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<p>Alkyloxime and oxime ether derivatives are key intermediates in synthesizing biologically active compounds, pharmaceuticals, and agrochemicals. This study presents an innovative enzymatic approach for synthesizing alkyloximes and alkyloximes (N-OH) derivatives, addressing limitations of conventional methods such as harsh reaction conditions, low yield, and moisture sensitivity. Using <i>Candida antarctica</i> lipase B as a biocatalyst under mild conditions (42&#xa0;°C, 3.5&#xa0;h in dimethyl sulfoxide), methyl benzoylformate was efficiently converted into oximes ether (Z and E isomers with upto 87% and 8% yield respectively) and alkyloximes (Z and E isomer with up to 92% and 0% yield respectively) via reactions with methoxyamine and hydroxylamine, respectively. The enzymatic strategy not only significantly shortens reaction times but also enhances selectivity, favoring the Z isomer over the E isomer due to the enzyme’s active site orientation, which reduces steric hindrance. Furthermore, the method demonstrated improved efficiency compared to traditional chemical synthesis, offering higher yields. Based on the results mechanism was proposed, revealing that the enzyme activates the carbonyl carbon of Compound 1&#xa0;A, to generate an electrophilic carbon, initiating the reaction. Electron donating groups enhance yield by stabilizing the transition state and improving enzyme-substrate interactions. The enzyme catalysis approach is more environmentally sustainable and scalable, aligning with green chemistry principles and offering a promising alternative for the synthesis of bioactive molecules.</p> Graphical Abstract <p></p>

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Biocatalytic syn-stereoselective synthesis of alkyloxime, oxime ether, and their derivatives

  • 期刊论文

  • 发表日期：

    2025年11月21日

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  • Taimur Khan,
  • Khan Bahadar,
  • Maaz Khan,
  • Gao Hanzi,
  • Muhammad Shahab,
  • Guojun Zheng

摘要

Alkyloxime and oxime ether derivatives are key intermediates in synthesizing biologically active compounds, pharmaceuticals, and agrochemicals. This study presents an innovative enzymatic approach for synthesizing alkyloximes and alkyloximes (N-OH) derivatives, addressing limitations of conventional methods such as harsh reaction conditions, low yield, and moisture sensitivity. Using Candida antarctica lipase B as a biocatalyst under mild conditions (42 °C, 3.5 h in dimethyl sulfoxide), methyl benzoylformate was efficiently converted into oximes ether (Z and E isomers with upto 87% and 8% yield respectively) and alkyloximes (Z and E isomer with up to 92% and 0% yield respectively) via reactions with methoxyamine and hydroxylamine, respectively. The enzymatic strategy not only significantly shortens reaction times but also enhances selectivity, favoring the Z isomer over the E isomer due to the enzyme’s active site orientation, which reduces steric hindrance. Furthermore, the method demonstrated improved efficiency compared to traditional chemical synthesis, offering higher yields. Based on the results mechanism was proposed, revealing that the enzyme activates the carbonyl carbon of Compound 1 A, to generate an electrophilic carbon, initiating the reaction. Electron donating groups enhance yield by stabilizing the transition state and improving enzyme-substrate interactions. The enzyme catalysis approach is more environmentally sustainable and scalable, aligning with green chemistry principles and offering a promising alternative for the synthesis of bioactive molecules.

Graphical Abstract