Investigation of copper-free alkyne/azide 1,3-dipolar cycloadditions using microwave irradiation

Abstract

The prevalence of 1,3-dipolar cycloadditions of azides and alkynes within both biology and chemistry highlights the utility of these reactions. However, the use of a copper catalyst can be prohibitive to some applications. Consequently, we have optimized a copper-free microwave-assisted reaction to alleviate the necessity for the copper catalyst. A small array of triazoles was prepared to examine the scope of this approach, and the methodology was translated to a protein context through the use of unnatural amino acids to demonstrate one of the first microwave-mediated bioconjugations involving a full length protein.

Keywords: Alkyne; Azide; Bioconjugation; Microwave irradiation; Unnatural amino acid.