Synthesis of Novel Optically Active α-Amino Acids via Glaser and Mannich Reactions, and the Development and Study of Short Peptides Based on Them as Chiral Organocatalysts

The project focuses on developing methods for the synthesis of enantiomerically enriched unsaturated (S)-α-amino acids with diverse substituents in the side chain and investigating square planar nickel complexes as synthons in various named chemical reactions. The primary objectives include synthesizing square planar complexes of Ni(II) Schiff bases derived from (S)-propargylglycine and dehydroalanine with a chiral auxiliary, (S)-2-N-[N'-benzylprolyl] aminobenzophenone, and studying C-α-alkylation, addition reactions, Glaser coupling, Mannich reactions, and trifluoromethylation of the terminal acetylene bonds of the α-amino acid fragment within the complexes. The project aims to develop peptides based on the synthesized amino acids and evaluate these peptides as organocatalysts in model reactions. The project will investigate reaction mechanisms using DFT calculations to gain a detailed understanding of the reaction kinetics. Furthermore, the synthesized non-protein amino acids will undergo biological screening and computer modeling to study the interaction mechanisms between the substrates and enzymes. This comprehensive approach aims to enhance the understanding and application of these novel amino acids and their complexes in synthetic and biological chemistry.