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Cordyceps fungus-mediated enantioselective synthesis of chiral alcohol and enhanced biocatalytic efficiency in cyclodextrin/surfactant-buffer system

文献类型： 外文期刊

作者： Gui, Qian 1 ; Zhang, Hai -Min 1 ; Qian, Feng 1 ; Liu, Han -Yu 1 ; Kong, Xiang-Xin 1 ; Lv, Guo-Ying 3 ; Wang, Pu 1 ;

作者机构： 1.Zhejiang Univ Technol, Key Lab Green Pharmaceut Technol & Related Equipme, Minist Educ, Hangzhou 310014, Peoples R China

2.Zhejiang Univ Technol, Coll Pharmaceut Sci, Key Lab Pharmaceut Engn Zhejiang Prov, Hangzhou 310014, Peoples R China

3.Zhejiang Acad Agr Sci, Inst Hort, Hangzhou 310021, Peoples R China

关键词： Biocatalysis; Cordyceps spp; Chiral alcohol; Cyclodextrin; Synergistic effect

期刊名称：BIOCHEMICAL ENGINEERING JOURNAL （ 影响因子：3.9； 五年影响因子：4.0 ）

ISSN： 1369-703X

年卷期： 2024 年 205 卷

页码：

收录情况： SCI

摘要： Asymmetric synthesis of chiral alcohols by biocatalysts holds promising prospect. In this study, a medicinal Cordyceps fungus, namely Tolypocladium inflatum, was adopted as a novel biocatalyst for the synthesis of chiral alcohols. Among the assessed prochiral ketone substrates, T. inflatum exhibited the best catalytic activity towards 1-(4-bromophenyl)-2,2,2-trifluoroethanone (BPFO), yielding a valuable pharmaceutical intermediate (S)-1-(4-bromophenyl)-2,2,2-trifluoroethanol ((S)-BPFL) with >99.9 % enantiomeric excesses (ee). For more efficient biosynthesis of (S)-BPFL, cyclodextrins or surfactants were introduced to the reaction system as additives to strengthen this bioprocess. Among which methyl beta-cyclodextrin (MCD) improved cell membrane permeability and alleviated product inhibition, while Triton X-100 enhanced BPFO solubility. Furthermore, synergistic promotion for BPFO bioreduction by MCD and Triton X-100 was observed. Under the optimal reaction conditions, 50 mM BPFO was converted into (S)-BPFL with 89.1 % yield and >99.9 % ee in 12 h, showing 16-fold increase of space-time yield in the developed MCD/Triton X-100-buffer system compared to neat buffer solution. This study illustrated the potential of the enantioselective preparation of chiral alcohols mediated by Cordyceps fungus. Additionally, the biocatalytic efficiency was significantly improved in the constructed synergistic reaction system, and the underlying mechanism was also explored.

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