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Isopentenyl pyrophosphate

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(Redirected fromIsopentenyl diphosphate)
Isopentenyl pyrophosphate
Skeletal formula of IPP
Skeletal formula of IPP
Ball-and-stick model of IPP
Ball-and-stick model of IPP
Names
IUPAC name
(Hydroxy-(3-methylbut-3-enoxy) phosphoryl)oxyphosphonic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSHisopentenyl+pyrophosphate
  • InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8) checkY[Pubchem]
    Key: NUHSROFQTUXZQQ-UHFFFAOYSA-N checkY[Pubchem]
  • CC(=C)CCOP(=O)(O)OP(=O)(O)O
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

Isopentenyl pyrophosphate (IPP,isopentenyl diphosphate, orIDP)[1] is an isoprenoid precursor. IPP is an intermediate in the classical,HMG-CoA reductase pathway (commonly called the mevalonate pathway) and in thenon-mevalonateMEP pathway of isoprenoid precursor biosynthesis. Isoprenoid precursors such as IPP, and its isomerDMAPP, are used by organisms in the biosynthesis ofterpenes andterpenoids.

Biosynthesis

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IPP is formed fromacetyl-CoA via the mevalonate pathway (the "upstream" part), and then isisomerized todimethylallyl pyrophosphate by the enzymeisopentenyl pyrophosphate isomerase.[2]

Mevalonate pathway
Simplified version of the steroid synthesis pathway with the intermediatesisopentenyl pyrophosphate (IPP),dimethylallyl pyrophosphate (DMAPP),geranyl pyrophosphate (GPP) andsqualene. Some intermediates are omitted. The color scheme does not correctly represent the origins of the isoprene units of GPP.

IPP can be synthesised via an alternative non-mevalonate pathway ofisoprenoid precursor biosynthesis, theMEP pathway, where it is formed from(E)-4-hydroxy-3-methyl-but-2-enyl pyrophosphate (HMB-PP) by the enzymeHMB-PP reductase (LytB, IspH). The MEP pathway is present in manybacteria,apicomplexanprotozoa such asmalaria parasites, and in theplastids of higherplants.[3]

See also

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References

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  1. ^Banerjee, A.; Sharkey, T. D. (9 July 2014)."Methylerythritol 4-phosphate (MEP) pathway metabolic regulation".Natural Product Reports.31 (8):1043–1055.doi:10.1039/C3NP70124G.PMID 24921065.
  2. ^Chang, Wei-chen; Song, Heng; Liu, Hung-wen; Liu, Pinghua (2013)."Current development in isoprenoid precursor biosynthesis and regulation".Current Opinion in Chemical Biology.17 (4):571–579.doi:10.1016/j.cbpa.2013.06.020.PMC 4068245.PMID 23891475.
  3. ^Wiemer, AJ; Hsiao, CH; Wiemer, DF (2010). "Isoprenoid metabolism as a therapeutic target in gram-negative pathogens".Current Topics in Medicinal Chemistry.10 (18):1858–71.doi:10.2174/156802610793176602.PMID 20615187.
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
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