Dimethylallyl pyrophosphate

Dimethylallyl pyrophosphate

Names
IUPAC name (hydroxy-(3-methylbut-2-enoxy) phosphoryl) oxyphosphonic acid
Other names Dimethylallyl diphosphate; isoprenyl pyrophosphate; isoprenyl diphosphate
Identifiers
CAS Registry Number	358-72-5 Y
ChemSpider	19951350 Y
InChI InChI=1S/C20H36O7P2/c1-13-17(5,6)23-28(21,24-18(7,8)14-2)27-29(22,25-19(9,10)15-3)26-20(11,12)16-4/h13-16H,1-4H2,5-12H3 Y Key: WTLAYXVNIWTZJI-UHFFFAOYSA-N Y InChI=1/C20H36O7P2/c1-13-17(5,6)23-28(21,24-18(7,8)14-2)27-29(22,25-19(9,10)15-3)26-20(11,12)16-4/h13-16H,1-4H2,5-12H3 Key: WTLAYXVNIWTZJI-UHFFFAOYAD
Jmol-3D images	Image Image
MeSH	3,3-dimethylallyl+pyrophosphate
PubChem	647
SMILES CC(=CCOP(=O)(O)OP(=O)(O)O)C O=P(OP(=O)(OC(C)(C)C=C)OC(C)(C)C=C)(OC(C)(C)C=C)OC(C)(C)C=C
Properties
Chemical formula	C5H12O7P2
Molar mass	246.092
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Dimethylallyl pyrophosphate (or incorrectly, -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.

Mevalonate pathway

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