Probing unencoded biomolecules such as carbohydrates in their native environments poses a complex challenge to scientists. The Bertozzi lab pioneered several novel bioorthogonal reactions to visualize carbohydrates in living systems. The most promising strategy, strain-promoted azide-alkyne cycloadditions (SPAAC), is a particularly useful class of bioorthogonal reactions that are relatively fast while bypassing toxic metal catalysts. However, methods to access strained alkynes are often laborious and result in compounds with low stability. In this research, oxygen-containing and nitrogen-containing cyclic alkyne targets were pursued using the Nicholas reaction as the key ring closure step, a strategy which simplifies the often challenging installation of the strained alkyne moiety and allows for the inclusion of diverse heteroatoms. Current research is focused on evaluating a variety of oxidative decomplexation methods for the final cobalt removal step using CAN, NMO, Fe(NO3)3 and Me3NO.
A poster deriving from independent lab research with Kevin Shea, Professor of Chemistry.