Dimethylallyl pyrophosphate

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Dimethylallyl pyrophosphate
Skeletal formula
Ball-and-stick model
IUPAC name
(hydroxy-(3-methylbut-2-enoxy) phosphoryl) oxyphosphonic acid
Other names
Dimethylallyl diphosphate; isoprenyl pyrophosphate; isoprenyl diphosphate
358-72-5 YesY
ChemSpider 19951350 YesY
Jmol-3D images Image
MeSH 3,3-dimethylallyl+pyrophosphate
PubChem 647
Molar mass 246.092
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 YesY verify (what isYesY/N?)
Infobox references

Dimethylallyl pyrophosphate (or alternatively, -diphosphate) (DMAPP) 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.

Precursor of DMAPP in the MVA pathway is mevalonic acid, and 2-C-methyl-D-erythritol-e-P 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.

External links[edit]