Chiral Oxazoline-Triazole-Benzothiazole\nMolecular\nTriads: Photoactive Sensors for Enantioselective Carbohydrate Recognition\nin Solution

Understanding the mechanism of drug action in biological\nsystems\nis facilitated by the interactions between small molecules and target\nchiral biomolecules. In this context, focusing on the enantiomeric\nrecognition of carbohydrates in solution through steady-state fluorescence\nemission spectroscopy is noteworthy. To this end, we have developed\na third generation of chiral optical sensors for carbohydrates, distinct\nfrom all of those previously presented, which interact with carbohydrates\nto form non-covalent probe-analyte interactions. The proposed sensor\nis based on 2-oxazolines bearing a fluorophoric benzothiazole unit.\nWe evaluated their photophysical properties in the presence of enantiomeric\npairs of arabinose, mannose, xylose, and glucose in solution. Our\nprimary findings indicate that the compounds outlined in this study\nwere able to distinguish between enantiomeric pairs in solution, demonstrating\ngood to excellent enantioselectivity through simple intermolecular\ninteractions. To achieve the best enantioselectivity results, theoretical\ncalculations were performed to better understand the observed interactions\nbetween the sensors and the analytes.