Improved biosynthesis of ethyl (S)-4-chloro-3-hydroxybutanoate by adding l-glutamine plus glycine instead of NAD+ in β-cyclodextrin–water system

He, Yiming; Zhang, Dan‐Ping; Tao, Zheng; Lu, Yun; Ding, Yun; Liu, Feng; Zhu, Zhou‐Hao; Rui, Huan; Zheng, Gao‐Wei; Zhang, Xian

doi:10.1016/j.biortech.2015.01.111

Cited by 19 publications

(7 citation statements)

References 18 publications

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“…It is possibe that the addition of amino acid (Lys) in the conversion system was beneficial to the coenzyme regeneration in cells. Zhang and coworkers gave a similar report that adding l ‐glutamine and Gly in the reaction system could increase intracellular NADH content and reductase activity . Moreover, we tested a mixture of individual components (ChAc and Lys) at the same molar ratio as ChAc/Lys, giving a product yield of 78.4%.…”

Section: Resultsmentioning

confidence: 99%

Design and evaluation of novel bio‐based deep eutectic solvents for highly efficient bioproduction of chiral aryl alcohol

Huang

Wang

2020

J of Chemical Tech & Biotech

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BACKGROUND Deep eutectic solvents (DESs) derived from bio‐available materials are promising eco‐friendly solvents in the field of biocatalysis. However, the type of bio‐based DES is still limited and its application in bioprocess has not been well‐explored. We adopted a design strategy via the combination of choline and amino acids to synthesize novel bio‐based DESs, aimed to enhance biocatalytic efficacy by exploiting the developed DESs as co‐solvents. RESULTS Various bio‐based DESs were synthesized, where the two components are both bio‐available (choline and amino acids). Their performances in the bioreduction of 2‐chloro‐1‐(3,4‐difluorophenyl)ethanone (CFPO) were subsequently evaluated with recombinant Escherichia coli cells. The efficient asymmetric production of (S)‐2‐chloro‐1‐(3,4‐difluorophenyl)ethanol ((S)‐CFPL) was successfully achieved in a developed choline acetate/lysine (ChAc/Lys)‐containing medium. ChAc/Lys can strengthen coenzyme regeneration and properly improve cell membrane permeability during bioreduction, which account for high conversion. After optimized reaction parameters were conducted in the ChAc/Lys‐buffer system, 87.0% (S)‐CFPL yield was observed with > 99.9% enantiomeric excess (ee) value at 1 mol L−1 CFPO content. The substrate loading in the established ChAc/Lys‐buffer system was increased by 3.3‐fold compared to aqueous medium. This bioprocess was also proved to be feasible at 500 mL preparative‐scale with a satisfactory conversion. CONCLUSION ChAc/Lys bio‐DES is a promising and biocompatible co‐solvent. Introducing ChAc/Lys to the reaction system is an effective strategy for challenging high substrate loading for bioreduction. Our results give a valuable insight for developing green and benign sustainable bio‐DESs for biotransformation. © 2020 Society of Chemical Industry

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Section: Resultsmentioning

confidence: 99%

Design and evaluation of novel bio‐based deep eutectic solvents for highly efficient bioproduction of chiral aryl alcohol

Huang

Wang

2020

J of Chemical Tech & Biotech

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“…In addition, the approach of exploiting crude C. tropicalis 104 under oxygen-deficient conditions to alter cell energy metabolism for enhancing catalytic efficiency was more convenient and cost-effective compared to the introduction of exogenous cofactor regeneration, direct addition of an exogenous cofactor or other cosubstrate to enhance cofactor regeneration [34,41].…”

Section: Effect Of Limited Oxygen On C Tropicalis 104 In Bioprocessmentioning

confidence: 99%

High-Efficient Production of (S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol via Whole-Cell Catalyst in Deep-Eutectic Solvent-Containing Micro-Aerobic Medium System

Zhu

et al. 2020

Molecules

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The ratio of substrate to catalyst (S/C) is a prime target for the application of asymmetric production of enantiomerically enriched intermediates by whole-cell biocatalyst. In the present study, an attractive increase in S/C was achieved in a natural deep-eutectic solvent (NADES) containing reaction system under microaerobic condition for high production of (S)-1-[3,5-bis(trifluoromethyl)phenyl]ethanol ((S)-3,5-BTPE) with Candida tropicalis 104. In PBS buffer (0.2 M, pH 8.0) at 200 rpm and 30 °C, 79.5 g (Dry Cell Weight, DCW)/L C. tropicalis 104 maintained the same yield of 73.7% for the bioreduction of 3,5-bis(trifluoromethyl)acetophenone (BTAP) under an oxygen-deficient environment compared with oxygen-sufficient conditions, while substrate load increased 4.0-fold (from 50 mM to 200 mM). Furthermore, when choline chloride:trehalose (ChCl:T, 1:1 molar ratio) was introduced into the reaction system for its versatility of increasing cell membrane permeability and declining BTAP cytotoxicity to biocatalyst, the yields were further increased to 86.2% under 200 mM BTAP, or 72.9% at 300 mM BTAP. After the optimization of various reaction parameters involved in the bioreduction, and the amount of biocatalyst and maltose co-substrate remained 79.5 g (DCW)/L and 50 g/L, the S/C for the reduction elevated 6.3 times (3.8 mM/g versus 0.6 mM/g). By altering the respiratory pattern of the whole-cell biocatalyst and exploiting the ChCl:T-containing reaction system, the developed strategy exhibits an attractive potential for enhancing catalytic efficiency of whole-cell-mediated reduction, and provides valuable insight for the development of whole-cell catalysis.

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“…Recently, asymmetric biocatalytic reduction of ethyl 4‐chloro‐3‐oxobutanoate (COBE) to corresponding chiral alcohol CHBE by whole cells has received considerable attention owing to the regeneration of cofactors in situ and higher stereoselectivity under environmentally friendly reaction conditions . Some studies have been reported on the microbial reduction of COBE to ( S )‐CHBE . However, the product yield is not satisfactory at higher concentrations of COBE in aqueous buffer media.…”

Section: Introductionmentioning

confidence: 99%

“…[5][6][7][8] Some studies have been reported on the microbial reduction of COBE to (S)-CHBE. [9][10][11][12] However, the product yield is not satisfactory at higher concentrations of COBE in aqueous buffer media. The productivity of (S)-CHBE was limited due to the toxicity of COBE to the biocatalyst and the relatively poor solubility of substrate.…”

Section: Introductionmentioning

confidence: 99%

New ionic liquid increase the catalytic efficiency of recombinant Escherichia coli cells‐mediated asymmetric reduction

Fan

Zhang

et al. 2018

J of Chemical Tech & Biotech

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Background Ionic liquids (ILs) have advantages in terms of flexible structure and composition for the whole cell mediated biocatalytic reaction. However, the lack of design strategy for ILs has hampered the development of biocatalysis in non‐aqueous medium. In the present study, to establish an efficient reaction system to obtain vital chiral compounds, a novel IL was designed by combining the superior characteristics of quaternary ammonium‐ and dialkyl‐based cationic surfactant IL to enhance the recombinant Escherichia coli cells‐catalyzed bioreduction efficiency. Results [HOEtN1,1,1][BF4] was synthesized and showed excellent characteristics of low toxicity to the biocatalyst, reduced toxicity of substrate to the microbial cells and moderate increase of cell membrane permeability. In the [HOEtN1,1,1][BF4]‐ containing reaction system, some valuable factors involved in the biocatalytic reduction of ethyl 4‐chloro‐3‐oxobutanoate to ethyl (S)‐4‐chloro‐3‐hydroxybutanoate were found to be: 2.5% (w/v) [HOEtN1,1,1][BF4], 20% (v/v) isopropanol, 3 M COBE, pH 7.0, 30 °C, reacted for 16 h. A yield of 96.7% was obtained under the optimum conditions with above 99% enantiomeric excess value, and the proposed bioprocess was also successfully scaled up to a 5 L fermentor with a yield of 90.7%. Conclusion The developed IL [HOEtN1,1,1][BF4] is a promising solvent for enhancing the efficiency of model bioreduction. It was also evaluated for broadening its application to the biosynthesis of (R)‐[3,5‐bis(trifluoromethyl)phenyl] ethanol catalyzed by recombinant Escherichia coli, with remarkable success. © 2018 Society of Chemical Industry

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Improved biosynthesis of ethyl (S)-4-chloro-3-hydroxybutanoate by adding l-glutamine plus glycine instead of NAD+ in β-cyclodextrin–water system

Cited by 19 publications

References 18 publications

Design and evaluation of novel bio‐based deep eutectic solvents for highly efficient bioproduction of chiral aryl alcohol

Design and evaluation of novel bio‐based deep eutectic solvents for highly efficient bioproduction of chiral aryl alcohol

High-Efficient Production of (S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol via Whole-Cell Catalyst in Deep-Eutectic Solvent-Containing Micro-Aerobic Medium System

New ionic liquid increase the catalytic efficiency of recombinant Escherichia coli cells‐mediated asymmetric reduction

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