Highly enantioselective fluorescent sensor for chiral recognition of amino acid derivatives

A highly enantioselective fluorescent sensor, containing benzylaminomethyl groups at 3,3'-position of 1,1'-bi-2-naphthol (BINOL), has been used to conduct the chiral recognition of cc-amino acid derivatives. It is observed that one enantiomer of N-Boc-proline can increase the fluorescence intensity of the binaphthyl fluorophores by over 57-fold, while the other enantiomer can cause only sixfold fluorescence enhancement. Such unusually highly enantioselective response demonstrates that this sensor is potentially useful in the enantioselective recognition of amino acid derivatives. (C) 2009 Elsevier Ltd. All rights reserved.