Login / Signup

Enantioselective Recognition of Chiral Tryptophan with Achiral Glycine through the Strategy of Chirality Transfer.

Shanshan WuQiumin YeDatong WuYongxin TaoYong Kong
Published in: Analytical chemistry (2020)
Glycine (Gly), an achiral amino acid, has never been reported for enantioselective recognition owing to the absence of chiral sites. Herein, a facile strategy of chirality transfer is proposed to endow Gly with chirality. Optically active CuO, L-CuO, is first prepared, which can be used for the decoration of Gly through the formation of the Cu(Gly)2 complex. Successful chirality transfer from L-CuO to Gly is confirmed by circular dichroism (CD) spectra. The formation of the Cu(Gly)2 complex is further confirmed by Fourier transform infrared spectra and X-ray photoelectron spectroscopy. Next, the resultant L-CuO-Gly is used for chiral analysis of the isomers of tryptophan (Trp). Because of the higher affinity of L-CuO-Gly toward L-Trp than its isomer, the Trp isomers exhibit significant differences in their oxidation peak currents at the L-CuO-Gly-modified glassy carbon electrode (GCE) (IL-Trp/ID-Trp = 5.24). Finally, the practicability of the developed L-CuO-Gly/GCE is assessed, and the results indicate that it could be a reliable chiral sensor for the quantitative analysis of Trp isomers in nonracemic mixtures.
Keyphrases