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Dimethylallyl pyrophosphate





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(Redirected from Dimethylallyl diphosphate)
 


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]

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

3D model (JSmol)

ChemSpider
MeSH 3,3-dimethylallyl+pyrophosphate

PubChem CID

CompTox Dashboard (EPA)

  • 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

  • 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).

checkY verify (what is checkY☒N ?)

Infobox references

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

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 (17): 4294–4310. doi:10.1002/anie.201306712. PMC 3997630. PMID 24481599.
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    Last edited on 29 June 2024, at 19:52  





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    This page was last edited on 29 June 2024, at 19:52 (UTC).

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