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基于MOF-on-MOF固定相的涂层毛细管电色谱法对手性苯基芳香族化合物的对映体分析

Enantiomeric analysis of chiral phenyl aromatic compounds by coated capillary electrochromatography based on a MOF-on-MOF stationary phase.

作者信息

Miao Pandeng, Chen Jiaquan, Xu Guangfu, Yu Tao, Du Yingxiang

机构信息

Key Laboratory of Drug Quality Control and Pharmacovigilance (Ministry of Education), China Pharmaceutical University, Nanjing, 210009, People's Republic of China.

State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 210009, People's Republic of China.

出版信息

Mikrochim Acta. 2024 Feb 27;191(3):160. doi: 10.1007/s00604-024-06243-1.

Abstract

Chiral phenyl aromatic compounds (CPACs) are widely used in drug development, food/cosmetic production, and other organic synthesis processes, and their different enantiomers have distinct physiological activities and application differences. A double-layer metal-organic framework composite (MOF-on-MOF) was obtained by in situ synthesis of chiral metal-organic framework (CMOM-3S) on the surface of an iron-based metal-organic framework (NH-MIL-101(Fe)). According to our investigation, MOF-on-MOF composite was for the first time applied to the stationary phase of capillary electrochromatography (CEC), and enantioseparations of eight CPACs were accomplished. Compared with single CMOM-3S, the enantioseparation performance of the coated capillary columns based on NH-MIL-101(Fe)@CMOM-3S was improved by 34.07 ~ 720.0%. The R-/S-mandelic acid in actual sample (apricot leaves) was detected by the newly CEC system to be 0.0118 mg mL and 0.0523 mg mL, respectively. The spike recoveries were 96.60 ~ 104.7%, indicating its good stability and accuracy. In addition, the selective adsorption capacity of MOF-on-MOF composites was verified by adsorption experiments.

摘要

手性苯基芳香族化合物(CPACs)广泛应用于药物开发、食品/化妆品生产及其他有机合成过程,其不同对映体具有不同的生理活性和应用差异。通过在铁基金属有机框架(NH-MIL-101(Fe))表面原位合成手性金属有机框架(CMOM-3S),得到了一种双层金属有机框架复合材料(MOF-on-MOF)。据我们调查,MOF-on-MOF复合材料首次应用于毛细管电色谱(CEC)固定相,并完成了8种CPACs的对映体分离。与单一的CMOM-3S相比,基于NH-MIL-101(Fe)@CMOM-3S的涂层毛细管柱的对映体分离性能提高了34.07 ~ 720.0%。利用新的CEC系统检测实际样品(杏叶)中的R-/S-扁桃酸,含量分别为0.0118 mg mL和0.0523 mg mL。加标回收率为96.60 ~ 104.7%,表明其具有良好的稳定性和准确性。此外,通过吸附实验验证了MOF-on-MOF复合材料的选择性吸附能力。

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