Enzymatic resolution of epichlorohydrin catalyzed by whole cells in an organic solvent/buffer biphasic system

Zou, Shu-Ping; Yan, Haiwei; Hu, Zhong-Ce; Zheng, Yu‐Guo

doi:10.1016/s1872-2067(12)60576-2

Cited by 16 publications

(7 citation statements)

References 25 publications

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“…However, when the rac ‐ m ‐NSO concentration was elevated to 20 mmol l −1 , its c value was only 70·2% even though the hydrolytic time was prolonged to 20 h, suggesting that there is inhibitory effect of rac ‐ m ‐NSO at high concentration on Pv EH2. This phenomenon was also observed in the enantioconvergent hydrolysis and kinetic resolution of rac ‐epoxides by some other EHs, such as Ar EH and Au EH2 (Zou et al ; Hu et al ).…”

Section: Resultsmentioning

confidence: 65%

Enantioconvergent hydrolysis of m ‐nitrostyrene oxide at an elevated concentration by Phaseolus vulgaris epoxide hydrolase in the organic/aqueous two‐phase system

Wen

Zhao

Liu

et al. 2020

Lett Appl Microbiol

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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-pve-h2. 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. Abstract(R)-m-Nitrophenyl-1,2-ethanediol (m-NPED) is a versatile and highly valueadded 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 Na 2 HPO 4 ÀNaH 2 PO 4 buffer (50 mmol l À1 , pH 7Á0) system, merely 15 mmol l À1 rac-m-NSO was successfully subjected to enantioconvergent hydrolysis, producing (R)-m-NPED with 86Á0% enantiomeric excess (ee p ) and 177Á6 mg l À1 h À1 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 racm-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 (v o /v b ) of petroleum ether to phosphate buffer and the weight ratio (w c /w s ) 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 À1 (6Á6 mg ml À1 ) was carried out at 25°C for 12 h using 33Á0 mg ml À1 vacuum freeze-dried cells of E. coli/pCold-pveh2, producing (R)-m-NPED with 87Á4% ee p , 82Á3% yield and 502Á4 mg l À1 h À1 STY.

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Section: Resultsmentioning

confidence: 65%

Enantioconvergent hydrolysis of m ‐nitrostyrene oxide at an elevated concentration by Phaseolus vulgaris epoxide hydrolase in the organic/aqueous two‐phase system

Wen

Zhao

Liu

et al. 2020

Lett Appl Microbiol

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“…Reaction temperature is a key factor in wholecell conversion as it can influence the activity of critical enzymes such as LDH. In a biphasic system, temperature is also a principal parameter as it influences the stability of the solvent phase as well as the reaction equilibrium (Zou et al, 2013;Resasco, 2014). In this study, we varied the temperature of the conversion system in the range of 30-45 °C and found that the concentration of PLA and the conversion ratio increased with temperature (Fig.…”

Section: Effect Of Reaction Temperature On Pla Synthesismentioning

confidence: 79%

“…PPA concentration is a significant factor that affects the production of PLA. Low PPA concentration will affect PLA production, but high concentration is toxic to cells (Zou et al, 2013). Therefore, we investigated the effect of substrate concentration on the production of PLA in an aqueous phase system and an aqueous/n-octane biphasic system (Fig.…”

Section: Effect Of Substrate Concentration On Pla Synthesismentioning

confidence: 99%

“…So far, there has been no report on any suitable biphasic system to be applied to the biosynthesis of PLA using recombinant E. coli. Some studies have shown that the yield of the target product can be improved by increasing enzymatic activity (Kobayashi et al, 2000;Ni et al, 2013;Delbecq et al, 2016), increasing the solubility of the substrate (Zou et al, 2013;Resasco, 2014), and reducing the inhibitory effects of the substrate and products (Li et al, 2007;Wang et al, 2015) in an aqueous/organic solvent biphasic system. Li et al (2007) reported successful increase in the concentration and e.e.…”

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confidence: 99%

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Biosynthesis of (R)-2-hydroxy-3-phenylpropionic acid using whole recombinant Escherichia coli cells in an aqueous/n-octane biphasic system

Zhu

Yan

Wang

et al. 2018

J. Zhejiang Univ. Sci. B

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(R)-2-hydroxy-3-phenylpropionic acid (PLA) is an ideal antimicrobial compound with broad-spectrum activity against a wide range of Gram-positive bacteria, some Gram-negative bacteria, and fungi. We studied the bioconversion of phenylpyruvate (PPA) to PLA using whole recombinant Escherichia coli cells in a series of buffer/organic solvent systems. Octane was found to be the best organic solvent. The optimum volume ratio of the water phase to the n-octane phase, conversion temperature, substrate concentration, and cell concentration were 6:4, 40 °C, 12.5 g/L, and 30 g/L wet cells, respectively. Under the optimized conditions, the average PLA productivity in the aqueous/ n-octane system was 30.69% higher than that in the aqueous system, and 32.31 g/L PLA was obtained with the use of a stirred reactor (2-L scale). Taken together, our findings indicated that PLA biosynthesis was more efficient in an aqueous/n-octane biphasic system than in a monophasic aqueous system. The proposed biphasic system is an effective strategy for enhancing PLA yield and the biosynthesis of its analogues.

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“…Compared with the chemical method, biotransformation is mild, high conversion and outstanding stereoselectivity [8]. However, the solubility of oxcarbazepine or S-licarbazepine in water is so low that production efficiency is not high in biotransformation [9]. In order to improve the production capacity of biotransformation, interface-assembled carbonyl reductase was used in the reduction of oxcarbazepine to prepare S-licarbazepine in this paper.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Interface-Assembled Carbonyl Reductase and Its Application in Synthesis of S-Licarbazepine in Toluene/Tri-HCl Buffer Biphasic System

Ou¹,

Xu²,

Niu³

et al. 2017

Preprint

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S-licarbazepine was prepared by asymmetric reduction of oxcarbazepine with interface-assembled carbonyl reductase at the interface of oil/water biphasic system. The carbonyl reductase was conjugated with polystyrene in the surface of toluene/Tris-HCl biphasic system and formed a surfactant-like structure. The conversion and enantiometric excess of S-licarbazepine reached 97.39% and 99.6% when 3.97 mmol/L oxcarbazepine was reduced by interface-assembled carbonyl reductase with 60 g/L ethanol as co-substrate in toluene/Tris-HCl(12.5:10) biphasic system at 30 °C, 180 rpm for 6 h.

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Enzymatic resolution of epichlorohydrin catalyzed by whole cells in an organic solvent/buffer biphasic system

Cited by 16 publications

References 25 publications

Enantioconvergent hydrolysis of m ‐nitrostyrene oxide at an elevated concentration by Phaseolus vulgaris epoxide hydrolase in the organic/aqueous two‐phase system

Enantioconvergent hydrolysis of m ‐nitrostyrene oxide at an elevated concentration by Phaseolus vulgaris epoxide hydrolase in the organic/aqueous two‐phase system

Biosynthesis of (R)-2-hydroxy-3-phenylpropionic acid using whole recombinant Escherichia coli cells in an aqueous/n-octane biphasic system

Preparation of Interface-Assembled Carbonyl Reductase and Its Application in Synthesis of S-Licarbazepine in Toluene/Tri-HCl Buffer Biphasic System

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