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Geranyl pyrophosphate information


Geranyl pyrophosphate
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
(2E)-3,7-Dimethylocta-2,6-dien-1-yl trihydrogen diphosphate
Identifiers
CAS Number
  • 763-10-0 ☒N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17211 checkY
ChEMBL
  • ChEMBL41342 checkY
ChemSpider
  • 393471 checkY
DrugBank
  • DB02552 checkY
IUPHAR/BPS
  • 3051
MeSH Geranyl+pyrophosphate
PubChem CID
  • 445995
CompTox Dashboard (EPA)
  • DTXSID801315430 Edit this at Wikidata
InChI
  • 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+ checkY
    Key: GVVPGTZRZFNKDS-JXMROGBWSA-N checkY
  • 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
SMILES
  • O=P(O)(O)OP(=O)(OC/C=C(/CC\C=C(/C)C)C)O
Properties
Chemical formula
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).
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Infobox references

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.

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Geranyl pyrophosphate

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

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Pyrophosphate

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inorganic pyrophosphate has a reference range of 0.58–3.78 μM (95% prediction interval). Isopentenyl pyrophosphate converts to geranyl pyrophosphate, the precursor...

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Terpene

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isopentenyl pyrophosphate isomerase. IPP and DMAPP condense to give geranyl pyrophosphate, the precursor to monoterpenes and monoterpenoids. Geranyl pyrophosphate...

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Farnesyl pyrophosphate

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3-isopentenyl pyrophosphate to form geranyl pyrophosphate: Geranyl pyrophosphate then reacts with another molecule of 3-isopentenyl pyrophosphate to form farnesyl...

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Limonene

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the ketone-containing carvone. In nature, limonene is formed from geranyl pyrophosphate, via cyclization of a neryl carbocation or its equivalent as shown...

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Dimethylallyl pyrophosphate

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Dimethylallyl pyrophosphate (DMAPP; or alternatively, dimethylallyl diphosphate (DMADP); also isoprenyl pyrophosphate) is an isoprenoid precursor. It...

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Geraniol

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resulting from fermentation of sorbic acid by lactic acid bacteria. Geranyl pyrophosphate is important in biosynthesis of other terpenes such as myrcene and...

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Linalool

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linalool are referred to as linalyl, e.g. linalyl pyrophosphate, an isomer of geranyl pyrophosphate. The word linalool is based on linaloe (a type of...

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Geranylgeranyl pyrophosphate

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differentiate into eggs and spermatozoa (sperm). Farnesyl pyrophosphate Geranylgeraniol Geranyl pyrophosphate Davis, Edward M.; Croteau, Rodney (2000). "Cyclization...

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Isopentenyl pyrophosphate

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Isopentenyl pyrophosphate (IPP, isopentenyl diphosphate, or IDP) is an isoprenoid precursor. IPP is an intermediate in the classical, HMG-CoA reductase...

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Terpenoid

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carbocationic intermediates produced from geranyl pyrophosphate. Analogously hydrolysis of intermediates from farnesyl pyrophosphate gives sesquiterpenoids, and hydrolysis...

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Monoterpene

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isopentenyl pyrophosphate isomerase. Geranyl pyrophosphate is the precursor to monoterpenes (and hence monoterpenoids). Elimination of the pyrophosphate group...

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Isoprene

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of plants. One of the two end-products of MEP pathway, dimethylallyl pyrophosphate (DMAPP), is cleaved by the enzyme isoprene synthase to form isoprene...

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Camphor

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biosynthesis, camphor is produced from geranyl pyrophosphate, via cyclisation of linaloyl pyrophosphate to bornyl pyrophosphate, followed by hydrolysis to borneol...

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Pinene

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α-Pinene and β-pinene are both produced from geranyl pyrophosphate, via cyclisation of linaloyl pyrophosphate followed by loss of a proton from the carbocation...

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Triterpene

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biosynthesized through the head-to-head condensation of two farnesyl pyrophosphate units. This coupling converts a pair of C15 components into a C30 product...

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Fenchol

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species of Aster. It is biosynthesized from geranyl pyrophosphate via isomerization to linalyl pyrophosphate. Oxidation of fenchol gives fenchone. Datasheet...

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Geranyl diphosphate diphosphatase

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Geranyl diphosphate diphosphatase (EC 3.1.7.11, geraniol synthase', geranyl pyrophosphate pyrophosphatase) is an enzyme with systematic name geranyl-diphosphate...

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Sesquiterpene

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atmosphere. The reaction of geranyl pyrophosphate with isopentenyl pyrophosphate results in the 15-carbon farnesyl pyrophosphate (FPP), which is an intermediate...

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Squalene

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Archaea. Squalene is biosynthesised by coupling two molecules of farnesyl pyrophosphate. The condensation requires NADPH and the enzyme squalene synthase. Click...

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Cholecalciferol

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Acyclic Citronellal Citral Citronellol Geraniol Geranyl pyrophosphate Halomon Linalool Monocyclic Grapefruit mercaptan Menthol p-Cymene Thujaplicins (Hinokitiol)...

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Terpineol

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4-terpineol. The biosynthesis of α-terpineol proceeds from geranyl pyrophosphate, which releases pyrophosphate to give the terpinyl cation. This carbocation is...

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Secologanin

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Secologanin is a secoiridoid monoterpene synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceeds with dopamine or...

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Myrcene

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biosynthesize myrcene via geranyl pyrophosphate (GPP), which isomerizes into linalyl pyrophosphate. The release of the pyrophosphate (OPP) and a proton completes...

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Lycopene

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dimethylallyl pyrophosphate. This is then condensed with three molecules of isopentenyl pyrophosphate (an isomer of dimethylallyl pyrophosphate), to give...

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Terpinene

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isomerization of geranyl pyrophosphate to linalyl pyrophosphate (LPP). LPP then forms a resonance-stabilized cation by loss of the pyrophosphate group. Cyclization...

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Phytochemical

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Acyclic Citronellal Citral Citronellol Geraniol Geranyl pyrophosphate Halomon Linalool Monocyclic Grapefruit mercaptan Menthol p-Cymene Thujaplicins (Hinokitiol)...

Word Count : 2226

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