The modification of amino acids and peptides with transition metal ions has been actively investigated for many decades, and the resultant compounds have been used for many applications ranging from inorganic therapeutics to catalysts for organic transformations.  Frequently, binding a metal ion or unit to a peptide either occurs via naturally occurring structure (such as the imidazole ring in histidine) or via a synthetically modified chelate.  In this talk, work on developing a transition metal based isostere of an amino acid will be discussed.  In these compounds, the metal ions are designed to behave as the alpha carbon positions, and the complexes exhibit several features that mimic the structure and chemistry of an amino acid.  In our approach, we are using the Re(CO)3 unit as the alpha carbon position along with an amine and carboxylic acid functionalized chelate.  The rhenium center provides several advantages for an amino acid isostere; in addition to incorporating a ligand with amine and acid functional groups, the metal center is both chiral and can be modified to mimic the side chains seen in normal amino acids.  This talk will focus on our recent results in our syntheses and use of these organometallic isostere compounds.

Design of an organometallic isostere of an amino acid

ACS Spring 2022

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