Bioorthogonal chemistry allows further exploration of the intricacy of life through the development of highly selective reactions that occur reliably, even in a complex biological environment. Past work in the Weaver group developed a reaction system that utilizes an iridium-based photocatalyst, a cycloalkene, and blue light to transform light energy into molecular strain energy within the cycloalkene. The strained cycloalkene can then conjugate with an azide via a “click” reaction. This reaction is highly selective, fast, and only occurs in the presence of blue light, priming it for use for biological tagging and probing. Both of my aims (<i>infra vide</i>) increase the function of this novel reaction system by 1) modifying the cycloalkene to expand its use in biological systems, and 2) further probing of the reaction mechanism, which will allow the technology to reach its full scientific potential. More specifically, I am attempting to modify the structure of the cycloalkenes such that it may be able to conjugate with the azide without photocatalyst. Potential structural candidates were selected based on our hypothesis that the primary hinderance of the direct photochemical reaction is the rate of inter-system crossing was too slow. My second objective is to modify the structure of the cycloalkene such that it can be readily synthesized, conjugated to biological tools easily, and maintain ideal physiochemical properties to be used in biological systems. Continued investigation of this technology is expected to expand our knowledge of this photochemical reaction and refine the technology such that it can be used in diverse applications.

Adaptation of strain loadable alkenes for biological uses

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