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Geranyl pyrophosphate

Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), is the pyrophosphate ester of the terpenoid geraniol. Its salts are colorless. It is a precursor to many natural products.

Geranyl pyrophosphate
Names
Preferred IUPAC name
(2E)-3,7-Dimethylocta-2,6-dien-1-yl trihydrogen diphosphate
Identifiers
  • 763-10-0 N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17211 Y
ChEMBL
  • ChEMBL41342 Y
ChemSpider
  • 393471 Y
DrugBank
  • DB02552 Y
  • 3051
MeSH Geranyl+pyrophosphate
  • 445995
  • InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+ Y
    Key: GVVPGTZRZFNKDS-JXMROGBWSA-N Y
  • InChI=1/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+
    Key: GVVPGTZRZFNKDS-JXMROGBWBE
  • O=P(O)(O)OP(=O)(OC/C=C(/CC\C=C(/C)C)C)O
Properties
C10H17O7P2
Molar mass 311,19
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Occurrence

GPP is an intermediate in the isoprenoid biosynthesis pathway that produces longer prenyl chains such as farnesyl pyrophosphate and geranylgeranyl pyrophosphate as well as many terpenes.[1] It can be prepared in the laboratory from geraniol.[2]

 
Isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) are condensed by geranyl pyrophosphate synthase (dimethylallyltranstransferase) to produce geranyl pyrophosphate (GPP) and pyrophosphate. The carbon skeletons of DMAPP and IPP have been colored to indicate their location in GPP.

Related compounds

See also

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. ^ Andrew B. Woodside, Zheng Huang, C. Dale Poulter (1988). "Trisammonium Geranyl Diphosphate". Organic Syntheses. 66: 211. doi:10.15227/orgsyn.066.0211.{{cite journal}}: CS1 maint: multiple names: authors list (link)

Further reading

  • Kulkarni RS, Pandit SS, Chidley HG, Nagel R, Schmidt A, Gershenzon J, Pujari KH, Giri AP and Gupta VS, 2013, Characterization of three novel isoprenyl diphosphate synthases from the terpenoid rich mango fruit. Plant Physiology and Biochemistry, 71, 121–131.

geranyl, pyrophosphate, also, known, geranyl, diphosphate, pyrophosphate, ester, terpenoid, geraniol, salts, colorless, precursor, many, natural, products, namespreferred, iupac, name, dimethylocta, dien, trihydrogen, diphosphateidentifierscas, number, model, . Geranyl pyrophosphate GPP also known as geranyl diphosphate GDP is the pyrophosphate ester of the terpenoid geraniol Its salts are colorless It is a precursor to many natural products Geranyl pyrophosphate NamesPreferred IUPAC name 2E 3 7 Dimethylocta 2 6 dien 1 yl trihydrogen diphosphateIdentifiersCAS Number 763 10 0 N3D model JSmol Interactive imageChEBI CHEBI 17211 YChEMBL ChEMBL41342 YChemSpider 393471 YDrugBank DB02552 YIUPHAR BPS 3051MeSH Geranyl pyrophosphatePubChem CID 445995InChI InChI 1S C10H20O7P2 c1 9 2 5 4 6 10 3 7 8 16 19 14 15 17 18 11 12 13 h5 7H 4 6 8H2 1 3H3 H 14 15 H2 11 12 13 b10 7 YKey GVVPGTZRZFNKDS JXMROGBWSA N YInChI 1 C10H20O7P2 c1 9 2 5 4 6 10 3 7 8 16 19 14 15 17 18 11 12 13 h5 7H 4 6 8H2 1 3H3 H 14 15 H2 11 12 13 b10 7 Key GVVPGTZRZFNKDS JXMROGBWBESMILES O P O O OP O OC C C CC C C C C C OPropertiesChemical formula C10H17O7P2Molar mass 311 19Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Occurrence 2 Related compounds 3 See also 4 References 5 Further readingOccurrence EditGPP is an intermediate in the isoprenoid biosynthesis pathway that produces longer prenyl chains such as farnesyl pyrophosphate and geranylgeranyl pyrophosphate as well as many terpenes 1 It can be prepared in the laboratory from geraniol 2 Isopentenyl pyrophosphate IPP and dimethylallyl pyrophosphate DMAPP are condensed by geranyl pyrophosphate synthase dimethylallyltranstransferase to produce geranyl pyrophosphate GPP and pyrophosphate The carbon skeletons of DMAPP and IPP have been colored to indicate their location in GPP Related compounds EditGeraniol Farnesyl pyrophosphate Geranylgeranyl pyrophosphateSee also EditDimethylallyltranstransferaseReferences 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 Andrew B Woodside Zheng Huang C Dale Poulter 1988 Trisammonium Geranyl Diphosphate Organic Syntheses 66 211 doi 10 15227 orgsyn 066 0211 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Further reading EditKulkarni RS Pandit SS Chidley HG Nagel R Schmidt A Gershenzon J Pujari KH Giri AP and Gupta VS 2013 Characterization of three novel isoprenyl diphosphate synthases from the terpenoid rich mango fruit Plant Physiology and Biochemistry 71 121 131 This biochemistry article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Geranyl pyrophosphate amp oldid 1121699282, wikipedia, wiki, book, books, library,

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