Biocatalytic syn-stereoselective synthesis of alkyloxime, oxime ether, and their derivatives
文献类型：期刊论文
| 作者 | Khan, Taimur1,2; Bahadar, Khan3; Khan, Maaz1,4; Hanzi, Gao2; Shahab, Muhammad5; Zheng, Guojun2 |
| 刊名 | BIOTECHNOLOGY AND BIOPROCESS ENGINEERING
 |
| 出版日期 | 2025-11-21 |
| 页码 | 10 |
| 关键词 | Enzyme catalysis
Chemoselectivity
Alkyl oxime
Oxime derivatives
|
| ISSN号 | 1226-8372 |
| DOI | 10.1007/s12257-025-00238-2 |
| 英文摘要 | 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 degrees 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. |
| WOS关键词 | LIPASE-B |
| 资助项目 | State Key Laboratory of Chemical Resource Engineering[(No. 2021YFC2102900, No. 2021YFC2101503)] |
| WOS研究方向 | Biotechnology & Applied Microbiology |
| 语种 | 英语 |
| WOS记录号 | WOS:001619892000001 |
| 出版者 | KOREAN SOC BIOTECHNOLOGY & BIOENGINEERING |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/321992]  |
| 专题 | 国家级研究中心_原创新药研究全国重点实验室 |
| 通讯作者 | Zheng, Guojun |
| 作者单位 | 1.Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan 528400, Peoples R China 2.Beijing Univ Chem Technol, Coll Life Sci, State Key Lab Chem Resources Engn, Beijing 100029, Peoples R China 3.Beijing Univ Chem Technol, State Key Lab Chem Resource Engn, Beijing, Peoples R China 4.Univ Chinese Acad Sci, State Key Lab Drug Res, Beijing 100049, Peoples R China 5.Guangdong Med Univ, Dongguan Affiliated Hosp 1, Dongguan Key Lab Comp Aided Drug Design, Dongguan 523710, Peoples R China |
| 推荐引用方式 GB/T 7714 | Khan, Taimur,Bahadar, Khan,Khan, Maaz,et al. Biocatalytic syn-stereoselective synthesis of alkyloxime, oxime ether, and their derivatives[J]. BIOTECHNOLOGY AND BIOPROCESS ENGINEERING,2025:10. |
| APA | Khan, Taimur,Bahadar, Khan,Khan, Maaz,Hanzi, Gao,Shahab, Muhammad,&Zheng, Guojun.(2025).Biocatalytic syn-stereoselective synthesis of alkyloxime, oxime ether, and their derivatives.BIOTECHNOLOGY AND BIOPROCESS ENGINEERING,10. |
| MLA | Khan, Taimur,et al."Biocatalytic syn-stereoselective synthesis of alkyloxime, oxime ether, and their derivatives".BIOTECHNOLOGY AND BIOPROCESS ENGINEERING (2025):10. |
入库方式： OAI收割
来源：上海药物研究所
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