Dimethylallyl pyrophosphate: Difference between revisions
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new drawing (from german WP) showing unprotonated pyrophosphate |
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{{chembox |
{{chembox |
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| verifiedrevid = |
| verifiedrevid = 451182405 |
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| ImageFile = Dimethylallyl diphosphate.svg |
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| ImageSize = 200px |
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| ImageName = Skeletal formula |
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| ImageFile1 = Dimethylallyl-pyrophosphate-3D-balls.png |
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| ImageSize1 = 220px |
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| ImageName1 = Ball-and-stick model |
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| IUPACName = 3-Methyl-2-buten-1-yl trihydrogen diphosphate |
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| OtherNames = Dimethylallyl diphosphate; isoprenyl pyrophosphate; isoprenyl diphosphate |
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|Section1= |
|Section1={{Chembox Identifiers |
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| InChI =1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8) |
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| InChIKey = |
| InChIKey = CBIDRCWHNCKSTO-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| SMILES1 = O=P(OP(=O)(OC(C)(C)C=C)OC(C)(C)C=C)(OC(C)(C)C=C)OC(C)(C)C=C |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C20H36O7P2/c1-13-17(5,6)23-28(21,24-18(7,8)14-2)27-29(22,25-19(9,10)15-3)26-20(11,12)16-4/h13-16H,1-4H2,5-12H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = WTLAYXVNIWTZJI-UHFFFAOYSA-N |
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| CASNo=358-72-5 |
| CASNo=358-72-5 |
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| PubChem=647 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID= |
| ChemSpiderID=627 |
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| SMILES=CC(=CCOP(=O)(O)OP(=O)(O)O)C |
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| MeSHName=3,3-dimethylallyl+pyrophosphate |
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}} |
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|Section2= |
|Section2={{Chembox Properties |
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| C=5 | H=12 | O=7 | P=2 |
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| Formula=C<sub>5</sub>H<sub>12</sub>O<sub>7</sub>P<sub>2</sub> |
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| MolarMass=246.092 |
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|Section3= {{Chembox Hazards |
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'''Dimethylallyl pyrophosphate''' (or -diphosphate) (DMAPP) is an intermediate product of both [[mevalonic acid]] (MVA) pathway and DOXP/[[methylerythritol phosphate|MEP]] pathway. It is an isomer of [[isopentenyl pyrophosphate]] (IPP) and exists in virtually all life forms. The enzyme [[isopentenyl pyrophosphate isomerase]] catalyzes the isomerization of DMAPP from IPP. |
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'''Dimethylallyl pyrophosphate''' ('''DMAPP'''; or alternatively, '''dimethylallyl diphosphate''' ('''DMADP'''); also '''isoprenyl pyrophosphate''') is an isoprenoid precursor. It is a product of both the [[mevalonate pathway]] and the [[methylerythritol phosphate|MEP]] pathway of isoprenoid precursor biosynthesis. It is an isomer of [[isopentenyl pyrophosphate]] (IPP) and exists in virtually all life forms. The enzyme [[isopentenyl pyrophosphate isomerase]] catalyzes isomerization between DMAPP and IPP.<ref>{{cite journal|author1=Wang, W. |author2=Oldfield, E. |title=Bioorganometallic Chemistry with Ispg and Isph: Structure, Function, and Inhibition of the [Fe4s4] Proteins Involved in Isoprenoid Biosynthesis|journal=Angew. Chem. Int. Ed.|year=2014|volume=53|issue=17|pages=4294–4310|doi=10.1002/anie.201306712|pmc=3997630|pmid=24481599}}</ref> |
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Precursor of DMAPP in the MVA pathway is mevalonic acid, and [[2-C-methyl-D-erythritol-e-P]] in the [[MEP/DOXP pathway]]. |
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In the mevalonate pathway DMAPP is synthesised from [[mevalonic acid]]. In contrast, DMAPP is synthesised from [[(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate|HMBPP]] in the [[Non-mevalonate pathway|MEP pathway]]. |
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At present, it is believed that there is crossover between the two pathways in organisms |
At present, it is believed that there is crossover between the two pathways in organisms |
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that use both pathways to create [[terpene]]s and [[terpenoid]]s, such as in plants, and that DMAPP is the crossover product. |
that use both pathways to create [[terpene]]s and [[terpenoid]]s, such as in plants, and that DMAPP is the crossover product. |
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[[ |
[[File:Mevalonate pathway.svg|350px|thumb|center|Mevalonate pathway]] |
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[[ |
[[File:Sterol synthesis.svg|thumb|center|350px|Simplified version of the steroid synthesis pathway with the intermediates isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), [[geranyl pyrophosphate]] (GPP) and squalene shown. Some intermediates are omitted.]] |
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==References== |
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<references /> |
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==External links== |
==External links== |
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{{Cholesterol metabolism intermediates}} |
{{Cholesterol metabolism intermediates}} |
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{{Terpenoids}} |
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[[Category: |
[[Category:Pyrophosphate esters]] |
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[[Category:Hemiterpenes]] |
[[Category:Hemiterpenes]] |
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{{biochem-stub}} |
{{biochem-stub}} |
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[[de:Dimethylallylpyrophosphat]] |
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[[ja:ジメチルアリル二リン酸]] |
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[[pt:Difosfato de dimetilalilo]] |
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[[sr:Dimetilalil pirofosfat]] |
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[[fi:Dimetyyliallyylipyrofosfaatti]] |
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[[id:Dimetilalil Pirofosfat]] |
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