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Playing into our hands: The achiral bipyridine amino acid fluorenylmethyoxlcarbonyl 5-amino-3-oxapentanoic acid (Fmoc-O1PenBpy-OH) has been used for the solid-phase synthesis of metallopeptides. Circular dichroism, molecular modeling, and NMR spectroscopic studies show that the chirality of the resulting metal complexes in aqueous solution is determined, and can thus be controlled, by the stereochemistry of one proline residue in the loop between the two coordinating O1PenBpy residues.