Efficient biosynthesis of (S)-1-[2-(trifluoromethyl)phenyl]ethanol by a novel isolate Geotrichum silvicola ZJPH1811 in deep eutectic solvent/cyclodextrin-containing system

Xiong, Lilu; Kong, Xiangxin; Liu, Hanyu; Wang, Pu

doi:10.1016/j.biortech.2021.124832

Cited by 11 publications

(11 citation statements)

References 40 publications

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“…However, comparing the two series, ChCl-based DESs were found to be more deleterious than ChOAc-based ones, giving hence a boost to the design and application of OAc-based DESs. Unlike the parent ChCl-based DESs, a few mixtures of ChOAc and a HBD have been characterized, , and suggested as media for organic synthesis, enzymatic reactions, − or biomass treatment …”

Section: Introductionmentioning

confidence: 99%

In Competition for Water: Hydrated Choline Chloride:Urea vs Choline Acetate:Urea Deep Eutectic Solvents

Pietro

Tortora

Bottari

et al. 2021

ACS Sustainable Chem. Eng.

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Unlike the archetypal deep eutectic solvent (DES) choline chloride:urea (ChCl:U), fundamental knowledge of the intermolecular network in choline acetate (ChOAc) DESs and how they change upon dilution is still missing. Here we jointly use UV resonance Raman (UVRR) and NMR spectroscopy to comparatively explore how the strength and distribution of hydrogen bonding and the solvation of the components are modified in ChOAc:U and ChCl:U with increasing hydration. Overall, Raman and NMR data indicate that ChOAc:U is continuously affected by hydration and, even at low water concentrations, undergoes a breakage of DES–DES interactions, with rapid solvation of the urea portion and full exchange of mobile protons. On the contrary, ChCl:U seems to maintain its structure as small interplays gradually occur between urea in the DES and the surrounding water molecules. The combined approach provides a multifaceted consistent description of the systems, outlining the crucial role of the anion in driving the structure and dynamics of the materials and then yielding valuable data toward the exploitation of DESs as tunable systems.

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Section: Introductionmentioning

confidence: 99%

In Competition for Water: Hydrated Choline Chloride:Urea vs Choline Acetate:Urea Deep Eutectic Solvents

Pietro

Tortora

Bottari

et al. 2021

ACS Sustainable Chem. Eng.

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“…2 e), the increase of substrate concentration significantly reduced the conversion efficiency, so an increasing conversion efficiency was desirable. It has been reported that the introduction of DES as cosolvent can improve the substrate loading and obtain higher biocatalysis efficiency by improving the permeability of cellular membrane in the biotransformation (Xiong et al 2021 ; He et al 2020 ). Surfactants, as a kind of cosolvent to improve the solubility of hydrophobic compounds, are helpful in the biocatalysis process (Benvenutti et al 2019 ; Patzold et al 2019 ).…”

Section: Discussionmentioning

confidence: 99%

Effective asymmetric preparation of (R)-1-[3-(trifluoromethyl)phenyl]ethanol with recombinant E. coli whole cells in an aqueous Tween-20/natural deep eutectic solvent solution

et al. 2021

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Abstract(R)-1-[3-(Trifluoromethyl)phenyl]ethanol ((R)-MTF-PEL) is an important chiral building block for the synthesis of a neuroprotective compound, (R)-3-(1-(3-(trifluoromethyl)phenyl)ethoxy)azetidine-1-carboxamide. In this work, an effective whole-cell-catalyzed biotransformation was developed to produce (R)-MTF-PEL, and its productivity was increased by medium engineering strategy. The recombinant E. coli BL21(DE3)-pET28a(+)-LXCAR-S154Y variant affording carbonyl reductase was adopted for the reduction of 3'-(trifluoromethyl)acetophenone to (R)-MTF-PEL with enantiomeric excess (ee) > 99.9%. The addition of 0.6% Tween-20 (w/v) boosted the bioreduction, because the substrate concentration was increased by 4.0-fold than that in the neat buffer solution. The biocatalytic efficiency was further enhanced by introducing choline chloride: lysine (ChCl:Lys, molar ratio of 1:1) in the reaction medium, because the product yield reached 91.5% under 200 mM substrate concentration in the established Tween-20/ChCl:Lys-containing system, which is the highest ever reported for (R)-MTF-PEL production. The optimal reduction conditions were as follows: 4% (w/v) ChCl:Lys, 12.6 g (DCW)/L recombinant E. coli cells, pH 7.0, 30 ℃ and 200 rpm, reaction for 18 h. The combined strategy of surfactant and NADES has great potential in the biocatalytic process and the synthesis of chiral alcohols.

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“…Asymmetric biocatalytic reactions have evolved increasingly broad applications in pharmaceutical synthesis [25,26]. Screening biocatalysts with high ee value and yield is quite principal in biocatalysis [7]. After multiple cycles of screening, a fungal strain B-36 exhibited the highest catalytic efficiency, showing excellent enantioselectivity (>99% ee) and yield (~90.7%) to produce (S)-1-chloro-2-heptanol.…”

Section: Isolation and Characterization Of Strain B-36mentioning

confidence: 99%

“…The yield of (S)-1-chloro-2-heptanol was sharply decreased with continuously increased IPA concentration from 25% to 30%. It is demonstrated that the appropriate concentration of IPA can accelerate the asymmetric bioreduction efficiency, and the higher IPA concentration (25-30%) may unbalance the osmotic pressure of the cells and the enzyme rush in the reaction system [7]. The original existing coenzyme regeneration system in whole cells has been destroyed; therefore, the biocatalytic reduction is terminated, resulting in the yield sharply decreasing [29].…”

Section: Isopropanol Concentrationmentioning

confidence: 99%

“…Biosynthesis has been described as a distinguished and simple pathway to synthesize active enantiomerically pharmaceutical intermediates, accessing high stereoselectivity (ee > 99%), 100% of theoretical yield, room reaction temperature, metalfree catalysts, etc. [6,7]. Biocatalysis, as an environmentally benign technology, offers a pollution-free approach to asymmetric synthesis [8,9].…”

Section: Introductionmentioning

confidence: 99%

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Efficient Biosynthesis of (S)-1-chloro-2-heptanol Catalyzed by a Newly Isolated Fungi Curvularia hominis B-36

Lin

Chen

et al. 2022

Catalysts

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(S)-1-chloro-2-heptanol is an enantiopure chemical of great value that can synthesize Treprostinil for treating primary pulmonary hypertension. In this work, a new strain B-36, capable of asymmetric reduction of 1-chloro-2-heptanone to (S)-1-chloro-2-heptanol, was screened and identified as Curvularia hominis B-36 (CCTCC M 2017654) based on the morphological and internally transcribed spacer (ITS) sequence. The reductive capacity of Curvularia hominis B-36 was investigated as a whole-cell biocatalyst in the bioreduction, and the excellent yield (97.2%) and enantiomeric excess (ee) value (99.9%) were achieved under the optimal conditions as follows: 75 mM 1-chloro-2-heptanone, K2HPO4-KH2PO4 (100 mM, pH 6.0), 50 g L−1 resting cells (dry cell weight; DCW), 15% (v/v) isopropanol as co-substrate, 200 rpm, 30 °C, 20 h. The scaled-up biocatalytic process was accomplished at a bioreactor in a 1.5 L working volume, showing superb yield (~97%) and selectivity (99.9%). The product (S)-1-chloro-2-heptanol was purified and characterized by NMR. Curvularia hominis B-36 is a novel catalyst and the asymmetric synthesis route is benign and eco-friendly.

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Efficient biosynthesis of (S)-1-[2-(trifluoromethyl)phenyl]ethanol by a novel isolate Geotrichum silvicola ZJPH1811 in deep eutectic solvent/cyclodextrin-containing system

Cited by 11 publications

References 40 publications

In Competition for Water: Hydrated Choline Chloride:Urea vs Choline Acetate:Urea Deep Eutectic Solvents

In Competition for Water: Hydrated Choline Chloride:Urea vs Choline Acetate:Urea Deep Eutectic Solvents

Effective asymmetric preparation of (R)-1-[3-(trifluoromethyl)phenyl]ethanol with recombinant E. coli whole cells in an aqueous Tween-20/natural deep eutectic solvent solution

Efficient Biosynthesis of (S)-1-chloro-2-heptanol Catalyzed by a Newly Isolated Fungi Curvularia hominis B-36

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