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

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Abstract

In this study, lyophilized Pseudomonas aeruginosa based whole-cell biocatalyst was used in the highly efficient and regioselective acylation of helicid with fatty acid vinyl esters in organic solvents. P. aeruginosa whole-cell catalyst showed high biomass and biocatalytic performance using 0.1% (w/v) soybean oil and 0.2% (w/v) tryptone as the carbon and nitrogen source, respectively. The biomass (0.72 g/L) cultivated for 36 h under the optimized conditions was 2-folds higher than that obtained by the use of the initial conditions (0.36 g/L). In addition, the optimized medium was found to be suitable for P. aeruginosa cultured in 3.5-L scale fermentation with high biomass (0.71 g/L) obtained at 24 h. Besides, a high substrate conversion efficiency (ranged from 92 to 99%) and excellent regioselectivity (99%) was achieved when P. aeruginosa whole-cell biocatalyst was applied to synthesize an array of 6′-esters of helicid. The reaction rate varies with varying acyl donors because of their differential interactions with the catalytic site of the enzyme from the whole cells of P. aeruginosa. Taken together, P. aeruginosa whole-cell catalyst obtained using optimal culture medium manifest a promising and highly-regioselective alternative to purified enzymes for the regioselective formation of 6′-esters derivatives of helicid in non-aqueous solvents.

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Fig. 1

source on the biomass and catalytic activity of the whole cells. Culture conditions (w/v): different concentrations of soybean oil, 0.1% tryptone, 0.02% MgSO4·7H2O, 0.5% (NH4)2SO4, 30 °C, 180 rmp and 48 h. Reaction conditions: 0.02 mmol helicid, 0.6 mmol vinyl caprylate, 0.08 g catalyst preparation, 2 mL anhydrous acetone, 40 °C, 200 rpm, 36 h

Fig. 2

source on the biomass and catalytic activity of the whole cells. Culture conditions (w/v): 0.1% soybean oil, different concentrations of tryptone, 0.02% MgSO4·7H2O, 0.5% (NH4)2SO4, 30 °C, 180 rmp and 48 h. Reaction conditions: 0.02 mmol helicid, 0.6 mmol vinyl caprylate, 0.08 g catalyst preparation, 2 mL anhydrous solvent, 40 °C, 200 rpm, 36 h

Fig. 3

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Funding

The authors thank the financial support from the National Natural Science Foundation of China (21706088, 21808075, and 21676114), the Natural Science Foundation of Jiangsu Province (BK20170458 and BK20170459) and the Six Talent Peaks of Jiangsu Province (2018-SWYY-020).

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Author notes

  1. Ting-Ting Wu and Xiang-Jie Zhao have contributed equally to this paper and should be considered as co-first authors.

Authors and Affiliations

  1. School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai’an, 223003, China

    Ting-Ting Wu, Xiang-Jie Zhao, Rong-Ling Yang, Muhammad Bilal, Zhao-Yu Wang, Hong-Zhen Luo, Ning-Ning Xu & Ze-Kun Nie

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  1. Ting-Ting Wu
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  2. Xiang-Jie Zhao
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  4. Muhammad Bilal
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Correspondence to Rong-Ling Yang.

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Wu, TT., Zhao, XJ., Yang, RL. et al. Catalytic Performance of a Robust Whole-Cell Biocatalyst in the Regioselective Synthesis of Helicid Esters Under Optimized Processing Conditions. Catal Lett 150, 1841–1848 (2020). https://doi.org/10.1007/s10562-020-03117-y

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