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基于对映体识别亲脂性液膜的高通量纳摩尔级手性砌块对映体富集分析方法

Enantiodiscriminating Lipophilic Liquid Membrane-Based Assay for High-Throughput Nanomolar Enantioenrichment of Chiral Building Blocks.

作者信息

Jávor Bálint, Vezse Panna, Golcs Ádám, Huszthy Péter, Tóth Tünde

机构信息

Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4, H-1111 Budapest, Hungary.

Centre for Energy Research, Konkoly-Thege Miklós út 29-33, H-1121 Budapest, Hungary.

出版信息

Membranes (Basel). 2023 Jan 11;13(1):94. doi: 10.3390/membranes13010094.

DOI:10.3390/membranes13010094
PMID:36676901
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9862411/
Abstract

The reported optical resolution method was designed to support high-throughput enantioseparation of molecular building blocks obtained by automated small-scale synthetic methods. Lipophilic esters of common resolving agents were prepared and used as liquid membranes on the indifferent polymer surface of a microtiter assay. Chiral model compounds were enriched in one of the enantiomers starting from the aqueous solutions of their racemic mixture. Enantiodiscrimination was provided by forming diastereomeric coordination complexes of lipophilic enantiopure esters with the enantiomers of the chiral building blocks inside the liquid membranes. This enantiomeric recognition resulted in a greater distribution ratio of the preferred isomer in the membrane phase, thus the process enables a simultaneous enantioenrichment of the solutions outside the membrane. This paper reports a novel microplate-integrated stereoselective membrane enrichment technique satisfying the need for automatable enantioseparation on a subpreparative scale.

摘要

所报道的光学拆分方法旨在支持通过自动化小规模合成方法获得的分子构建块的高通量对映体分离。制备了常见拆分剂的亲脂性酯,并将其用作微量滴定分析中惰性聚合物表面的液膜。手性模型化合物从其外消旋混合物的水溶液开始,在其中一种对映体中富集。通过在液膜内形成亲脂性对映体纯酯与手性构建块对映体的非对映体配位络合物来实现对映体识别。这种对映体识别导致优选异构体在膜相中的分配比更大,因此该过程能够同时对膜外溶液进行对映体富集。本文报道了一种新型的微孔板集成立体选择性膜富集技术,满足了亚制备规模自动对映体分离的需求。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e7d3/9862411/d907d6224de0/membranes-13-00094-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e7d3/9862411/79ef9c36ebaf/membranes-13-00094-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e7d3/9862411/7c0abc8191d0/membranes-13-00094-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e7d3/9862411/75b9ec55e0f8/membranes-13-00094-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e7d3/9862411/6a1012e8173c/membranes-13-00094-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e7d3/9862411/d907d6224de0/membranes-13-00094-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e7d3/9862411/79ef9c36ebaf/membranes-13-00094-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e7d3/9862411/7c0abc8191d0/membranes-13-00094-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e7d3/9862411/75b9ec55e0f8/membranes-13-00094-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e7d3/9862411/6a1012e8173c/membranes-13-00094-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e7d3/9862411/d907d6224de0/membranes-13-00094-g004.jpg

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本文引用的文献

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J Chromatogr A. 2022 Aug 16;1677:463305. doi: 10.1016/j.chroma.2022.463305. Epub 2022 Jul 3.
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Chiral fluorescence recognition of glutamine enantiomers by a modified Zr-based MOF based on solvent-assisted ligand incorporation.基于溶剂辅助配体掺入的改性锆基金属有机框架对手性谷氨酰胺对映体的荧光识别
RSC Adv. 2021 Nov 23;11(59):37584-37594. doi: 10.1039/d1ra06857a. eCollection 2021 Nov 17.
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Homochiral Metal-Organic Framework Based Mixed Matrix Membrane for Chiral Resolution.
用于手性拆分的基于同手性金属有机框架的混合基质膜
Membranes (Basel). 2022 Mar 24;12(4):357. doi: 10.3390/membranes12040357.
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Enantioselective UHPLC Screening Combined with Modeling for Streamlined Development of Ultrafast Enantiopurity Assays.对映体选择性 UHPLC 筛选结合建模,用于超快速对映体纯度分析的简化开发。
Anal Chem. 2022 Jan 25;94(3):1804-1812. doi: 10.1021/acs.analchem.1c04585. Epub 2021 Dec 21.
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Enantioselective Mixed Matrix Membranes for Chiral Resolution.用于手性拆分的对映选择性混合基质膜
Membranes (Basel). 2021 Apr 10;11(4):279. doi: 10.3390/membranes11040279.
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Novel approaches for biomolecule immobilization in microscale systems.微尺度系统中生物分子固定化的新方法。
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