Tetraphenylethylene-based Glycoconjugate as a Fluorescence "Turn-On" Sensor for Cholera Toxin

Tetraphenylethylene (TPE)‐based glycoconjugates were easily synthesized by copper(I)‐catalyzed “click reactions” between propargyl‐attached TPE and azido‐functionalized sugars. The TPE compound bearing lactosyl moieties (Lac‐TPE) was found to be a fluorescence “turn‐on” sensor for cholera toxin by virtue of aggregation‐induced emission characteristics of the TPE motif owing to the specific interaction of lactose with the cholera toxin B subunit, whilst a cellobiose‐functionalized TPE derivative did not show any response to the toxin. Therefore, Lac‐TPE shows promising applications in the detection of cholera toxin, as well as in the investigation of carbohydrate–protein interaction. Tale of the TPE: Tetraphenylethylene‐based glycoconjugates bearing lactosyl moieties can serve as a fluorescence “turn‐on” sensor for cholera toxin by virtue of aggregation‐induced emission characteristics of TPE motif.