Abstract
BackgroundDeep eutectic solvents have attracted considerable attention in numerous fields. There is little information on mung bean epoxide hydrolase-catalyzed epoxides in deep eutectic solvent-containing system.ResultsAdding deep eutectic solvents with hydrogen bond donor of acids to phosphate buffer resulted in an obvious decrease in the optical purity of product; nevertheless, the relative slight change was observed by the addition of the deep eutectic solvents with hydrogen bond donor of alcohols and urea. Of the tested deep eutectic solvents, 10% additional amount of choline chloride/trithylene glycol can cause a significant improvement in the enantiopurity of product, from 83.2 ± 1.3% to 87.9 ± 0.3%. Moreover, with the increase in the addition amount of choline chloride/triethylene glycol from 10 to 30%, the enantiomeric excess of product enhanced from 87.9 to 94%, but a decline of product yield was observed. Finally, the evaluation of enzyme stability showed that the additional amount from 10% to 30% was not beneficial to the activity recovery.ConclusionIn short, adding choline chloride/triethylene glycol contributes to the improvement in the optical purity of (R)-1-phenyl-1, 2-ethanediol in the catalysis of styrene oxide by mung bean epoxide hydrolases; meanwhile, the enzyme immobilization could be essential.
Highlights
Deep eutectic solvents have attracted considerable attention in numerous fields
Compared to an aqueous monophasic system, a biphasic reaction system composed of n-hexane and phosphate buffer controlled the non-enzymatic hydrolysis of styrene oxide (SO) achieving better optical purity of the product, and increased the maximum reaction concentration of the substrate from 5 to 20 mM (Chen et al 2011, 2012b)
We studied the effect of ChCl/ TEG concentrations on the yield and enantiopurity of (R)-PED by the asymmetric hydrolysis of SO because of a slightly better optical purity of the product achieved
Summary
There is little informa‐ tion on mung bean epoxide hydrolase-catalyzed epoxides in deep eutectic solvent-containing system. There is no doubt that chiral pure epoxides and vicinal diols have an important role in the synthesis of pharmaceuticals, pesticides and cosmetics (Hwang et al 2008; Kotik et al 2005; Xu et al 2006). Among them, (S)-glycidyl phenyl ether is an important raw material for the synthesis of β-adrenergic receptor blockers by selective nucleophilic addition of amines to a single epoxide enantiomer (Gong and Xu 2005). At the same time, adding a small amount of hydrophilic ionic liquid as co-solvent can increase the stability of the mung bean epoxide hydrolases (mEHs) and the solubility of the reaction substrate in the buffer (Chen et al 2011, 2012b). To overcome the drawbacks of organic solvents, deep eutectic solvents (DESs) as new green solvents have emerged at early this century
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