A chiral metal-organic framework {(HQA)(ZnCl(2))(2.5H(2)O)}(n) for the enantioseparation of chiral amino acids and drugs.

A chiral metal-organic framework {(HQA)(ZnCl(2))(2.5H(2)O)}(n) for the enantioseparation of chiral amino acids and drugs.
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DOI:
10.1016/j.jpha.2023.03.003
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发表时间:
2023-04
影响因子:
8.8
通讯作者:
Sun, Xiaodong
Sun, Xiaodong
中科院分区:
医学1区
文献类型:
--
作者:
Zheng, Xiangtai;Zhang, Qi;Ma, Qianjie;Li, Xinyu;Zhao, Liang;Sun, Xiaodong

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具有对映体亚基的手性金属有机骨架(CMOFs)在手性化学中有广泛的应用。以6-甲氧基-(8S,9R)-金鸡碱-9-醇-3-羧酸(HQA)和ZnCl2, {(HQA)(ZnCl2)(2.5H2O)}n为固定相,通过原位制备方法构建了cof,首次用于手性氨基酸和药物分析。采用扫描电镜、x射线衍射、傅里叶变换红外光谱、圆二色性、x射线光电子能谱、热重分析和brunauer - emmet - teller表面积测量等一系列分析技术,对{(HQA)(ZnCl2)(2.5H2O)}n纳米晶体及其对应的手性固定相进行了系统表征。在开管毛细管电色谱(CEC)中,新型手性色谱柱对多种手性分析物,包括19种外消旋丹酰氨基酸和几种模型手性药物(酸性和碱性),具有较强的对映选择性。对手性CEC条件进行了优化,并对其对映体分离机理进行了探讨。本研究不仅引入了mof型CSP家族的一个新的高效成员,而且充分利用多孔有机框架的固有特性,展示了提高传统手性识别试剂对映选择性的潜力。制备了{(HQA)(ZnCl2)(2.5H2O)}n作为OT-CEC对映体分离的新型手性固定相。采用多种表征方法对MOF和MOF涂层毛细管进行了表征。mof包被的毛细管对几种外消旋氨基酸和药物具有很高的对映选择性。
Chiral metal-organic frameworks (CMOFs) with enantiomeric subunits have been employed in chiral chemistry. In this study, a CMOF formed from 6-methoxyl-(8S,9R)-cinchonan-9-ol-3-carboxylic acid (HQA) and ZnCl2, {(HQA)(ZnCl2)(2.5H2O)}n, was constructed as a chiral stationary phase (CSP) via an in situ fabrication approach and used for chiral amino acid and drug analyses for the first time. The {(HQA)(ZnCl2)(2.5H2O)}n nanocrystal and the corresponding chiral stationary phase were systematically characterised using a series of analytical techniques including scanning electron microscopy, X-ray diffraction, Fourier transform infrared spectroscopy, circular dichroism, X-ray photoelectron spectroscopy, thermogravimetric analysis, and Brunauer-Emmett-Teller surface area measurements. In open-tubular capillary electrochromatography (CEC), the novel chiral column exhibited strong and broad enantioselectivity toward a variety of chiral analytes, including 19 racemic dansyl amino acids and several model chiral drugs (both acidic and basic). The chiral CEC conditions were optimised, and the enantioseparation mechanisms are discussed. This study not only introduces a new high-efficiency member of the MOF-type CSP family but also demonstrates the potential of improving the enantioselectivities of traditional chiral recognition reagents by fully using the inherent characteristics of porous organic frameworks. {(HQA)(ZnCl2)(2.5H2O)}n was prepared as a novel chiral stationary phase for OT-CEC for enantioseparation. Numerous characterization methods were applied to characterize the MOF and MOF-coated capillary. MOF-coated capillary exhibited high enantioselecivity for several racemic amino acids and drugs.
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