A Novel Approach to Bioorthogonal Reactions
Mentor:Vincent Lavallo, Assistant Professor of Chemistry, University of California, Riverside
Click chemistry has been shown to facilitate a cycloaddition reaction that can have excellent outcomes within biological organisms. Organic azides attached to fluorescent probes undergo click reactions with alkenes in the organism to allow in vivo labeling and in depth studies of biomolecules. By utilizing a copper catalyst, chemists have succeeded in synthesizing triazoles, the product of click reactions; but the consequences have been disastrous, since trace amounts of copper is toxic to cells. In order to safely carry out click chemistry in vivo and preserve the bioorthogonal nature of the reaction, a specific triazole has to be synthesized such that it does not interrupt any biological processes and that it is fast-forming and water stable. The triazole in question has in fact been synthesized, however the ultimate goal of this project is to fully quantify the reaction rate whilst further exploring other bioorthogonal attributes. An icosahedral “carborane” with a linear azide performs this rather interesting cycloaddition with the olefin, norbornene, to give, in high yield and purity, the unique triazole.