“Click” chemistry refers to reactions that can combine two chemical components into a single complex in a fast and reliable manner. The most popular “Click” reaction is the Cu(I) – catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) process introduced independently by K. B. Sharpless and Meldal in 2002. This chemistry is widely used in bioconjugation and related biological applications. In the following presentation, we will describe our efforts toward the development of sterically caged copper catalyst that are active inside biological environments. Our studies showed that dinuclear aza cryptand copper complexes 1b and 2b can catalyze CuAAC reaction between benzyl azide and phenyl acetylene in aqueous conditions, even in the presence of the thiol-containing biomolecules glutathione and cysteine. A notable result is that the dicopper cryptand complexes gave about a three-fold higher yield compared to that by the copper salt CuSO4. This work suggests that “substrate gating” might be a useful strategy in the design of biocompatible catalysts that can avoid deactivation by biological nucleophiles inside living cells.

Copper cryptand complexes as catalysts for CuAAC click reactions and their prospects for in vivo applications

255th National Meeting (2018)

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