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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]

References

^ http://pubs.rsc.org/en/Content/ArticleLanding/2014/NP/C3NP70124G#!divAbstract
^ 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
^ 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.

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English Journal

Molecular cloning of mevalonate pathway genes from Taraxacum brevicorniculatum and functional characterisation of the key enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase.

van Deenen N, Bachmann AL, Schmidt T, Schaller H, Sand J, Prüfer D, Schulze Gronover C.SourceInstitut für Biologie und Biotechnologie der Pflanzen, Westfälische Wilhelms-Universität Münster, Hindenburgplatz 55, 48143, Münster, Germany.
Molecular biology reports.Mol Biol Rep.2012 Apr;39(4):4337-49. Epub 2011 Aug 11.
Taraxacum brevicorniculatum is known to produce high quality rubber. The biosynthesis of rubber is dependent on isopentenyl pyrophosphate (IPP) precursors derived from the mevalonate (MVA) pathway. The cDNA sequences of seven MVA pathway genes from latex of T. brevicorniculatum were isolated, includ
PMID 21833516

Nonradioactive assay for detecting isoprenyl diphosphate synthase activity in crude plant extracts using liquid chromatography coupled with tandem mass spectrometry.

Nagel R, Gershenzon J, Schmidt A.SourceDepartment of Biochemistry, Max Planck Institute for Chemical Ecology, Beutenberg Campus, D-07745 Jena, Germany.
Analytical biochemistry.Anal Biochem.2012 Mar 1;422(1):33-8. Epub 2012 Jan 3.
Terpenoids form the largest class of plant metabolites involved in primary and secondary metabolism. Isoprenyl diphosphate synthases (IDSs) catalyze the condensation of the C(5) terpenoid building blocks, isopentenyl diphosphate and dimethylallyl diphosphate, to form geranyl diphosphate (C(10)), far
PMID 22266300

Japanese Journal

Mutant deletions in Escherichia coli affect the cellular levels of undecaprenyl phosphate and undecaprenyl diphosphate

Saito Yuichiro,Ishikawa Tatsuya,Murakami Marie [他]
Journal of biological macromolecules 13(3), 86-91, 2013-12
NAID 40020070892

選択的固相抽出法を用いるイソペンテニルピロリン酸とジメチルアリルピロリン酸との合量のLC/MS/MS定量

佐藤友美,桑原直子,中川沙織,大和進
分析化学 = Japan analyst 62(8), 731-735, 2013-08-05
NAID 10031178772

「イソペンテニル二リン酸」

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