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Synthesis of a Novel Unnatural Amino Acid for Protein Incorporation and Click Mediated Conjugation
Farley, Christopher A
Farley, Christopher A
Abstract
Unnatural amino acids (UAAs) contain side chains, or R groups, that are not found in the 20 canonical amino acids. These noncanonical groups afford the capability to incorporate powerful chemical capabilities in proteins that are ordinarily unavailable with the naturally-occurring amino acids. Among the most useful moieties to incorporate into proteins are functional groups that can undergo Huisgen [3+2] cycloadditions, or “click,” reactions. This reaction occurs between azides and alkynes, and its mild conditions and high regioselectivity and reactivity make it an ideal process for bioconjugation. Photoreactivity is another useful characteristic that can be conferred to UAAs. Photolabile caging groups can inhibit the function of a protein until brief irradiation with UV light induces an intramolecular rearrangement and its displacement, reestablishing normal function. In this thesis, we propose a synthesis to incorporate both of these moieties into a single UAA.
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2014-04-01
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Chemistry