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

Bioorg Med Chem Lett

Department of Chemistry, College of William & Mary, P.O. Box 8795, Williamsburg, VA 23187 USA. Electronic address:

Published: January 2018

AI Article Synopsis

  • The article discusses the significance of 1,3-dipolar cycloadditions of azides and alkynes in both biology and chemistry, emphasizing their widespread use.
  • It addresses the challenges posed by the need for a copper catalyst in these reactions and presents a solution through the development of a copper-free microwave-assisted process.
  • The researchers successfully synthesized various triazoles and applied this new method to bioconjugate a full-length protein using unnatural amino acids, marking a pioneering achievement in microwave-mediated protein chemistry.

Article 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.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5761740PMC
http://dx.doi.org/10.1016/j.bmcl.2017.12.007DOI Listing

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