Isopentenyl pyrophosphate

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.

Isopentenyl pyrophosphate

Names
IUPAC name (hydroxy-(3-methylbut-3-enoxy) phosphoryl)oxyphosphonic acid
Identifiers
CAS Number	358-71-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:128769
ChemSpider	13115335
MeSH	isopentenyl+pyrophosphate
PubChem CID	15983957
InChI 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)/p-3 Key: NUHSROFQTUXZQQ-UHFFFAOYSA-K InChI=1/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)/p-3 Key: NUHSROFQTUXZQQ-DFZHHIFOAI
SMILES CC(=C)CCOP(=O)([O-])OP(=O)([O-])[O-]
Properties
Chemical formula	C5H9O7P2
Molar mass	246.092
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 shown. Some intermediates are omitted. Please note the color scheme is for illustration only and 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

• Dimethylallyltranstransferase

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.