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Unsaturated Amino Acids

Matthias Junkers

Recent developments in Chemical Biology research have increased the demand of amino acid building blocks with unsaturated side chains. Alkyne moieties can be used in bioorthogonal synthesis strategies to form hybrid structures, introduce chemical probes into biomolecules, or link large fragments with each other. The most prominent technique relies on the Huisgen dipolar cycloaddition reaction between an azide and an alkyne.

Olefin moieties open amino acids and peptides to metathesis reactions and a full range of other bioorthogonal synthesis routes. Olefin metathesis is a key to the production of hydrocarbon stapled peptides.1 Stapled peptides are currently in discussion as a new class of superpotent drugs or magical bullets promising to make peptide α-helices more potent and cell permeable by locking them in the most active conformation.2

References

1.
Walensky LD. 2004. Activation of Apoptosis in Vivo by a Hydrocarbon-Stapled BH3 Helix. Science. 305(5689):1466-1470. http://dx.doi.org/10.1126/science.1099191
2.
Kritzer JA. 2010. Magic bullets in nature's arsenal. Nat Chem Biol. 6(8):566-567. http://dx.doi.org/10.1038/nchembio.407