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 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.{{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}}

In the mevalonate pathway, DMAPP is synthesised from mevalonic acid. In contrast, DMAPP is synthesised from HMBPP in the MEP pathway.

At present, it is believed that there is crossover between the two pathways in organisms

that use both pathways to create terpenes and terpenoids, such as in plants, and that DMAPP is the crossover product.

File:Mevalonate pathway.svg

File:Sterol synthesis.svg (GPP) and squalene shown. Some intermediates are omitted.]]