Design and Synthesis of Fluorescent Amino Acids: Novel Tools for Biological Imaging

The PhD project aims to develop novel fluorescent amino acids with clearly defined properties that can act as imaging probes for molecular and cellular biological applications. In particular, we aim to generate an understanding of how molecular structure affects properties such as quantum yield and emission wavelength. Several classes of novel N-heterocycle-derived amino acids will be prepared from easily accessible enone derivatives using a range of cycloaddition reactions. Lead compounds from each class of amino acid that show sharp fluorescence, high quantum yields and interesting solvatochromatic properties will be further investigated as probes for biological imaging. These will be incorporated into short cell-penetrating peptides (e.g. FluAA-Val-Pro-Thr-Leu-Lys) using solid phase peptide synthesis, incubated with various cell lines and analysed using confocal fluorescent microscopy.