Literature DB >> 24719396

Noncovalent chirality sensing ensembles for the detection and reaction monitoring of amino acids, peptides, proteins, and aromatic drugs.

Frank Biedermann1, Werner M Nau.   

Abstract

Ternary complexes between the macrocyclic host cucurbit[8]uril, dicationic dyes, and chiral aromatic analytes afford strong induced circular dichroism (ICD) signals in the near-UV and visible regions. This allows for chirality sensing and peptide-sequence recognition in water at low micromolar analyte concentrations. The reversible and noncovalent mode of binding ensures an immediate response to concentration changes, which allows the real-time monitoring of chemical reactions. The introduced supramolecular method is likely to find applications in bioanalytical chemistry, especially enzyme assays, for drug-related analytical applications, and for continuous monitoring of enantioselective reactions, particularly asymmetric catalysis.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  circular dichroism; cucurbiturils; dyes; macrocycles; sequence recognition; supramolecular chemistry

Mesh:

Substances:

Year:  2014        PMID: 24719396     DOI: 10.1002/anie.201400718

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  19 in total

Review 1.  Molecular Probes, Chemosensors, and Nanosensors for Optical Detection of Biorelevant Molecules and Ions in Aqueous Media and Biofluids.

Authors:  Joana Krämer; Rui Kang; Laura M Grimm; Luisa De Cola; Pierre Picchetti; Frank Biedermann
Journal:  Chem Rev       Date:  2022-01-07       Impact factor: 60.622

2.  Five-Component Self-Assembly of Cucurbituril-Based Hetero-pseudorotaxanes.

Authors:  Cátia Parente Carvalho; Zoe Domínguez; Cristina Domínguez; Hamdy S El-Sheshtawy; José Paulo Da Silva; Jesús F Arteaga; Uwe Pischel
Journal:  ChemistryOpen       Date:  2017-03-10       Impact factor: 2.911

3.  Click chemistry enables quantitative chiroptical sensing of chiral compounds in protic media and complex mixtures.

Authors:  F Yushra Thanzeel; Kaluvu Balaraman; Christian Wolf
Journal:  Nat Commun       Date:  2018-12-14       Impact factor: 14.919

Review 4.  Applications of Cucurbiturils in Medicinal Chemistry and Chemical Biology.

Authors:  Debapratim Das; Khaleel I Assaf; Werner M Nau
Journal:  Front Chem       Date:  2019-09-13       Impact factor: 5.221

5.  A rapid and sensitive method for chiroptical sensing of α-amino acids via click-like labeling with o-phthalaldehyde and p-toluenethiol.

Authors:  Bo Li; Jie Zhang; Li Li; Gong Chen
Journal:  Chem Sci       Date:  2020-12-22       Impact factor: 9.825

6.  Elucidating dissociation activation energies in host-guest assemblies featuring fast exchange dynamics.

Authors:  Ronit Shusterman-Krush; Laura Grimm; Liat Avram; Frank Biedermann; Amnon Bar-Shir
Journal:  Chem Sci       Date:  2020-12-08       Impact factor: 9.825

7.  Fluorescence detected circular dichroism (FDCD) for supramolecular host-guest complexes.

Authors:  Amrutha Prabodh; Yichuan Wang; Stephan Sinn; Paolo Albertini; Christian Spies; Eduard Spuling; Liu-Pan Yang; Wei Jiang; Stefan Bräse; Frank Biedermann
Journal:  Chem Sci       Date:  2021-06-09       Impact factor: 9.825

8.  Rapid organocatalytic chirality analysis of amines, amino acids, alcohols, amino alcohols and diols with achiral iso(thio)cyanate probes.

Authors:  Eryn Nelson; Jeffrey S S K Formen; C Wolf
Journal:  Chem Sci       Date:  2021-05-25       Impact factor: 9.825

9.  Complexation of chiral amines by resorcin[4]arene sulfonic acids in polar media - circular dichroism and diffusion studies of chirality transfer and solvent dependence.

Authors:  Bartosz Setner; Agnieszka Szumna
Journal:  Beilstein J Org Chem       Date:  2019-08-12       Impact factor: 2.883

10.  Rapid chiral analysis based on liquid-phase cyclic chemiluminescence.

Authors:  Runkun Zhang; Yanhui Zhong; Zhenyu Lu; Yanlong Chen; Gongke Li
Journal:  Chem Sci       Date:  2020-10-22       Impact factor: 9.825

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