Isopentenyl pyrophosphate: Difference between revisions

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| ImageName = Skeletal formula of IPP

| ImageFile1 = Isopentenyl-pyrophosphate-3D-balls.png

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| ImageName1 = Ball-and-stick model of IPP

| IUPACName = (-(3-methylbut-3-enoxy) phosphoryl)oxyphosphonic acid

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| = /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)

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| SMILES = CC(=C)CCOP(=O)(O)OP(=O)(O)O

| MeSHName=isopentenyl+pyrophosphate

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| C=5|H=12|O=7|P=2

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'''Isopentenyl pyrophosphate''' ('''IPP''', '''isopentenyl diphosphate''', or '''IDP''')<ref>{{cite journal|url=http://pubs.rsc.org/en/Content/ArticleLanding/2014/NP/C3NP70124G|title=Methylerythritol 4-phosphate (MEP) pathway metabolic regulation|first1=A.|last1=Banerjee|first2=T. D.|last2=Sharkey|date=9 July 2014|journal=Natural Product Reports|volume=31|issue=8|doi=10.1039/C3NP70124G|pages=1043–1055|pmid=24921065}}</ref> 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 [[Dimethylallyl pyrophosphate|DMAPP]], are used by organisms in the biosynthesis of [[terpene]]s and [[terpenoid]]s.

== 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]].<ref>{{cite journal|author1=Chang, Wei-chen|author2=Song, Heng|author3=Liu, Hung-wen|author4=Liu, Pinghua|title=Current development in isoprenoid precursor biosynthesis and regulation|journal=Current Opinion in Chemical Biology|year=2013|volume=17|issue=4|pages=571–579|doi=10.1016/j.cbpa.2013.06.020|pmc=4068245|pmid=23891475}}</ref>

[[:Mevalonate pathway.png|350px|thumb|center|[[Mevalonate pathway]]]]

[[:Sterol synthesis.svg|thumb|center|350px|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.]]

IPP can be via alternative non-mevalonate pathway of isoprenoid biosynthesis , 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 pathway is many [[bacteria]], [[apicomplexa]]n [[protozoa]] such as [[malaria]] parasites, and the [[plastids]] of higher [[plants]].

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{{Reflist}}

{{Terpenoids}}

[[Category:]]