Utilizing Synthetic Tools to Address Biological Issues

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Padilla, Marshall Scott
Biochemistry; Molecular Biology; Organic Chemistry; Other Chemistry
thesis / dissertation description
With the advent of chemoselective reactions and unnatural amino acids (UAAs), the fields of molecular biology and organic synthesis are merging. Researchers are developing synthetic tools and producing small molecules that are able to affect and investigate large biomolecules and complex living systems. This thesis undertakes a survey of synthetic techniques to develop novel tools that can be employed to address a variety of relevant biological questions. Specifically, we are investigating alternatives and improvements to caging groups, including photoreversible azobenzene UAAs and an UAA caging group possessing a bioorthogonal handle. Also, we are developing a novel system to undergo copper-free 1,3-dipolar cycloadditions, utilizing microwave irradiation. Adapting this methodology, we showcase the first transition and metal free bioconjugations utilizing microwave irradiation through CoolMate technology. Finally, we are examining a method to insert a highly reactive selenocysteine amino acid into proteins via the integration of a caging group and unnatural amino acid technologies.