6-Amino-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid has been designed to be incorporated in foldamers as a conformationally restricted fluorescent label. The carbostyril-based aromatic ε-amino acid was synthesized from o-nitrobenzaldehyde and dithylmalonate (DEM) by Knoevenagel and Stobbe-type condensation reaction. Like m-aminobenzoic acid, the amine and acid groups are separated by 120° for this ε-amino acid. This arrangement induces the resulting peptides to adopt a bent conformation, which makes them important building blocks for helical foldamers. The photophysical characterization of the carbostyril-based amino acid was performed by UV-vis absorption and fluorescence emission studies.
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