Chiral Oxazoline-Triazole-Benzothiazole Molecular Triads: Photoactive Sensors for Enantioselective Carbohydrate Recognition in Solution

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