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利用可见光区域的圆二色性诱导对手性羧酸对映体进行分子传感

Molecular Sensing of Chiral Carboxylic Acid Enantiomers Using CD Inductions in the Visible Light Region.

作者信息

Formen Jeffrey S S K, Nelson Eryn, Wolf Christian

机构信息

Chemistry Department, Georgetown University, Washington, D.C. 20057, United States.

出版信息

J Org Chem. 2025 Jan 17;90(2):994-1000. doi: 10.1021/acs.joc.4c02055. Epub 2025 Jan 2.

DOI:10.1021/acs.joc.4c02055
PMID:39745140
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11744787/
Abstract

The reaction between a chiral carboxylic acid molecule and 1,1'-bis(diphenylphosphino)ferrocenepalladium dichloride in the presence of a mild base generates a chiroptically active metal complex displaying strong circular dichroism (CD) signals in the visible light region, a highly sought-after goal in the optical sensing realm. The molecular recognition process is complete within a few minutes and can be used for fast chiroptical determination of the enantiomeric composition and concentration of carboxylic acid samples. This method is operationally simple and broadly applicable to a large variety of structures including important drugs, natural products, amino acids, and hydroxy acids. All components needed are commercially available, and this optical sensing assay can be readily adapted by any laboratory interested in chirality analysis and high-throughput experimentation.

摘要

在温和碱存在的情况下,手性羧酸分子与二氯双(二苯基膦基)二茂铁钯之间的反应会生成一种在手性光学上具有活性的金属配合物,该配合物在可见光区域显示出强烈的圆二色性(CD)信号,这是光学传感领域一个备受追捧的目标。分子识别过程在几分钟内即可完成,可用于快速手性光学测定羧酸样品的对映体组成和浓度。该方法操作简单,广泛适用于多种结构,包括重要药物、天然产物、氨基酸和羟基酸。所需的所有组分均可从商业渠道获得,任何对手性分析和高通量实验感兴趣的实验室都可轻松采用这种光学传感测定方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b30a/11744787/823552be18fc/jo4c02055_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b30a/11744787/eed0ad2ed8d0/jo4c02055_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b30a/11744787/f40cc9028359/jo4c02055_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b30a/11744787/823552be18fc/jo4c02055_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b30a/11744787/eed0ad2ed8d0/jo4c02055_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b30a/11744787/f40cc9028359/jo4c02055_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b30a/11744787/823552be18fc/jo4c02055_0003.jpg

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本文引用的文献

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Chirality Sensing of Chiral Carboxylic Acids by a Ureido-Linked Zinc Bisporphyrinate.脲基连接的双锌卟啉对手性羧酸的手性传感
Chem Asian J. 2024 Jul 15;19(14):e202400359. doi: 10.1002/asia.202400359. Epub 2024 Jun 19.
2
Circular Dichroism Sensing: Strategies and Applications.圆二色光谱传感:策略与应用
Angew Chem Int Ed Engl. 2024 May 6;63(19):e202400767. doi: 10.1002/anie.202400767. Epub 2024 Mar 14.
3
Determination of Enantiomeric Excess and Diastereomeric Excess via Optical Methods. Application to α-methyl-β-hydroxy-carboxylic acids.
通过光学方法测定对映体过量和非对映体过量。应用于α-甲基-β-羟基羧酸。
Org Chem Front. 2023 Mar 21;10(6):1386-1392. doi: 10.1039/d2qo01444k. Epub 2023 Jan 25.
4
Biomacromolecule-Assisted Screening for Reaction Discovery and Catalyst Optimization.生物大分子辅助的反应发现和催化剂优化筛选。
Chem Rev. 2022 Aug 24;122(16):13800-13880. doi: 10.1021/acs.chemrev.2c00213. Epub 2022 Jul 29.
5
Chiroptical Enhancement of Chiral Dicarboxylic Acids from Confinement in a Stereodynamic Supramolecular Cage.受限在立体动力学超分子笼中对手性二羧酸的手性光增强效应
ACS Sens. 2022 May 27;7(5):1390-1394. doi: 10.1021/acssensors.2c00038. Epub 2022 Apr 26.
6
Chiral analysis of pantolactone with molecular rotational resonance spectroscopy.手性分析泮托拉唑的分子旋转共振光谱法。
Chirality. 2022 Jan;34(1):114-125. doi: 10.1002/chir.23379. Epub 2021 Oct 26.
7
Chiroptical Switching and Quantitative Chirality Sensing with (Pseudo)halogenated Quinones.手性光学开关和(拟)卤代醌的定量手性传感。
Angew Chem Int Ed Engl. 2021 Dec 20;60(52):27031-27038. doi: 10.1002/anie.202111542. Epub 2021 Nov 18.
8
Fluorescence detected circular dichroism (FDCD) for supramolecular host-guest complexes.超分子主客体复合物的荧光检测圆二色性(FDCD)
Chem Sci. 2021 Jun 9;12(27):9420-9431. doi: 10.1039/d1sc01411k. eCollection 2021 Jul 14.
9
Rapid organocatalytic chirality analysis of amines, amino acids, alcohols, amino alcohols and diols with achiral iso(thio)cyanate probes.使用非手性异(硫)氰酸酯探针快速进行胺、氨基酸、醇、氨基醇和二醇的有机催化手性分析。
Chem Sci. 2021 May 25;12(25):8784-8790. doi: 10.1039/d1sc02061g. eCollection 2021 Jul 1.
10
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Chem Sci. 2020 Dec 22;12(7):2504-2508. doi: 10.1039/d0sc05749e.