Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives

Table 1

Effect of solvent on CALB-catalyzed acylation of polydatin with vinyl sorbate.

Medium		Viscosity	Solubility (mM)	(mM/h)	(%)	6′′-Regioselectivity (%)
2-MeTHF	0.99	0.60	8.51 ± 0.42	3.04 ± 0.15	99.57 ± 0.03	100
t-Amyl alcohol	1.24	3.70	5.87 ± 0.21	2.40 ± 0.11	79.31 ± 0.71	100
t-Butanol	0.60	3.30	6.54 ± 0.26	1.64 ± 0.05	99.00 ± 0.02	100
Cyclohexanone	1.43	2.20	13.96 ± 0.39	0.83 ± 0.06	66.72 ± 1.01	100
Acetone	−0.23	0.32	12.63 ± 0.53	0.62 ± 0.03	99.00 ± 0.02	100
THF	0.49	0.55	72.17 ± 2.98	0.35 ± 0.01	43.22 ± 1.76	100
Dioxane	−1.10	1.30	20.72 ± 1.01	0.21 ± 0.01	25.16 ± 1.31	100

The reactions were carried out at 40°C and 200 rpm by adding 0.03 mmol polydatin, 0.15 mmol vinyl sorbate, and 100 mg CALB into 3 mL anhydrous solvent.
The viscosity of solvents at 25°C.
The solubility of polydatin was determined by HPLC analyses of the saturated solutions at 25°C.