Synthesis of fluorescent d-amino acids with 4-acetamidobiphenyl and 4-N,N-dimethylamino-1,8-naphthalimido containing side chains

Add time:08/31/2019    Source:sciencedirect.com

We report the synthesis and fluorescence properties of two aromatic d-amino acids. The key step for the synthesis of (R)-2-amino-3-(4′-acetamido-[1,1′-biphenyl]-4-yl)propanoic acid was a Suzuki cross-coupling reaction between the pinacol diester of N-acetylphenylboronic acid and Fmoc-d-p-bromo-phenylalanine. The second amino acid, (R)-2-amino-4-(4′-N,N-dimethylamino-1,8-naphthalimido)butanoic acid [(R)-2-amino-4-DMNA-butanoic acid], was synthesized in four steps from 4-bromo-1,8-naphthalic anhydride. The amino acids were prepared in a form that could be readily incorporated into a peptide sequence by solid phase peptide synthesis using the Fmoc-strategy. Evaluation of the fluorescence properties of the biphenyl amino acid showed a maximum emission at 384 nm (excitation at 295 nm) while the naphthalimido amino acid showed a maximum emission at 545 nm (excitation at 450 nm).

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