Isopentenyl pyrophosphate

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
MeSH isopentenyl+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 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).
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Isopentenyl pyrophosphate (IPP, isopentenyl diphosphate, or IDP)[1] is an isoprenoid precursor. IPP is an intermediate in the classical, HMG-CoA reductase pathway (commonly called the mevalonate pathway) and in the non-mevalonate MEP pathway of isoprenoid precursor biosynthesis. Isoprenoid precursors such as IPP, and its isomer DMAPP, are used by organisms in the biosynthesis of terpenes and terpenoids.

Biosynthesis

IPP is formed from acetyl-CoA via the mevalonate pathway (the "upstream" part), and then is isomerized to dimethylallyl pyrophosphate by the enzyme isopentenyl pyrophosphate isomerase.[2]

Mevalonate pathway
Simplified version of the steroid synthesis pathway with the intermediates isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), geranyl pyrophosphate (GPP) and squalene. 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 of isoprenoid precursor biosynthesis, the MEP pathway, where it is formed from (E)-4-hydroxy-3-methyl-but-2-enyl pyrophosphate (HMB-PP) by the enzyme HMB-PP reductase (LytB, IspH). The MEP pathway is present in many bacteria, apicomplexan protozoa such as malaria parasites, and in the plastids of higher plants.[3]

See also

References

  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.