Enzymatic synthesis of tyrosol glycosides

• Three glycosides of tyrosol prepared by enzymatic transglycosidation.
• Salidroside prepared in 6.7% yield.
• Tyrosol β-galactoside prepared for the first time enzymatically in 10.9% yield.
• Tyrosol α-galactoside prepared as a new substance in 32.2% yield.

For the purpose of synthesis of tyrosol β-d-glucopyranoside (salidroside) and its β-d- and α-d-galactopyranoside analogues, transglycosylation of tyrosol with fungal glycosidases (from Aspergillus niger and Aspergillus oryzae) was executed. Cellobiose, lactose and melibiose served as glycosyl donor giving 6.7% yield of salidroside, 10.9% of tyrosol β-d-galactopyranoside, and 32.2% of α-d-galactopyranoside. The glycosylations proceeded on the primary hydroxyl of the tyrosol.

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