Poly(ethylene glycol) methyl ether-block-poly(L-lactide) (PEG-PLLA) was emplyed to encapsulate 1,1'-Bi-2-naphthol (BINOL)-based enantioselective sensor (S)-1, to produce micelle sensor ML-S1. Amphiphilic property of PEG-PLLA enabled ML-S1 to be solvated into aqueous solutions. The micelle structure of ML-S1 was characterized through cryo-TEM. Fluorescence recognition of ML-S1 toward amino acids substrates was kinetically quenched by lowering the temperature. Upon quenching of furthur reactions, ML-S1 was able to recognize D-lysine chemoselectively and stereoselectively with strong fluorescence enhancement among 19 amino acids and their both enantiomers, and MD-R1 selectively recognize L-lysine. However, the corresponding organic sensor (S)-1 had rather complicated responses for Lysine in organic phase. Detailed NMR and Mass spectroscopic studies of organic core (S)-1 were carried out to give insights into the mechanism.

Micelle-encapsulated fluorescent probe: Chemoselective and enantioselective recognition of lysine in aqueous solution

2019 Fall National Meeting

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