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Dimethylallyl pyrophosphate

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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
  • 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

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.

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.

External links

Cholesterol and steroid metabolic intermediates
Mevalonate pathway
to HMG-CoA
Ketone bodies
to DMAPP
Geranyl-
Carotenoid
Non-mevalonate pathway
To Cholesterol
From Cholesterol
to Steroid hormones
Nonhuman
To Sitosterol
To Ergocalciferol
Types of terpenes and terpenoids (# of isoprene units)
Basic forms:
  • Acyclic (linear, cis and trans forms)
  • Monocyclic (single ring)
  • Bicyclic (2 rings)
  • Iridoids (cyclopentane ring)
  • Iridoid glycosides (iridoids bound to a sugar)
  • Steroids (4 rings)
Hemiterpenoids (1)
Monoterpenes
(C10H16)(2)
Acyclic
Monocyclic
Bicyclic
Monoterpenoids
(2,modified)
Acyclic
Monocyclic
Bicyclic
Sesquiterpenoids (3)
Diterpenoids (4)
Acyclic
Monocyclic
Bicyclic
Tricyclic
Tetracyclic
Resin acids
Sesterterpenoids (5)
  • Geranylfarnesol
Triterpenoids (6)
Steroids
Other
Sesquarterpenes/oids (7)
  • Ferrugicadiol
  • Tetraprenylcurcumene
Tetraterpenoids
(Carotenoids) (8)
Carotenes
Xanthophylls:
Polyterpenoids (many)
Norisoprenoids (modified)
  • 3-oxo-α-ionol
  • 7,8-dihydroionone
Synthesis
Activated isoprene forms
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