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Geranylgeranyl pyrophosphate

Geranylgeranyl pyrophosphate is an intermediate in the biosynthesis of diterpenes and diterpenoids.[1] It is also the precursor to carotenoids, gibberellins, tocopherols, and chlorophylls.

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
  • 6699-20-3 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:48861 Y
ChemSpider
  • 394418 Y
  • 3052
MeSH geranylgeranyl+pyrophosphate
  • 447277
UNII
  • N21T0D88LX Y
  • 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
  • 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).
Y verify (what is YN ?)

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

  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.{{cite journal}}: CS1 maint: uses authors parameter (link)
  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.

geranylgeranyl, pyrophosphate, intermediate, biosynthesis, diterpenes, diterpenoids, also, precursor, carotenoids, gibberellins, tocopherols, chlorophylls, namespreferred, iupac, name, tetramethylhexadeca, tetraen, trihydrogen, diphosphateother, names, geranyl. Geranylgeranyl pyrophosphate is an intermediate in the biosynthesis of diterpenes and diterpenoids 1 It is also the precursor to carotenoids gibberellins tocopherols and chlorophylls Geranylgeranyl pyrophosphate NamesPreferred IUPAC name 2E 6E 10E 3 7 11 15 Tetramethylhexadeca 2 6 10 14 tetraen 1 yl trihydrogen diphosphateOther names geranylgeranyl diphosphatetrans geranylgeranyl diphosphateIdentifiersCAS Number 6699 20 3 Y3D model JSmol Interactive imageChEBI CHEBI 48861 YChemSpider 394418 YIUPHAR BPS 3052MeSH geranylgeranyl pyrophosphatePubChem CID 447277UNII N21T0D88LX YInChI 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 YKey OINNEUNVOZHBOX QIRCYJPOSA N YInChI 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 QIRCYJPOBRSMILES O P O O OP O O OC C C CC C C C CC C C C CC C C C C CPropertiesChemical formula C 20H 36O 7P 2Molar mass 450 449 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references 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 EditFarnesyl pyrophosphate Geranylgeraniol Geranyl pyrophosphateReferences 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 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint uses authors parameter link 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 This biochemistry article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Geranylgeranyl pyrophosphate amp oldid 1137685117, wikipedia, wiki, book, books, library,

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