Main > PEPTIDES > CycloDimerization > Azide-Alkyne Reaction. > Cu Catalyzed Azide-Alkyne Reaction > Org.: USA. S (Mechanism) > NPLS Contents

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Copper-catalyzed azide-alkyne cycloaddition is a reaction that is used to cleanly, rapidly, and irreversibly join a range of substrates by means of 1,2,3-triazole linkages. A Org. s team has now determined previously unknown aspects of the reaction s detailed mechanism, such as the fact that two copper centers interact in the course of the process.

The researchers then employed this mechanistic information to develop a potentially important new application of the reaction--its use for head-to-tail dimerization of peptides. Cyclic peptides are of significant interest in biochemical research and drug discovery because they have been found to have promising biological properties. They have been used, for example, to create bioactive nanotubes and in vaccine research.

Authors carried out the mechanistic and synthetic studies. In the most notable peptide dimerization in their synthetic study, they cyclized two resin-bound 19-amino acid peptide sequences into a 38-residue cyclic peptide, 36 amino acids of which are in the ring.
"This level of ring size, chemical yield, and selectivity is unprecedented," Authors say. "Subsequent unpublished work suggests that the cyclic dimerization process is not limited to peptides but rather is general" for other compound types as well.






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