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.
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| Names | |
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| IUPAC name
(Hydroxy-(3-methylbut-3-enoxy) phosphoryl)oxyphosphonic acid
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| Identifiers | |
3D model (JSmol)
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| MeSH | isopentenyl pyrophosphate |
PubChem CID
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CompTox Dashboard (EPA)
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| 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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Biosynthesis
editIPP 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]
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
editReferences
edit- ^ 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.
- ^ 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.
- ^ 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.