Dimethylallyl pyrophosphate

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Dimethylallyl pyrophosphate
Skeletal formula
Ball-and-stick model
Names
IUPAC name
(hydroxy-(3-methylbut-2-enoxy) phosphoryl) oxyphosphonic acid
Other names
Dimethylallyl diphosphate; isoprenyl pyrophosphate; isoprenyl diphosphate
Identifiers
3D model (JSmol)
ChemSpider
MeSH 3,3-dimethylallyl+pyrophosphate
Properties
C5H12O7P2
Molar mass 246.092
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

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.[1]

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.

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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