Design and synthesis of chiral aminophosphonates: from biomimetic catalysis to phosphapeptides

-

Aminophosphonates are interesting compounds due to their analogy with amino acids and their derived peptides. They could interfere in biological mechanisms through their hydroxyphosphonyl group approximating the enzymatic reactive tetrahedral intermediate . We aim at creating a new basis for the investigation of aminophosphonates as amino acid mimics. In the research focus is the practical, efficient and enantioselective methodologies for the synthesis of aminophosphonates. Chiral ammonium salts that are p hase-transfer catalysts will be evaluated in preparation of such aminophosphonates. Phosphapeptides will be prepared by incorporating an aminophosphonate residue in short peptides, and will be studied using NMR together with computational chemistry as too ls to gain insight into changes in their conformations, dynamics and type of aggregates.