Jyotirmoy Maity, D. Honcharenko, R. Strömberg
Aug 12, 2015
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Influential Citations
8
Citations
Journal
Tetrahedron Letters
Abstract
Abstract 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).