Wen_2020_Lett.Appl.Microbiol_70_181

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Title : Enantioconvergent hydrolysis of m-nitrostyrene oxide at an elevated concentration by Phaseolus vulgaris epoxide hydrolase in the organic\/aqueous two-phase system - Wen_2020_Lett.Appl.Microbiol_70_181
Author(s) : Wen Z , Zhao J , Liu YY , Zhou JJ , Liu C , Li C , Wu MC
Ref : Lett Appl Microbiol , 70 :181 , 2020
Abstract : (R)-m-Nitrophenyl-1,2-ethanediol (m-NPED) is a versatile and highly value-added chiral building block for the synthesis of some bioactive compounds, such as (R)-Nifenalol. To efficiently produce (R)-m-NPED through the enantioconvergent hydrolysis of racemic (rac-) m-nitrostyrene oxide (m-NSO) using the whole resting cells of Escherichia coli/pCold-pveh2 intracellularly expressing PvEH2, an epoxide hydrolase from Phaseolus vulgaris, two reaction systems were investigated. In the Na2 HPO4 -NaH2 PO4 buffer (50 mmol l(-1) , pH 7.0) system, merely 15 mmol l(-1) rac-m-NSO was successfully subjected to enantioconvergent hydrolysis, producing (R)-m-NPED with 86.0% enantiomeric excess (eep ) and 177.6 mg l(-1) h(-1) space-time yield (STY). The experimental result indicated that there is inhibitory effect of rac-m-NSO at high concentration on PvEH2. To efficiently increase the concentration of rac-m-NSO and the STY of (R)-m-NPED, petroleum ether was first selected to construct an organic/aqueous two-phase system. Then, both the volume ratio (vo /vb ) of petroleum ether to phosphate buffer and the weight ratio (wc /ws ) of E. coli/pCold-pveh2 dry cells to rac-m-NSO were optimized as 2 : 8 and 5 : 1, respectively. In the optimized petroleum ether/phosphate buffer two-phase system, the enantioconvergent hydrolysis of rac-m-NSO at 40 mmol l(-1) (6.6 mg ml(-1) ) was carried out at 25 degrees C for 12 h using 33.0 mg ml(-1) vacuum freeze-dried cells of E. coli/pCold-pveh2, producing (R)-m-NPED with 87.4% eep , 82.3% yield and 502.4 mg l(-1) h(-1) STY. SIGNIFICANCE AND IMPACT OF THE STUDY: Epoxide hydrolases play a crucial role in producing enantiopure epoxides and/or vicinal diols. However, numerous biocatalytic reactions of organic compounds, such as epoxides, in aqueous phase suffered various restrictions. Herein, the enantioconvergent hydrolysis of rac-m-NSO in two reaction systems was investigated using the whole cells of Escherichia coli/pCold-pveh2. As a result, the concentration of rac-m-NSO and the space-time yield of (R)-m-NPED in organic/aqueous two-phase system were significantly increased, when compared with those in aqueous phase. To our knowledge, this is the first report about the production of (R)-m-NPED from rac-m-NSO at an elevated concentration by PvEH2 in the two-phase system.
ESTHER : Wen_2020_Lett.Appl.Microbiol_70_181
PubMedSearch : Wen_2020_Lett.Appl.Microbiol_70_181
PubMedID: 31784998

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Wen Z, Zhao J, Liu YY, Zhou JJ, Liu C, Li C, Wu MC (2020)
Enantioconvergent hydrolysis of m-nitrostyrene oxide at an elevated concentration by Phaseolus vulgaris epoxide hydrolase in the organic\/aqueous two-phase system
Lett Appl Microbiol 70 :181

Wen Z, Zhao J, Liu YY, Zhou JJ, Liu C, Li C, Wu MC (2020)
Lett Appl Microbiol 70 :181