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45503-G4
Photoactivated 1,3-Dipolar Cycloaddition: Scope and Applications

Qing Lin, State University of New York at Buffalo

During the past year, we have thoroughly investigated the scope of the photoactivated, nitrile imine mediated 1,3-dipolar cycloaddition reaction, including solvent compatibility, functional group tolerance, and photoactivation wavelength tunability.  We showed that highly functionalized pyrazolines can be readily prepared via this photoactivated cycloaddition reaction.  Additionally, we showed that this chemistry serves as a bioorthogonal chemistry in the labeling of the tetrazole-containing proteins in biological media as well as the alkene-containing proteins in live bacterial cells.  Finally, we demonstrated that this chemistry can be applied in an intramolecular fashion to cross-link peptide sidechains to form fluorescent, "stapled" peptide helices.

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