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Synthesis of metal binding artificial amino acids

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2014
Eşan, Gözde
A large variety of peptides with different physical and chemical properties can be acquired by using different amino acids. Through chemical peptide synthesis, utilizing unnatural synthetic amino acids beside 21 natural amino acids, divergent peptides can also be obtained easily. Specifically amino acid and peptide conjugates of metals have received considerable attention due to their important role in many biological processes with unique structural properties. Moreover, it is well known that some metal ions are essential for living organisms and important for biochemical reactions as well as metal-amino acids and peptide complexes. The target of this project is to obtain metal binding artificial amino acids and to use these artificial amino acids in pre-designed peptide sequence. For this purpose, initially a bipyridine and pyridine bistriazole amino acid derivatives that can coordinate to a wide variety of metal ions were tried to be synthesized using Stille coupling reactions and Huisgen cycloaddition reactions, respectively. Consequently, only diamine derivative of pyridine bistriazole could be synthesized. After that synthesis, tetrapeptide including lysine (K), phenylalanine (F) and glutamic acid (E) was coupled to the two side of diamine derivative. Having the parallel β-hairpin structure and the metal binding units in the middle of this sequence owing to triazoles could give a chance metal transport and release in biological systems.