Geranyl pyrophosphate
Structural formula | ||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
General | ||||||||||||||||
Surname | Geranyl pyrophosphate | |||||||||||||||
other names |
|
|||||||||||||||
Molecular formula |
|
|||||||||||||||
External identifiers / databases | ||||||||||||||||
|
||||||||||||||||
properties | ||||||||||||||||
Molar mass | 314.21 g mol −1 | |||||||||||||||
safety instructions | ||||||||||||||||
|
||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Geranyl pyrophosphate ( geranyl-PP or GPP for short ) is a biomolecule that can be found as a building block in terpene biosynthesis . From a chemical point of view, it is an ester of geraniol (an alcohol with two additional C = C double bonds ) and diphosphoric acid .
It is produced biosynthetically through a head-to-tail condensation ( nucleophilic substitution ) from the two isoprene units isopentenyl pyrophosphate and dimethylallyl pyrophosphate , with the help of a prenyl transferase ( geranyl transferase ).
Geranyl pyrophosphate is the starting compound of several thousand vegetable mono terpenes , which are mainly used as fragrances (essential oils) and pharmaceuticals (such as limonene ).
For example, α-pinene and β-pinene are synthesized from geranyl pyrophosphate by cyclization of linaloyl pyrophosphate , with subsequent rearrangement of a hydrogen atom.
In humans, geranyl pyrophosphate is used to synthesize squalene , an important precursor for cholesterol synthesis .
literature
- Albert L. Lehninger: Biochemistry , 2nd edition, Weinheim 1983, ISBN 3-527-25688-1 , p. 561.
Web links
Individual evidence
- ↑ Data sheet Geranyl pyrophosphate lithium salt from Sigma-Aldrich , accessed on July 24, 2018 ( PDF ).
- ↑ Voet & Voet, Biochemistry (second edition), Wiley & Son's, p. 696.
- ↑ Susan C. Trapp, Rodney B. Croteau: Genomic Organization of Plant Terpene Synthases and Molecular Evolutionary Implications ; Genetics , 2001, 158: 811-832; https://www.genetics.org/content/158/2/811 ; PMID 11404343 .