A high-performance chiral <sup>19</sup>F-labeled probe with an increased structural twisting

Wang, Chenyang; Gu, Guangxing; Zhang, Wei; Wu, Jian; Zhao, Yanchuan

doi:10.1039/d4cc01313a

Cited by 3 publications

(1 citation statement)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Methods such as changing the metal center and modulating the twisting of the probe's backbone have been shown to enhance chiral discrimination capability. 23,24 Despite their effectiveness, these strategies often require the multistep synthesis of new 19 F-labeled probes, which can be labor-intensive. Here, we present a new strategy for rapidly assessing a panel of 19 Flabeled probes with distinct discrimination capabilities through in situ modification via dynamic covalent chemistry (Scheme 1).…”

Section: ■ Introductionmentioning

confidence: 99%

Tailoring the Performance of ¹⁹F-Labeled Probes via Dynamic Covalent Chemistry for Improved Chiral Discrimination

Weng,

Wen,

et al. 2024

Anal. Chem.

View full text Add to dashboard Cite

This work presents a novel strategy for postmodifying probes using dynamic covalent chemistry. Leveraging reversible interactions between boronic acid and diols, we obtained a panel of 19 F-labeled probes with distinct resolving abilities. This approach enables rapid identification of probes with satisfactory performance, streamlining synthesis, and enhancing efficiency in chiral analysis. Our findings demonstrate an exceptional ability to differentiate compounds with distal chirality and challenging aliphatic amines. The postmodified probes also exhibit accuracy and reliability in determining enantiomeric excess, promising advancements in enantio-analysis techniques and chiral discrimination.

show abstract

Section: ■ Introductionmentioning

confidence: 99%

Tailoring the Performance of ¹⁹F-Labeled Probes via Dynamic Covalent Chemistry for Improved Chiral Discrimination

Weng,

Wen,

et al. 2024

Anal. Chem.

View full text Add to dashboard Cite

show abstract

Detection and Differentiation of Amines and N‐Heterocycles via Recognition Enabled Chromatographic ¹⁹F NMR

Gu,

Zeng,

Peng

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

In this study, we successfully employed a 19F‐labeled cyclopalladium probe to achieve simultaneous differentiation and detection of various amines and N‐heterocyclic compounds. This method features a broad detection window, facilitating the discrimination and multi‐component analysis of structural analogs and isomers through the generation of characteristic 19F NMR signals with distinct chemical shifts. The utility of this approach is demonstrated in monitoring chemical reactions and identifying components in food, beverages, and cosmetics.

show abstract

19F-Labeled NMR Probes for the Detection and Discrimination of Nitrogen-Containing Analytes

Zhao,

Gu,

Wang

2024

Synthesis

View full text Add to dashboard Cite

The development of 19F-labeled NMR probes has become a pivotal tool in analytical chemistry. Recent advancements in probe design enable precise identification of nitrogen-containing analytes, significantly enhancing the analysis of these biologically important analytes in complex mixtures. This review highlights recent progress with probes based on covalent derivatization and dynamic exchange strategies, which yield distinct 19F NMR signals for each nitrogen-containing analyte. These strategies facilitate separation-free multicomponent analysis and chiral discrimination. Discussions will cover design principles, scope, limitations, and strategies to enhance sensitivity and resolving ability. By addressing current challenges, 19F-labeled NMR probes hold the potential to revolutionize the detection of biologically relevant molecules, catalyzing new discoveries in chemical and biochemical research.

show abstract

A high-performance chiral ¹⁹F-labeled probe with an increased structural twisting

Abstract: We developed a new strategy to enhance the chiral discrimination capability of 19F-Labeled probes by tuning the torsion angle of the probe's backbone, allowing for the resolution of challenging analytes....

Cited by 3 publications

References 41 publications

Tailoring the Performance of ¹⁹F-Labeled Probes via Dynamic Covalent Chemistry for Improved Chiral Discrimination

Tailoring the Performance of ¹⁹F-Labeled Probes via Dynamic Covalent Chemistry for Improved Chiral Discrimination

Detection and Differentiation of Amines and N‐Heterocycles via Recognition Enabled Chromatographic ¹⁹F NMR

19F-Labeled NMR Probes for the Detection and Discrimination of Nitrogen-Containing Analytes

Contact Info

Product

Resources

About

A high-performance chiral 19F-labeled probe with an increased structural twisting

Abstract: We developed a new strategy to enhance the chiral discrimination capability of 19F-Labeled probes by tuning the torsion angle of the probe's backbone, allowing for the resolution of challenging analytes....

Cited by 3 publications

References 41 publications

Tailoring the Performance of 19F-Labeled Probes via Dynamic Covalent Chemistry for Improved Chiral Discrimination

Tailoring the Performance of 19F-Labeled Probes via Dynamic Covalent Chemistry for Improved Chiral Discrimination

Detection and Differentiation of Amines and N‐Heterocycles via Recognition Enabled Chromatographic 19F NMR

19F-Labeled NMR Probes for the Detection and Discrimination of Nitrogen-Containing Analytes

Contact Info

Product

Resources

About

A high-performance chiral ¹⁹F-labeled probe with an increased structural twisting

Tailoring the Performance of ¹⁹F-Labeled Probes via Dynamic Covalent Chemistry for Improved Chiral Discrimination

Tailoring the Performance of ¹⁹F-Labeled Probes via Dynamic Covalent Chemistry for Improved Chiral Discrimination

Detection and Differentiation of Amines and N‐Heterocycles via Recognition Enabled Chromatographic ¹⁹F NMR