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 (Jmol)
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, -diphosphate (DMADP); also isoprenyl pyrophosphate) is an intermediate product of both mevalonic acid (MVA) pathway and DOXP/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.[1]

Precursor of DMAPP in the MVA pathway is mevalonic acid, and HMBPP in the MEP/DOXP 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.

References[edit]

  1. ^ Wang, W.; Oldfield, E. (2014). "Bioorganometallic Chemistry with Ispg and Isph: Structure, Function, and Inhibition of the [Fe4s4] Proteins Involved in Isoprenoid Biosynthesis". Angew. Chem., Int. Ed. 53: 4294–4310. doi:10.1002/anie.201306712. 

External links[edit]