Isopentenyl pyrophosphate

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Structural formula
Structural formula of isopentenyl pyrophosphate
General
Surname Isopentenyl pyrophosphate
other names
  • Isopentenyl diphosphate
  • Δ 2 -isopentenyl pyrophosphate
  • IPP
Molecular formula
  • C 5 H 9 O 7 P 2 3−
  • C 5 H 12 O 7 P 2 (protonated)
External identifiers / databases
CAS number 358-71-4
PubChem 1195
ChemSpider 1158
DrugBank DB04714
Wikidata Q417403
properties
Molar mass 246.09 g mol −1
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Isopentenyl pyrophosphate ( isopentenyl-PP or IPP for short ) is a biomolecule that can be found as a basic building block in terpene biosynthesis . From a chemical point of view, it is an ester of isoprenol (an alcohol with an additional C = C double bond ) and diphosphoric acid .

It is produced biosynthetically via the mevalonate route and via the methylerythritol phosphate route . These synthetic routes are described in more detail under the isomer of IPP, dimethylallyl pyrophosphate , cholesterol biosynthesis and the methylerythritol phosphate route.

Isopentenyl pyrophosphate is used in organisms for the biosynthesis of terpenes and terpenoids or can be converted to dimethylallyl pyrophosphate by the IPP isomerase . Farnesyl pyrophosphate can also be produced from 2 units of IPP and a dimethylallyl pyrophosphate .

The amino group of the nucleoside adenosine is converted to N 6 -isopentenyladenosine by means of the tRNA isopentenyl transferase with isopentenyl pyrophosphate .

literature

  • Albert L. Lehninger: Biochemistry , 2nd edition, Weinheim 1983, ISBN 3-527-25688-1 , p. 560.

Web links

Commons : Isopentenyl Pyrophosphate  - Collection of Pictures, Videos and Audio Files

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ↑ Horn, Lindenmeier, Moc, Grillhösl, Berghold, Schneider, Münster: Biochemie des Menschen (2nd edition). P. 149.
  3. ↑ N. Rosenbaum, ML Gefter: Δ 2 -isopentenylpyrophosphate: transfer ribonucleic acid Δ 2 -isopentenyltransferase from Escherichia coli. Purification and properties of the enzyme. In: Journal of Biological Chemistry . Volume 247, Number 18, September 1972, pp. 5675-5680, PMID 4341485 .