Electrochemical Chiral Recognition of Tryptophan Isomers Based on Nonionic Surfactant-Assisted Molecular Imprinting Sol-Gel Silica.

A new molecularly imprinted SiO2 (MISiO2) film on the surface of indium tin oxide (ITO) electrode was prepared by the sol-gel method and was then applied successfully in the electrochemical chiral recognition of tryptophan (Trp) isomers. Owing to the high chemical stability, excellent rigidity, and low cost, the resultant sol-gel SiO2 is a good matrix material for molecular imprinting. Nonionic surfactant cicosaethylene glycol hexadecyl ether (Brij58) arranged directionally on the surface of the hydrophobic ITO electrode possesses a large amount of oxygen-containing functional groups and may induce the accumulation of template molecules (L-Trp) on the surface of ITO, resulting in L-MISiO2/ITO after the removal of L-Trp templates by calcination. The characterizations of the L-MISiO2/ITO reveal that the L-Trp templates could be successfully removed from the matrix, producing complementary cavities within the L-MISiO2/ITO. The resultant L-MISiO2/ITO exhibits greatly higher affinity toward L-Trp than D-Trp due to the three-point interaction mechanism, and therefore it exhibits good chiral recognition ability for the Trp isomers. In addition, the as-prepared L-MISiO2/ITO or D-MISiO2/ITO (D-Trp as the templates) can predict the ratio of L- and D-isomers in racemic mixture. Last, the MISiO2 films exhibited quick binding kinetics and good recognition reproducibility.