Regioselective Synthesis of β-D-Glucopyranosides and Their Analogs by Plant Seed-Derived β-Glycosidases

Regioselective enzymatic glycosylation of D-glucose and various structural alcohols for synthesizing β-D-glucopyranosides was successfully conducted. Among the β-glycosidases from seven potential plant seeds, the low-cost β-glycosidase from Prunus persica seed displayed excellent activity for salidroside preparation. Several crucial parameters, such as the solvent, buffer pH, buffer content, substrate molar ratio, enzyme dosage, and temperature were examined for yield optimization. Under the optimal conditions, the initial reaction rate and yield of salidroside were as high as 3.04 mM/h and 18.90%, respectively. Moreover, the alcohol acceptor recognition of the enzyme in synthesizing β-D-glucopyranosides was also investigated. The experimental data indicated that β-glycosidase activity and yield varied widely among all the tested alcohols due to the specific spatial structures of various acceptors.