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

Abstract

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.

Keywords

Deep eutectic solvents / Epoxide hydrolase / Styrene oxide / 1-Phenyl-1,2-ethanediol

References

[1] Bala N, Chimni SS, Saini HS, Chadha BS. Bacillus alcalophilus MTCC10234 catalyzed enantioselective kinetic resolution of aryl glycidyl ethers. J Mol Catal B Enzym, 2010, 63: 128-134.

[2] Cao SL, Yue DM, Li XH, Smith TJ, Li N, Zong MH, Lou WY. Novel nano-/micro-biocatalyst: soybean epoxide hydrolase immobilized on UiO-66-NH2 MOF for efficient biosynthesis of enantiopure (R)-1,2-octanediol in deep eutectic solvents. ACS Sustain Chem Eng, 2016, 4: 3586-3595.

[3] Chen WJ, Lou WY, Wang X, Zong MH. Asymmetric hydrolysis of styrene oxide catalyzed by mung bean epoxide hydrolase in organic solvent/buffer biphasic system. Chin J Catal, 2011, 32: 1557-1563.

[4] Chen WJ, Lou WY, Zong MH. Efficient asymmetric hydrolysis of styrene oxide catalyzed by mung bean epoxide hydrolases in ionic liquid-based biphasic systems. Bioresour Technol, 2012, 115: 58-62.

[5] Chen WJ, Lou WY, Yu CY, Wu H, Zong MH, Smith TJ. Use of hydrophilic ionic liquids in a two-phase system to improve mung bean epoxide hydrolases-mediated asymmetric hydrolysis of styrene oxide. J Biotechnol, 2012, 162: 183-190.

[6] Flores-Ferrándiz J, Chinchilla R. Organocatalytic enantioselective conjugate addition of aldehydes to maleimides in deep eutectic solvents. Tetrahedron Asymmetry, 2017, 28: 302-306.

[7] Gong PF, Xu JH. Bio-resolution of a chiral epoxide using whole cells of Bacillus megaterium ECU1001 in a biphasic system. Enzym Microb Technol, 2005, 36: 252-257.

[8] Gore S, Baskaran S, Koenig B. Efficient synthesis of 3, 4-dihydropyrimidin-2-ones in low melting tartaric acid–urea mixtures. Green Chem, 2011, 13: 1009-1013.

[9] Gorke JT, Srienc F, Kazlauskas RJ. Hydrolase-catalyzed biotransformations in deep eutectic solvents. Chem Commun, 2008, 10: 1235-1237.

[10] Guajardo N, Domínguez de María P, Ahumada K, Schrebler RA, Ramírez-Tagle R, Crespo FA, Carlesi C. Water as cosolvent: nonviscous deep eutectic solvents for efficient lipase-catalyzed esterifications. ChemCatChem, 2017, 9(8): 1393-1396.

[11] Harifi-Mood AR, Ghobadi R, Divsalar A. The effect of deep eutectic solvents on catalytic function and structure of bovine liver catalase. Int J Biol Macromol, 2017, 95: 115-120.

[12] Hwang S, Choi CY, Lee EY. Enantioconvergent bioconversion of p-chlorostyrene oxide to (R)-p-chlorophenyl-1,2-ethandiol by the bacterial epoxide hydrolase of Caulobacter crescentus. Biotechnol Lett, 2008, 30: 1219-1225.

[13] Juneidi I, Hayyan M, Hashim MA, Hayyan A. Pure and aqueous deep eutectic solvents for a lipase-catalysed hydrolysis reaction. Biochem Eng J, 2017, 117: 129-138.

[14] Kamble MP, Yadav GD. Biocatalytic resolution of (R, S)-styrene oxide using a novel epoxide hydrolase from red mung beans. Catal Today, 2017

[15] Kotik M, Brichac J, Kyslík P. Novel microbial epoxide hydrolases for biohydrolysis of glycidyl derivatives. J Biotechnol, 2005, 120: 364-375.

[16] Lindberg D, de la Fuente Revenga M, Widersten M. Deep eutectic solvents (DESs) are viable cosolvents for enzyme-catalyzed epoxide hydrolysis. J Biotechnol, 2010, 147: 169-171.

[17] Lobo HR, Singh BS, Shankarling GS. Deep eutectic solvents and glycerol: a simple, environmentally benign and efficient catalyst/reaction media for synthesis of N-aryl phthalimide derivatives. Green Chem Lett Rev, 2012, 5(4): 487-533.

[18] Lobo HR, Singh BS, Shankarling GS. Lipase and deep eutectic mixture catalyzed efficient synthesis of thiazoles in water at room temperature. Catal Lett, 2012, 142(11): 1369-1375.

[19] Lu W, Alam MA, Pan Y, Wu J, Wang Z, Yuan Z. A new approach of microalgal biomass pretreatment using deep eutectic solvents for enhanced lipid recovery for biodiesel production. Bioresour Technol, 2016, 218: 123-128.

[20] Nie Y, Xu Y, Mu XQ. Highly enantioselective conversion of racemic 1-phenyl-1,2-ethanediol by stereoinversion involving a novel cofactor-dependent oxidoreduction system of Candida parapsilosis CCTCC M203011. Org Process Res Dev, 2004, 8: 246-251.

[21] Radošević K, Ćurko N, Srček VG, Bubalo MC, Tomašević M, Ganić KK, Redovniković IR. Natural deep eutectic solvents as beneficial extractants for enhancement of plant extracts bioactivity. LWT Food Sci Technol, 2016, 73: 45-51.

[22] Simeó Y, Faber K. Selectivity enhancement of enantio- and stereo-complementary epoxide hydrolases and chemo-enzymatic deracemization of (±)-2-methylglycidyl benzyl ether. Tetrahedron Asymmetry, 2006, 17: 402-409.

[23] Wu BP, Wen Q, Xu H, Yang Z. Insights into the impact of deep eutectic solvents on horseradish peroxidase: activity, stability and structure. J Mol Catal B Enzym, 2014, 101: 101-107.

[24] Xu W, Xu JH, Pan J, Gu Q, Wu XY. Enantioconvergent hydrolysis of styrene epoxides by newly discovered epoxide hydrolases in mung bean. Org Lett, 2006, 8: 1737-1740.

[25] Xu P, Cheng J, Lou WY, Zong MH. Using deep eutectic solvents to improve the resolution of racemic 1-(4-methoxyphenyl) ethanol through Acetobacter sp. CCTCC M209061 cell-mediated asymmetric oxidation. RSC Adv, 2015, 5: 6357-6364.

[26] Xu P, Xu Y, Li XF, Zhao BY, Zong MH, Lou WY. Enhancing asymmetric reduction of 3-chloropropiophenone with immobilized Acetobacter sp. CCTCC M209061 cells by using deep eutectic solvents as cosolvents. ACS Sustain Chem Eng, 2015, 3: 718-724.

[27] Yang SL, Duan ZQ. Insight into enzymatic synthesis of phosphatidylserine in deep eutectic solvents. Catal Commun, 2016, 82: 16-19.

[28] Yu CY, Li XF, Lou WY, Zong MH. Cross-linked enzyme aggregates of mung bean epoxide hydrolases: a highly active, stable and recyclable biocatalyst for asymmetric hydrolysis of epoxides. J Biotechnol, 2013, 166: 12-19.

[29] Zhang Q, Vigier KDO, Royer S, Jérôme F. Deep eutectic solvents: syntheses, properties and applications. Chem Soc Rev, 2012, 41: 7108-7146.

[30] Zhao H, Baker GA, Holmes S. Protease activation in glycerol-based deep eutectic solvents. J Mol Catal B Enzym, 2011, 72: 163-167.

[31] Zhao BY, Xu P, Yang FX, Wu H, Zong MH, Lou WY. Biocompatible deep eutectic solvents based on choline chloride: characterization and application to the extraction of rutin from Sophora japonica. ACS Sustain Chem Eng, 2015, 3: 2746-2755.

Funding

National Natural Science Foundation of China(21676104)

the Program of State Key Laboratory of Pulp and Paper Engineering(2017ZD05)

the Open Funding Project of the State Key Laboratory of Bioreactor Engineering