Dimethylallyl pyrophosphate

Dimethylallyl pyrophosphate

Skeletal formula
Ball-and-stick model
Names
IUPAC name 3-Methyl-2-buten-1-yl trihydrogen diphosphate
Other names Dimethylallyl diphosphate; isoprenyl pyrophosphate; isoprenyl diphosphate
Identifiers
CAS Number	358-72-5  Y
3D model (JSmol)	Interactive image
ChemSpider	627  Y
MeSH	3,3-dimethylallyl+pyrophosphate
PubChem CID	647
CompTox Dashboard (EPA)	DTXSID70189331
InChI 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) Key: CBIDRCWHNCKSTO-UHFFFAOYSA-N
SMILES CC(=CCOP(=O)(O)OP(=O)(O)O)C
Properties
Chemical formula	C5H12O7P2
Molar mass	246.092 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y  verify  (what is  YN ?) 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.

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.

References

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 (17): 4294–4310. doi:10.1002/anie.201306712. PMC   3997630 . PMID   24481599.