Isopentenyl pyrophosphate

Isopentenyl pyrophosphate
Names


IUPAC name (hydroxy-(3-methylbut-3-enoxy) phosphoryl)oxyphosphonic acid
Identifiers
CAS Number	358-71-4^Y
ChEBI	CHEBI:128769^Y
ChemSpider	13115335^Y
Jmol interactive 3D	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^Y Key: NUHSROFQTUXZQQ-UHFFFAOYSA-K^Y 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).
Y verify (what is ^YN ?)
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]

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.

Cholesterol and steroid metabolic intermediates

Mevalonate pathway

to HMG-CoA	Acetyl-CoA Acetoacetyl-CoA HMG-CoA

Ketone bodies	Acetone Acetoacetic acid β-Hydroxybutyric acid

to DMAPP	Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate

Geranyl-	Geranyl pyrophosphate Geranylgeranyl pyrophosphate

Carotenoid	Prephytoene diphosphate Phytoene

Non-mevalonate pathway

To Cholesterol

From Cholesterol
(to steroids)

Steroid hormones

See here instead.

Nonhuman

Phytosterols	Stigmasterol Brassicasterol

Ergosterols	Ergosterol Ergocalciferol

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Isopentenyl pyrophosphate

See also

References