View source for Dimethylallyl pyrophosphate

{{chembox
| verifiedrevid = 451182405
| ImageFile = Dimethylallyl diphosphate.svg
| ImageSize = 200px
| ImageName = Skeletal formula
| ImageFile1 = Dimethylallyl-pyrophosphate-3D-balls.png
| ImageSize1 = 220px
| ImageName1 = Ball-and-stick model
| IUPACName = 3-Methyl-2-buten-1-yl trihydrogen diphosphate
| OtherNames = Dimethylallyl diphosphate; isoprenyl pyrophosphate; isoprenyl diphosphate
|Section1={{Chembox Identifiers
| 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)
| InChIKey = CBIDRCWHNCKSTO-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=358-72-5
| PubChem=647
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=627 
| SMILES=CC(=CCOP(=O)(O)OP(=O)(O)O)C
| MeSHName=3,3-dimethylallyl+pyrophosphate
 }}
|Section2={{Chembox Properties
| C=5 | H=12 | O=7 | P=2
 }}
}}

'''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>

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]].

At present, it is believed that there is crossover between the two pathways in organisms
that use both pathways to create [[terpene]]s and [[terpenoid]]s, such as in plants, and that DMAPP is the crossover product.

[[File:Mevalonate pathway.svg|350px|thumb|center|Mevalonate pathway]]

[[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.]]

==References==
<references />

==External links==

{{Cholesterol metabolism intermediates}}
{{Terpenoids}}

[[Category:Pyrophosphate esters]]
[[Category:Hemiterpenes]]

{{biochem-stub}}