Farnesyl pyrophosphate

Structural formula
General
Surname	Farnesyl pyrophosphate
other names	FPP; (2 E , 6 E ) Farnesyl Diphosphate;
Molecular formula	C 15 H 25 O 7 P 2 3− ; C 15 H 28 O 7 P 2 (protonated);
Brief description	white solid (ammonium salt)
External identifiers / databases
PubChem	445713
ChemSpider	393270
DrugBank	DB07780
Wikidata	Q2699676
properties
Molar mass	382.32 g mol −1
Physical state	solid (ammonium salt)
safety instructions
GHS hazard labeling ; no classification available
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 .

Farnesyl pyrophosphate is a chemical compound from the group of pyrophosphates and contains three isoprene units . From a chemical point of view, it is an ester of farnesol (an alcohol with three additional C = C double bonds ) and diphosphoric acid .

Occurrence

Farnesyl pyrophosphate is an important intermediate in the biosynthesis of more complex sesquiterpenes , higher terpenoids, and steroids . It arises, for example, in the initial part of the cholesterol biosynthetic pathway and is also required for the formation of ubiquinone and dolichol phosphate . It plays an important role in the post-translational modification of Ras proteins . Mutated forms of Ras are associated with human cancers and are therefore investigated in cancer research. It is involved in the farnesylation of proteins.

It is formed from geranyl pyrophosphate through the addition of another isoprene unit.

In addition to the mainly occurring trans - trans isomer, the cis - cis isomer could also be detected in some plants (such as tomatoes) .

literature

Albert L. Lehninger: Biochemistry , 2nd edition, Weinheim 1983, ISBN 3-527-25688-1 , p. 561.

Web links

Commons : Farnesyl Pyrophosphate - Collection of Images, Videos, and Audio Files

Individual evidence

↑ ^a ^b ^c ^d data sheet trans, trans-Farnesyl pyrophosphate ammonium salt, ≥95.0% (HPLC) from Sigma-Aldrich , accessed on June 21, 2015 ( PDF ).
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Georg Löffler: Basic knowledge of biochemistry with pathobiochemistry . Springer-Verlag, 2013, ISBN 978-3-662-05984-5 , pp. 208 ( limited preview in Google Book search).
↑ Gerd-Joachim Krauss, Dietrich H. Nies: Ecological Biochemistry Environmental and Interspecies Interactions . John Wiley & Sons, 2014, ISBN 978-3-527-68600-1 ( limited preview in Google Book Search).
^ Lew Mander: Comprehensive Natural Products II: Chemistry and Biology 10 Volume Set . Newnes, 2010, ISBN 0-08-045382-1 , pp. 619 ( limited preview in Google Book search).

[Sigma-1] ta sheet trans, trans-Farnesyl pyrophosphate ammonium salt, ≥95.0% (HPLC) from Sigma-Aldrich , accessed on June 21, 2015 ( PDF ).

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Georg_Löffler-3] Georg Löffler: Basic knowledge of biochemistry with pathobiochemistry . Springer-Verlag, 2013, ISBN 978-3-662-05984-5 , pp. 208 ( limited preview in Google Book search).

[Gerd-Joachim_Krauss,_Dietrich_H._Nies-4] Gerd-Joachim Krauss, Dietrich H. Nies: Ecological Biochemistry Environmental and Interspecies Interactions . John Wiley & Sons, 2014, ISBN 978-3-527-68600-1 ( limited preview in Google Book Search).

[Lew_Mander-5] Lew Mander: Comprehensive Natural Products II: Chemistry and Biology 10 Volume Set . Newnes, 2010, ISBN 0-08-045382-1 , pp. 619 ( limited preview in Google Book search).