Metallic pseudopeptidic macrocycles. Study of molecular recognition processes of amino acids

Abstract

The aim of this work is the synthesis of the chiral pseudopeptidic macrocycle 5b and its use, together with analogue macrocycle 5a (Scheme 1) as ligands for Cu2+, in molecular recognition processes of amino acids. The two dinuclear complexes will be used as receptors in molecular recognition processes. The synthesis of the [2+2] pseudopeptidic macrocycle through a reductive amination is carried out by using an anionic template which places the four subunits in the right orientation for their union. The obtained product is characterized by ESI-MS and NMR. Copper complexes are prepared starting with the meta macrocycle and its para analogue. The resulting products are characterized by ESI MS. A comparative study of many amino acids and analogues behavior with the two macrocyclic complexes is carried out by UV-Vis spectrophotometry. After that, recognition tests are made with the two possible Malate isomers and association constants values are calculated for both isomers with macrocyclic copper complex.