Enantioconvergent Hydrolysis of Styrene Epoxides by Newly Discovered Epoxide Hydrolases in Mung Bean

Xu, Wei; Xu, Jian‐He; Pan, Jiang; Gu, Qianqun; Wu, Xin‐Yan

doi:10.1021/ol060407u

Cited by 82 publications

(29 citation statements)

References 37 publications

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“…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). Glycidyl phenyl ether is a vital drug intermediate for the preparing aryloxy propanolamines (Bala et al 2010).…”

Section: Introductionmentioning

confidence: 99%

The effect of deep eutectic solvents on the asymmetric hydrolysis of styrene oxide by mung bean epoxide hydrolases

Peng

Zhao

et al. 2018

Bioresour. Bioprocess.

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Background: Deep 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. Results:Adding 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. Conclusion:In 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.

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Section: Introductionmentioning

confidence: 99%

The effect of deep eutectic solvents on the asymmetric hydrolysis of styrene oxide by mung bean epoxide hydrolases

Peng

Zhao

et al. 2018

Bioresour. Bioprocess.

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“…Samples of the toluene layer were dried over anhydrous sodium sulfate for high-performance liquid chromatography (HPLC) analysis. The conversion (c) and enantiomeric excess (ee) were determined by means of HPLC according to previous reports [14][15][16][17][18][19][20][21].…”

Section: Enantioselective Hydrolysismentioning

confidence: 99%

Significantly Improved Expression and Biochemical Properties of Recombinant Serratia marcescens Lipase as Robust Biocatalyst for Kinetic Resolution of Chiral Ester

Wang

Zhao

et al. 2010

Appl Biochem Biotechnol

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A lipase gene from Serratia marcescens ECU1010 was cloned into expression vector pET28a, sequenced, and overexpressed as an N terminus His-tag fusion protein in Escherichia coli. Through the optimization of culture conditions in shake flask, the lipase activity was improved up to 1.09 x 10⁵ U/l, which is a great improvement compared to our previous reports. It was purified to homogeneity by Ni-NTA affinity chromatography with an overall yield of 59.4% and a purification factor of 2.4-fold. This recombinant lipase displayed excellent stability below 30 °C and within the pH range of 5.0-6.8, giving temperature and pH optima at 40 °C and pH 9.0, respectively. The lipase activity was found to increase in the presence of metal ions such as Ca²+, Cu²+, and some nonionic surfactants such as PEG series. In addition, among p-nitrophenyl esters of fatty acids with varied chain length, the recombinant lipase showed the maximum activity on p-nitrophenyl laurate (C₁₂). Using racemic trans-3-(4'-methoxy-phenyl)-glycidyl methyl ester [(±)-MPGM] as substrate, which is a key chiral synthon for production of diltiazem, a 50% conversion yield was achieved after 4 h in toluene-water (100 mM KPB phosphate buffer, pH 7.5) biphasic system (5:5 ml) at 30 °C under shaking condition (160 rpm), affording (-)-MPGM in nearly 100% ee. The K(m) and V(max) values of the lipase for (±)-MPGM were 222 mM and 1.24 mmol min⁻¹ mg⁻¹, respectively. The above-mentioned features make the highly enantioselective lipase from Serratia marcescens ECU1010 a robust biocatalyst for practical use in large-scale production of diltiazem intermediate.

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“…The recombinant EH hydrolysed both styrene oxide enantiomers but with opposite regioselectivities to give only the R -diol. In the case of mung bean EH's, two enzymes were isolated that displayed opposite enantiopreferences: mbEHA preferentially hydrolysed the S-epoxide by regioselective attack at the a-C (inversion of configuration) to yield the R-diol, while mbEHB preferentially hydrolysed the R-epoxide by regioselective attack at the b-C (retention of configuration) to produce the R-diol from styrene oxide (Xu et al, 2006 ). In contrast, when expressed in Y .…”

Section: Resolution Of Epoxidesmentioning

confidence: 99%

Applications of the Non-Conventional Yeast Yarrowia lipolytica

Nicaud

Gaillardin

2009

Yeast Biotechnology: Diversity and Applications

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Enantioconvergent Hydrolysis of Styrene Epoxides by Newly Discovered Epoxide Hydrolases in Mung Bean

Cited by 82 publications

References 37 publications

The effect of deep eutectic solvents on the asymmetric hydrolysis of styrene oxide by mung bean epoxide hydrolases

The effect of deep eutectic solvents on the asymmetric hydrolysis of styrene oxide by mung bean epoxide hydrolases

Significantly Improved Expression and Biochemical Properties of Recombinant Serratia marcescens Lipase as Robust Biocatalyst for Kinetic Resolution of Chiral Ester

Applications of the Non-Conventional Yeast Yarrowia lipolytica

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