Isopentenyl pyrophosphate

Isopentenyl pyrophosphate
IUPAC name (hydroxy-(3-methylbut-3-enoxy) phosphoryl)oxyphosphonic acid
Identifiers
CAS number	358-71-4 Y
PubChem	15983957
ChemSpider	13115335 Y
MeSH	isopentenyl+pyrophosphate
ChEBI	CHEBI:128769 Y
Jmol-3D images	Image 1
SMILES CC(=C)CCOP(=O)([O-])OP(=O)([O-])[O-]
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
Properties
Molecular formula	C5H12O7P2
Molar mass	246.092
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Isopentenyl pyrophosphate (IPP) is an intermediate in the classical, HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. IPP is formed from acetyl-CoA via mevalonic acid. IPP can then be isomerized to dimethylallyl pyrophosphate by the enzyme isopentenyl pyrophosphate isomerase.

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.

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.

See also

• Dimethylallyltranstransferase