Non-proteinogenic amino acids, or amino acids which differ in the side chain structure from the 23 amino acids commonly found in proteins, have played significant roles in the development of modern society. These seemingly simple molecules have driven advances in agriculture, food processing, materials science, and pharmaceutical development. One of the most exciting and promising areas of this research has been the use of structurally diverse amino acids for the selective modification of peptides through amber codon suppression. This allows these unique molecules to act as probes for understanding the role and mechanism of various biologically important peptides or to increase the potency of various therapeutic peptides. These modifications may prove ideal for the treatment of various diseases due to the potential for fewer side effects compared to current small molecule pharmaceutical agents. Despite developments in the study and application of these vital biological molecules, very few advances have been made in the fundamental science of their synthesis. Therefore, with this in mind the preparation of a series of Ni(II) complexed Schiff’s Base derived nucleophilic glycine equivalents will be described including the synthesis of the required ligands and 2-aminobenzophenones or 2-aminobenzaldehydes. Additionally, these complexes will be evaluated regarding their utility for the preparation of non-proteinogenic a-amino acids. Two methods of homologation, alkyl halide alkylation and Michael Addition Reactions, will be utilized to evaluate the reactivity of these Ni(II) complexed glycine equivalents compared to previous generations that have been introduced through competitive reaction approaches.

Preparation and reactivity comparison of a series of Ni(II) complexed nucleophilic glycine equivalents

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