'Naked-eye' enantioselective chemosensors for N-protected amino acid anions bearing thiourea units.

Four linear thiourea anion receptors (1-3) derived from simple amino acid have been synthesized and their bonding properties with various chiral N-protected amino acid anions were examined by using UV-vis and fluorescence titration experiments. Receptors 1a, 2, and 3 exhibit excellent enantioselective recognition abilities towards N-Boc-protected alanine anion in the UV-vis spectra, obvious difference in the color of solution indicate that the enantiomers of N-Boc-alanine anion could be distinguished by naked eye directly. Receptor 1a is also found to carry out enantioselective fluorescent recognition of the N-acetyl-glutamate. (1)H NMR experiments suggest that hydrogen-bonding interaction between the host and guest is the main factor in the recognition process. (c) 2008 Wiley-Liss, Inc.