Dimethylallyl pyrophosphate

Structural formula
General
Surname	Dimethylallyl pyrophosphate
other names	3,3-dimethylallyl pyrophosphate Dimethylallyl PP Dimethylallyl diphosphate DMAPP
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 358-72-5 PubChem 647 ChemSpider 627 DrugBank DB01785 Wikidata Q417398
properties
Molar mass	246.09 g mol −1 (protonated)
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 .

Dimethylallyl pyrophosphate ( dimethyl allyl PP or DMAPP for short , better: dimethyl allyl diphosphate DMADP ) 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 prenol (an alcohol with an additional C = C double bond ) and diphosphoric acid .

It is synthesized by the mevalonate biosynthetic pathway in the cytosol and is produced in the last step by the IPP isomerase from isopentenyl pyrophosphate (IPP). Feodor Lynen and Konrad Bloch received the Nobel Prize for Medicine in 1964 for their contribution to the discovery of the mevalonate biosynthetic pathway and the cholesterol metabolism .

In recent years, a second metabolic pathway to DMAPP and IPP has been discovered, the so-called MEP path ( methylerythritol phosphate path ). This metabolic pathway can be found in the plant plastids and in Plasmodium falciparum (the causative agent of malaria ). In addition to DMAPP, IPP is also created.

DMAPP and IPP are the starting substrates of around 30,000 terpenes known to date . In the human body, DMAPP and IPP are the basic substrates for the biosynthesis of hormones or cholesterol .

literature

Wikibooks: Isopentene pyrophosphate biosynthetic pathway based on acetyl-CoA and acetacetyl-CoA  - learning and teaching materials

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

Web links

Commons : Dimethylallyl 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. 150.