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Dimethylallyl pyrophosphate

From Wikipedia, the free encyclopedia
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
MeSH3,3-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 mass246.092 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Dimethylallyl pyrophosphate (DMAPP; or alternatively,dimethylallyl diphosphate (DMADP); alsoisoprenyl pyrophosphate) is an isoprenoid precursor. It is a product of both themevalonate pathway and theMEP pathway of isoprenoid precursor biosynthesis. It is an isomer ofisopentenyl pyrophosphate (IPP) and exists in virtually all life forms. The enzymeisopentenyl pyrophosphate isomerase catalyzes isomerization between DMAPP and IPP.[1]

In the mevalonate pathway, DMAPP is synthesised frommevalonic acid. In contrast, DMAPP is synthesised fromHMBPP in theMEP pathway.

At present, it is believed that there is crossover between the two pathways in organismsthat use both pathways to createterpenes andterpenoids, 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.

External links

[edit]
Mevalonate pathway
toHMG-CoA
Ketone bodies
toDMAPP
Geranyl-
Carotenoid
Non-mevalonate pathway
ToCholesterol
FromCholesterol
toSteroid hormones
Nonhuman
ToSitosterol
ToErgocalciferol
Types ofterpenes andterpenoids (# ofisoprene units)
Basic forms:
  • Acyclic (linear,cis andtrans 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
Stub icon

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