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一种含三唑氨基酸配体的手性金属有机框架材料的构建及其在毛细管电色谱对映体分离中的应用。

Construction of a chiral metal-organic framework material with triazole amino acid ligands and its application in capillary electrochromatography for enantioseparation.

作者信息

Zhu Gege, Wu Dan, Li Xinyu, Ge Li, Qi Li, Chen Qin, Niu Bing, Zhong Dan, Sun Xiaodong

机构信息

Shanghai Engineering Research Center of Organ Repair, Joint International Research Laboratory of Biomaterials and Biotechnology in Organ Repair (Ministry of Education), School of Medicine, Shanghai University, Shanghai 200444, PR China.

Department of Nephrology, First Medical Center of Chinese PLA General Hospital, State Key Laboratory of Kidney Diseases, National Clinical Research Center for Kidney Diseases, Beijing Key Laboratory of Medical Devices and Integrated Traditional Chinese and Western Drug Development for Severe Kidney Diseases, Beijing 100853, PR China.

出版信息

J Chromatogr A. 2025 Sep 13;1758:466177. doi: 10.1016/j.chroma.2025.466177. Epub 2025 Jun 28.

Abstract

Chiral separation is vital in medicine because the two versions of a chiral drug can act differently, and one might cause toxicity. Therefore, efficient enantioseparation is essential in pharmaceutical quality control. In this study, we modified the amino site of l-lysine (L-Lys) with a triazole ring. The triazole amino acid ligand (NL) with self-assembly potential was designed independently. Then NLMOF was synthesized by coordination with Cu (II) under green ambient stirring conditions. The NLMOF (triazole-modified metal-organic framework) was uniformly integrated into a capillary column through a post-modification method and utilized in open tubular capillary electrochromatography (OT-CEC) for enantioseparation. 10 chiral amino acids and 1 chiral drug was successfully separated in NLMOF@OT-CEC method with excellent repeatability (RSD < 5 %) and stability (cycles > 100). Furthermore, when compared with similar MOFs (metal-organic frameworks) chiral stationary phase, NLMOF demonstrates advantages in terms of mild preparation conditions, cost-effectiveness, and environmental sustainability, making it a promising candidate for industrial-scale production.

摘要

手性分离在医学领域至关重要,因为手性药物的两种对映体可能具有不同的作用,其中一种可能会导致毒性。因此,高效的对映体分离在药物质量控制中至关重要。在本研究中,我们用三唑环修饰了L-赖氨酸(L-Lys)的氨基位点。独立设计了具有自组装潜力的三唑氨基酸配体(NL)。然后在绿色环境搅拌条件下,通过与Cu(II)配位合成了NLMOF。通过后修饰方法将NLMOF(三唑修饰的金属有机框架)均匀地整合到毛细管柱中,并用于开管毛细管电色谱(OT-CEC)进行对映体分离。在NLMOF@OT-CEC方法中成功分离了10种手性氨基酸和1种手性药物,具有出色的重复性(RSD < 5%)和稳定性(循环次数>100)。此外,与类似的金属有机框架(MOF)手性固定相相比,NLMOF在制备条件温和、成本效益和环境可持续性方面表现出优势,使其成为工业规模生产的有前途的候选者。

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