Isopentenyl pyrophosphate

Isopentenyl pyrophosphate

Names
IUPAC name (Hydroxy-(3-methylbut-3-enoxy) phosphoryl)oxyphosphonic acid
Identifiers
CAS Number	358-71-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:128769 Y
ChemSpider	1158 Y
MeSH	isopentenyl+pyrophosphate
PubChem CID	1195
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) Y[Pubchem] Key: NUHSROFQTUXZQQ-UHFFFAOYSA-N Y[Pubchem]
SMILES CC(=C)CCOP(=O)(O)OP(=O)(O)O
Properties
Chemical formula	C5H12O7P2
Molar mass	246.092 g·mol−1
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 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 DMAPP, are used by organisms in the biosynthesis of terpenes and terpenoids.

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.^[2]

IPP can be synthesised via an alternative non-mevalonate pathway of isoprenoid precursor biosynthesis, the MEP pathway, 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 MEP pathway is present in many bacteria, apicomplexan protozoa such as malaria parasites, and in the plastids of higher plants.^[3]

See also

• Dimethylallyltranstransferase

References