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

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.