Isopentenyl pyrophosphate

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Isopentenyl pyrophosphate
Skeletal formula of IPP
Ball-and-stick model of IPP
IUPAC name
(hydroxy-(3-methylbut-3-enoxy) phosphoryl)oxyphosphonic acid
358-71-4 YesY
ChEBI CHEBI:128769 YesY
ChemSpider 13115335 YesY
Jmol interactive 3D Image
MeSH isopentenyl+pyrophosphate
PubChem 15983957
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]

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[edit]


  1. ^!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.