An Organometallic Isostere of an Amino Acid.

An organometallic complex that mimics an amino acid, also known as an amino acid isostere, can be synthesized from a functionalized bipyridine ligand and a fac-[Re(CO)3]+ center. The reaction of an achiral ligand and metal results in a racemic mixture of chiral-at-metal complexes. These metal species have amine and carboxy termini, a side chain type unit that can be varied, as well as the chiral metal that is analogous to the α carbon of an amino acid. The racemic mixtures can be separated into enantiomers by chiral chromatography, and the metal complexes can be incorporated into peptides by using solid-phase peptide synthesis.