Chemically Fuelled Deracemization of Amino Acids

Systems that work out-of-equilibrium are common in nature, living organisms are the most striking example of that. Chemists are trying to mimic living organisms because of the multitude of properties that might be implemented in synthetic systems. With this project we want to realize an out-of-equilibrium system in which chemical fuel consumption is used to shift the equilibrium between L- and D-amino acids The system presented is composed of a starting equilibrium between the enantiomers of an amino acid or a derivative. From that starting point we create an ester, mediated by a chemical fuel able to convert a carboxylic acid into an ester. The use of an enantiomerically pure chiral fuel would lead to the formation of diastereomeric esters and, consequently, the equilibrium would shift in favour of the more stable one under conditions where racemization of the stereocenter of the amino acid takes place. Ester hydrolysis induced by the presence of a chiral catalyst, drives our system to the original amino acids but enriched in one of the enantiomers. This enantiomeric enrichment can only be maintained as long as ester formation and hydrolysis occur. In this thesis, the attention was focused on finding the best molecules and conditions to implement the system described above.