Development of a chiral electrochemical sensor based on copper-amino acid mercaptide nanorods for enantioselective discrimination of tryptophan enantiomers

Abstract

Chirality is an important property of nature and it regulates fundamental phenomena in nature and organisms. Here, we develop a chiral electrochemical sensor based on copper-amino acid mercaptide nanorods (L-CuCys NRs) to discriminate tryptophan (Trp) isomers. The chiral L-CuCys NRs are prepared in alkaline solution based on the facile coordination reaction between the sulfhydryl groups of L-Cys and copper ions. Since the stability constant (K) of L-CuCys NRs with L-Trp (752) are much higher than that of L-CuCys NRs with D-Trp (242), the cross-linking bonds between L-CuCys NRs and L-Trp are more stable than those between L-CuCys NRs and D-Trp. Consequently, this electrochemical sensor can selectively recognize the Trp isomers with an enantiomeric electrochemical difference ratio (I_L-Trp/I_D-Trp) of 3.22, and it exhibits a detection limit of 0.26 μM for L-Trp. Moreover, this electrochemical sensor can quantitatively measure Trp isomers in complex samples. Importantly, this electrochemical sensor has the characteristics of high stability, good repeatability, easy fabrication, low cost, and efficient discrimination of tryptophan (Trp) isomers.

Keywords: Chirality; Electrochemical sensor; Enantioselective; d-tryptophan; l-tryptophan.