Ergosterols |
- Ergosterol
- Ergocalciferol
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UpToDate Contents
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English Journal
- Characterization and Functional Identification of a Gene Encoding Geranylgeranyl Diphosphate Synthase from Dunaliella bardawil.
- Liang MH1, Liang YJ2, Jin HH1, Jiang JG1.
- Journal of agricultural and food chemistry.J Agric Food Chem.2015 Sep 9;63(35):7805-12. doi: 10.1021/acs.jafc.5b02732. Epub 2015 Aug 25.
- Geranylgeranyl diphosphate synthase (GGPS) catalyzes the biosynthesis of geranylgeranyl diphosphate, a key precursor for carotenoid biosynthesis. In this study, a full-length cDNA encoding GGPS from Dunaliella bardawil (DbGGPS) was isolated by rapid amplification of cDNA ends (RACE) for the first ti
- PMID 26289929
- A phytoene desaturase homolog gene from the methanogenic archaeon Methanosarcina acetivorans is responsible for hydroxyarchaeol biosynthesis.
- Mori T1, Isobe K1, Ogawa T1, Yoshimura T1, Hemmi H2.
- Biochemical and biophysical research communications.Biochem Biophys Res Commun.2015 Sep 7. pii: S0006-291X(15)30518-0. doi: 10.1016/j.bbrc.2015.09.001. [Epub ahead of print]
- Hydroxyarchaeols are the typical core structures of archaeal membrane lipids uniquely produced by a limited number of methanogenic lineages, which are mainly classified in orders Methanosarcinales and Methanococcales. However, the biosynthetic machinery that is used for the biosynthesis of hydroxyar
- PMID 26361140
- Andrographis paniculata transcriptome provides molecular insights into tissue-specific accumulation of medicinal diterpenes.
- Garg A1, Agrawal L2, Misra RC3, Sharma S4, Ghosh S5.
- BMC genomics.BMC Genomics.2015 Sep 2;16:659. doi: 10.1186/s12864-015-1864-y.
- BACKGROUND: Kalmegh (Andrographis paniculata) has been widely exploited in traditional medicine for the treatment of infectious diseases and health disorders. Ent-labdane-related diterpene (ent-LRD) specialized (i.e., secondary) metabolites of kalmegh such as andrographolide, neoandrographolide and
- PMID 26328761
Japanese Journal
- 菌類およびコケ・シダ類における生理活性ジテルペノイドの生合成研究(学会賞,受賞業績)
- Crucial role of the Rap G protein signal in Notch activation and leukemogenicity of T-cell acute lymphoblastic leukemia.
- Biochemical and molecular characterization of orange- and tangerine-colored rice calli
Related Links
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Related Pictures
★リンクテーブル★
[★]
- 英
- geranylgeranyl
- 同
- geranylgeranyl基
[★]
ゲラニルゲラニルピロリン酸合成酵素、ゲラニルゲラニルピロリン酸シンターゼ
- 関
- geranylgeranyl-diphosphate geranylgeranyltransferase
[★]
ゲラニルゲラニル二リン酸ゲラニルゲラニルトランスフェラーゼ
- 関
- geranylgeranyl pyrophosphate synthase
[★]
タンパク質ゲラニルゲラニル化
- 関
- protein farnesylation、protein isoprenylation、protein prenylation
[★]
ゲラニルゲラニルトランスフェラーゼ、ゲラニルゲラニル転移酵素
[★]
- 関
- farnesylation、isoprenylation、prenylation