ArticleAngewandte Chemie (International ed. in English)2020
Single-Molecule Observation of Intermediates in Bioorthogonal 2-Cyanobenzothiazole Chemistry.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
What it found
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Who cites it
10 citing papers in PubMed, 25 citations in OpenAlex.
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- Real-Time Visualisation of Reaction Kinetics and Dynamics: Single-Molecule Insights into the Iminium-Catalysed Diels-Alder Reaction.Angewandte Chemie (International ed. in English) · 2025Article
- Native globular ferritin nanopore sensor.Nature communications · 2025Article
- Nanopores Reveal the Stoichiometry of Single Oligoadenylates Produced by Type III CRISPR-Cas.ACS nano · 2024Article
- Local and Sustained Baricitinib Delivery to the Skin through Injectable Hydrogels Containing Reversible Thioimidate Adducts.Advanced healthcare materials · 2024Article
- The Nitrile Bis-Thiol Bioconjugation Reaction.Journal of the American Chemical Society · 2024Article
- Functionalised nanopores: chemical and biological modifications.Chemical science · 2022Review
- Pnictogen-Bonding Catalysis and Transport Combined: Polyether Transporters Made In Situ.JACS Au · 2021Article
- The chronological evolution of small organic molecular fluorescent probes for thiols.Chemical science · 2020Review
- Single-Molecule Observation of Intermediates in Bioorthogonal 2-Cyanobenzothiazole Chemistry.Angewandte Chemie (International ed. in English) · 2020Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We report a single-molecule mechanistic investigation into 2-cyanobenzothiazole (CBT) chemistry within a protein nanoreactor. When simple thiols reacted reversibly with CBT, the thioimidate monoadduct was approximately 80-fold longer-lived than the tetrahedral bisadduct, with important implications for the design of molecular walkers. Irreversible condensation between CBT derivatives and N-terminal cysteine residues has been established as a biocompatible reaction for site-selective biomolecular labeling and imaging. During the reaction between CBT and aminothiols, we resolved two transient intermediates, the thioimidate and the cyclic precursor of the thiazoline product, and determined the rate constants associated with the stepwise condensation, thereby providing critical information for a variety of applications, including the covalent inhibition of protein targets and dynamic combinatorial chemistry.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.