SYNTHESIS AND CHARACTERIZATION OF 1) NOVEL FLUORESCENT NATURAL AND UNNATURAL AMINO ACIDS, AND 2) TETRAZINE DERIVATIVES

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Doctor of Philosophy (PhD)
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Chemistry
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Chemistry
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2023
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Micikas, Robert, John
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Abstract

Fluorescent amino acids (FAAs) offer significant advantages over fluorescent proteins in applications where the fluorophore size needs to be limited or minimized. A long-sought goal in biological spectroscopy/microcopy is to develop visible FAAs by modifying the indole ring of tryptophan. In Chapter 1 of this thesis, I discuss the investigation of the absorption spectra of a library of 4-substituted indoles and find that the frequency of the absorption maximum correlates linearly with the global electrophilicity index of the substituent. In Chapter 2, a scalable synthesis of Fmoc-protected blue fluorescent amino acid, L-4-cyanotryptophan (W4CN), exploiting an enantioselective phase-transfer catalyzed alkylation is presented. Finally, in Chapter 3, Large-Scale Synthesis and Assessment of the Potential Thermal Hazards of 3,6-dichlorotetrazine (DCT) will be discussed.

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Smith, Amos, B
Date of degree
2023
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