Prenylation

Two different presentations of the prenyl group (= prenyl radical) with the empirical formula C ₅ H ₉ using the example of prenyl bromide. The prenyl group is marked in blue . - The IUPAC name of the prenyl group is 3-methylbut-2-enyl.

Gene Ontology
Parent
Lipoprotein biosynthesis
QuickGO

The prenylation or isoprenylation is a biological process, a so-called post-translational modification , ie a change of proteins after translation . This process is used to achieve the full functionality of the protein. A terpene residue (e.g. farnesol by farnesylation from farnesyl pyrophosphate , geranylgeraniol by geranylgeranylation from geranyl pyrophosphate , dolichol from dolichol pyrophosphate ) is covalently attached to the cysteinyl radicals of proteins. This creates a large hydrophobic group, which allows the protein stable in the membrane to anchor . The result of prenylation is a lipoprotein .

Important prenylable proteins are ras from the protein family of small GTPases , molecular switches that are important for cell division and growth, but also play a key role in the development of many tumors . Isoprenylation inhibitors , such as. B. Farnesol as an inhibitor of farnesyl transferase and thus farnesylation , appear as possible active ingredients against cancer.

Individual evidence

↑ Jonathan Clayden, Nick Greeves, Stuart Warren, Peter Wothers: Organic Chemistry , Oxford University Press, 2001, ISBN 978-0-19-850346-0 , p. 417.
^ Albert Gossauer: Structure and reactivity of biomolecules , Verlag Helvetica Chimica Acta, Zurich 2006, ISBN 978-3-906390-29-1 , p. 100.
^ Eastman RT, Buckner FS, Yokoyama K, Gelb MH, Van Voorhis WC: Thematic review series: lipid posttranslational modifications. Fighting parasitic disease by blocking protein farnesylation . In: J. Lipid Res . 47, No. 2, February 2006, pp. 233-240. doi : 10.1194 / jlr.R500016-JLR200 . PMID 16339110 .
^ Basso AD, Kirschmeier P, Bishop WR: Lipid posttranslational modifications. Farnesyl transferase inhibitors . In: J. Lipid Res . 47, No. 1, January 2006, pp. 15-31. doi : 10.1194 / jlr.R500012-JLR200 . PMID 16278491 .

[Clayden-1] Jonathan Clayden, Nick Greeves, Stuart Warren, Peter Wothers: Organic Chemistry , Oxford University Press, 2001, ISBN 978-0-19-850346-0 , p. 417.

[Gossauer-2] Albert Gossauer: Structure and reactivity of biomolecules , Verlag Helvetica Chimica Acta, Zurich 2006, ISBN 978-3-906390-29-1 , p. 100.

[3] Eastman RT, Buckner FS, Yokoyama K, Gelb MH, Van Voorhis WC: Thematic review series: lipid posttranslational modifications. Fighting parasitic disease by blocking protein farnesylation . In: J. Lipid Res . 47, No. 2, February 2006, pp. 233-240. doi : 10.1194 / jlr.R500016-JLR200 . PMID 16339110 .

[4] Basso AD, Kirschmeier P, Bishop WR: Lipid posttranslational modifications. Farnesyl transferase inhibitors . In: J. Lipid Res . 47, No. 1, January 2006, pp. 15-31. doi : 10.1194 / jlr.R500012-JLR200 . PMID 16278491 .