D-Serine

Binaphthyl-based chiral fluorescent probes (S)-/(R)-1 featuring a 2-methylthiophenimide unit were designed and synthesized.The fluorescent response to enantiomer pairs of amino acids revealed that (S)- and (R)-enantimer of the probe had chiral bias to L- and D-amino acids, resp.The compound (S)-1 showed outstanding enantioselective fluorescence enhancement toward 10 amino acids (Asn, Glu, Val, Leu, Met, Ser, Gln, Arg, Phe and Ala) in both solvents of EtOH/H2O and DMSO/H2O at the condition of pH 7.5.Extremely high enantiomeric fluorescence enhancement ratio (ef, [IL-I0]/[ID-I0]) were obtained for Asn (646.2), Glu (318.9), Val (255.6), Leu (252.4), Thr (223.9) in EtOH/H2O, and the ef values to Val, Ala, Ser, Glu, Arg, Gln were all larger than 20 in DMSO/H2O.Chiral fluorescent imaging of the four amino acids (Ser, Val, Arg and Gln) were obtained in both living cells and zebrafishes via the probe (R)-1, which provides a new concept for the diagnosis and treatment of diseases associated with amino acid racemization.Results of 1H NMR and HRMS revealed the enantioselective fluorescence enhancement mechanism.

Enantioselective recognition is crucial in pharmaceutical anal. and life sciences but remains a significant challenge.Herein, we constructed two chiral probes named (1R, 2R)-CHDA-2TPE and (1S, 2S)-CHDA-2TPE, which exhibit typical aggregation-induced emission (AIE) properties.The chiral probes show high enantioselectivity to 11 kinds of chiral reagents.Notably, the fluorescence intensity ratio of the probe with L- and D-glutamic acid was up to 88.8.The ¹H NMR titration results suggested that the hydrogen bond is response for the recognition.These findings implied that the synthesized probes are promising candidates for analyzing chiral compounds