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Dimethylallyl pyrophosphate

In this article, we will explore the fascinating world of Dimethylallyl pyrophosphate and how it has impacted our lives in unimaginable ways. Dimethylallyl pyrophosphate has been the object of study, controversy and admiration throughout history, and its influence extends to practically all aspects of our society. From its origins to its modern evolution, Dimethylallyl pyrophosphate has left an indelible mark on humanity, challenging our perceptions and provoking deep reflections on who we are and where we are headed. Join us on this journey to discover the importance of Dimethylallyl pyrophosphate in our lives and in the world around us.

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Dimethylallyl pyrophosphate
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
IUPAC name
3-Methyl-2-buten-1-yl trihydrogen diphosphate
Other names
Dimethylallyl diphosphate; isoprenyl pyrophosphate; isoprenyl diphosphate
Identifiers
3D model (JSmol)
ChemSpider
MeSH 3,3-dimethylallyl+pyrophosphate
  • 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
C5H12O7P2
Molar mass 246.092 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
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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 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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