Catalytic Performance of a Robust Whole-Cell Biocatalyst in the Regioselective Synthesis of Helicid Esters Under Optimized Processing Conditions

Wu, Ting; Zhao, Xiangjie; Yang, Rongling; Bilal, Muhammad; Wang, Zhao-Yu; Luo, Hongzhen; Xu, Ningning; Nie, Zekun

doi:10.1007/s10562-020-03117-y

Cited by 4 publications

(3 citation statements)

References 28 publications

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“…In most cases of HMF bio-oxidation, a complex nutrient-rich medium was an indispensable prerequisite for strain cultivation. , In this study, the abundant and readily available red seaweed was tested as a cheap substrate to cultivate P. rhodesiae NL2019.…”

Section: Resultsmentioning

confidence: 99%

Effective Comprehensive Utilization Strategy for Upgrading Red Seaweed via Chemocatalysis and a Newly Isolated Pseudomonas rhodesiae in Tandem

Liu

Jin

et al. 2023

ACS Sustainable Chem. Eng.

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Red seaweed is a kind of important renewable biomass owing to its great advantages over terrestrial biomass, but present research mainly focused on the biorefinery of fermentable sugars from red seaweeds only. In this study, we proposed an effective comprehensive utilization strategy for upgrading red seaweed (Gelidium amansii) to D-galactose and 5-hydroxymethyl-2furancarboxylic acid (HMFCA) via chemocatalysis and biocatalysis in tandem. With G. amansii as raw feedstock, high yields of Dgalactose (85.5%) and 5-hydroxymethylfurfural (HMF) (50.9%) were first achieved by oxalic acid catalysis. HMF was separated and further selectively oxidized to HMFCA by whole cells of Pseudomonas rhodesiae NL2019 with a yield of 83.9%. Particularly, G. amansii hydrolysate was also used as the carbon source (Dgalactose) for cell growth and as an inducer (HMF) to promote the catalytic capacity of P. rhodesiae cells. In this way, we established a cost-competitive, highly efficient, and environmentally friendly chemoenzymatic approach for the simultaneous valorization of all components of red seaweed.

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Section: Resultsmentioning

confidence: 99%

Effective Comprehensive Utilization Strategy for Upgrading Red Seaweed via Chemocatalysis and a Newly Isolated Pseudomonas rhodesiae in Tandem

Liu

Jin

et al. 2023

ACS Sustainable Chem. Eng.

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“…In the range of 20 to 40 °C, the yield increased with the temperature elevating from 20 to 30 °C, and then decreased at the temperature above 30 °C. During the asymmetric biological reduction, the biocatalyst dosage is a significant issue, which can affect the efficiency of biocatalytic reaction (Wu et al 2020 ). As shown in Fig.…”

Section: Resultsmentioning

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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“…For more efficient production by biocatalytic process, there are many process metrics to control, such as substrate conversion efficiency, catalyst recycling or ratio of substrate to catalyst (S/C) [17][18][19]. For example, a high S/C ratio is one of significant issues in highly efficient preparation via biocatalysis.…”

Section: Introductionmentioning

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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Catalytic Performance of a Robust Whole-Cell Biocatalyst in the Regioselective Synthesis of Helicid Esters Under Optimized Processing Conditions

Cited by 4 publications

References 28 publications

Effective Comprehensive Utilization Strategy for Upgrading Red Seaweed via Chemocatalysis and a Newly Isolated Pseudomonas rhodesiae in Tandem

Effective Comprehensive Utilization Strategy for Upgrading Red Seaweed via Chemocatalysis and a Newly Isolated Pseudomonas rhodesiae in Tandem

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

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

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