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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.

SUBMITTER: Chatkewitz LE

PROVIDER: S-EPMC5761740 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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

Chatkewitz Lindsay E LE Halonski John F JF Padilla Marshall S MS Young Douglas D DD

Bioorganic & medicinal chemistry letters 20171206 2

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 ...[more]

PMID: 29248298

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