Isopentenyl pyrophosphate

Isopentenyl pyrophosphate

Names
IUPAC name (hydroxy-(3-methylbut-3-enoxy) phosphoryl)oxyphosphonic acid
Identifiers
CAS Number	358-71-4
3D model (Jmol)	Interactive image
ChEBI	CHEBI:128769
ChemSpider	13115335
MeSH	isopentenyl+pyrophosphate
PubChem	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	C5H12O7P2
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

Isopentenyl pyrophosphate (IPP, isopentenyl diphosphate, or IDP)^[1] is an intermediate in the classical, HMG-CoA reductase pathway (commonly called the mevalonate pathway), and is used by organisms in the biosynthesis of terpenes and terpenoids. 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 synthesized via the alternative, non-mevalonate pathway of isoprenoid biosynthesis instead, 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 non-mevalonate pathway is utilized by many bacteria, apicomplexan protozoa such as malaria parasites, and the plastids of higher plants.^[3]

See also

• Dimethylallyltranstransferase

References

1. http://pubs.rsc.org/en/Content/ArticleLanding/2014/NP/C3NP70124G#!divAbstract
2. Chang, Wei-chen; Song, Heng; Liu, Hung-wen; Liu, Pinghua "Current development in isoprenoid precursor biosynthesis and regulation" Current Opinion in Chemical Biology, 2013 volume 17, pp. 571-579. doi:10.1016/j.cbpa.2013.06.020
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. PMID 20615187.