Geranyl pyrophosphate

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Structural formula
Structural formula of geranyl pyrophosphate
General
Surname Geranyl pyrophosphate
other names
  • Geranyl PP
  • GPP
  • Geranyl diphosphate
Molecular formula
  • C 10 H 17 O 7 P 2 3−
  • C 10 H 20 O 7 P 2 (protonated)
External identifiers / databases
CAS number
  • 763-10-0
  • 21141-43-5 (lithium salt)
PubChem 445995
ChemSpider 393471
DrugBank DB02552
Wikidata Q418125
properties
Molar mass 314.21 g mol −1
safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
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 ).

The condensation reaction of dimethylallyl (left) and isopentenylpyrophosphate (right) to geranylpyrophosphate is the Geranyltransferase catalyzed.

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.

Pinene biosynthesis

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

Commons : Geranyl Pyrophosphate  - Collection of pictures, videos, and audio files

Individual evidence

  1. Data sheet Geranyl pyrophosphate lithium salt from Sigma-Aldrich , accessed on July 24, 2018 ( PDF ).
  2. Voet & Voet, Biochemistry (second edition), Wiley & Son's, p. 696.
  3. 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 .