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Isopentenyl pyrophosphate information


Isopentenyl pyrophosphate
Skeletal formula of IPP
Ball-and-stick model of IPP
Names
IUPAC name
(Hydroxy-(3-methylbut-3-enoxy) phosphoryl)oxyphosphonic acid
Identifiers
CAS Number
  • 358-71-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:128769 checkY
ChemSpider
  • 1158 checkY
MeSH isopentenyl+pyrophosphate
PubChem CID
  • 1195
InChI
  • InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8) checkY[Pubchem]
    Key: NUHSROFQTUXZQQ-UHFFFAOYSA-N checkY[Pubchem]
SMILES
  • CC(=C)CCOP(=O)(O)OP(=O)(O)O
Properties
Chemical formula
C5H12O7P2
Molar mass 246.092 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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Infobox references

Isopentenyl pyrophosphate (IPP, isopentenyl diphosphate, or IDP)[1] is an isoprenoid precursor. IPP is an intermediate in the classical, HMG-CoA reductase pathway (commonly called the mevalonate pathway) and in the non-mevalonate MEP pathway of isoprenoid precursor biosynthesis. Isoprenoid precursors such as IPP, and its isomer DMAPP, are used by organisms in the biosynthesis of terpenes and terpenoids.

  1. ^ Banerjee, A.; Sharkey, T. D. (9 July 2014). "Methylerythritol 4-phosphate (MEP) pathway metabolic regulation". Natural Product Reports. 31 (8): 1043–1055. doi:10.1039/C3NP70124G. PMID 24921065.

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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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Dimethylallyl pyrophosphate

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It is an isomer of isopentenyl pyrophosphate (IPP) and exists in virtually all life forms. The enzyme isopentenyl pyrophosphate isomerase catalyzes isomerization...

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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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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...

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Terpene

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units are provided in the form of dimethylallyl pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP). DMAPP and IPP are structural isomers to each...

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Natural rubber

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which converts three monomers of isopentenyl pyrophosphate into farnesyl pyrophosphate. The farnesyl pyrophosphate can bind to rubber transferase to...

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Mevalonate pathway

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produces two five-carbon building blocks called isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP), which are used to make isoprenoids...

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Dimethylallyltranstransferase

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dimethylallylpyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP) into farnesylpyrophosphate (FPP). Pyrophosphate is also involved, as both a reactant...

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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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Terpenoid

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

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Limonene

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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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Isoprene

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units in biological systems is dimethylallyl pyrophosphate (DMAPP) and its isomer isopentenyl pyrophosphate (IPP). The plural 'isoprenes' is sometimes used...

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Astaxanthin

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biosynthesis starts with three molecules of isopentenyl pyrophosphate (IPP) and one molecule of dimethylallyl pyrophosphate (DMAPP) that are combined by IPP isomerase...

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Geranylgeranyl pyrophosphate

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from farnesyl pyrophosphate by the addition of an isoprene unit from isopentenyl pyrophosphate. In Drosophila, geranylgeranyl pyrophosphate is synthesised...

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Monoterpene

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pathways, IPP is isomerized to DMAPP by the enzyme isopentenyl pyrophosphate isomerase. Geranyl pyrophosphate is the precursor to monoterpenes (and hence monoterpenoids)...

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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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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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Diphosphomevalonate decarboxylase

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(adding ATP isopentenyl-diphosphate-forming). Other names in common use include pyrophosphomevalonate decarboxylase, mevalonate-5-pyrophosphate decarboxylase...

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TRNA dimethylallyltransferase

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isopentenyltransferase, Delta2-isopentenyl pyrophosphate:tRNA-Delta2-isopentenyl transferase, Delta2-isopentenyl pyrophosphate:transfer ribonucleic acid...

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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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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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Secondary metabolite

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Structural formula for isopentenyl pyrophosphate (IPP), the carbon atoms of which constitute building blocks in terpenes. Because of the presence of five...

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Metabolism

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isoprene units donated from the reactive precursors isopentenyl pyrophosphate and dimethylallyl pyrophosphate. These precursors can be made in different ways...

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Saponin

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common a terpene synthase N terminal domain (protein domain) Activated isoprene forms Isopentenyl pyrophosphate (IPP) Dimethylallyl pyrophosphate (DMAPP)...

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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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common a terpene synthase N terminal domain (protein domain) Activated isoprene forms Isopentenyl pyrophosphate (IPP) Dimethylallyl pyrophosphate (DMAPP)...

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