ArticleChemistry (Weinheim an der Bergstrasse, Germany)2022
Rational Tuning of the Reactivity of Three-Membered Heterocycle Ring Openings via S
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Bicyclic Selenenyl Sulfides with Tuned Bioreductive Step Rates Reveal Constraints for Probes Targeting Thioredoxin Reductase.Angewandte Chemie (International ed. in English) · 2025Article
- Understanding the SChemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- TransientSynlett : accounts and rapid communications in synthetic organic chemistry · 2025Article
- Vitamin BOrganic letters · 2025Article
- Elucidating reactive sugar-intermediates by mass spectrometry.Communications chemistry · 2025Review
- Aziridine Group Transfer via TransientJournal of the American Chemical Society · 2024Article
- Masked cerulenin enables a dual-site selective protein crosslink.Chemical science · 2023Article
- Rational Tuning of the Reactivity of Three-Membered Heterocycle Ring Openings via SChemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
The development of small-molecule covalent inhibitors and probes continuously pushes the rapidly evolving field of chemical biology forward. A key element in these molecular tool compounds is the "electrophilic trap" that allows a covalent linkage with the target enzyme. The reactivity of this entity needs to be well balanced to effectively trap the desired enzyme, while not being attacked by off-target nucleophiles. Here we investigate the intrinsic reactivity of substrates containing a class of widely used electrophilic traps, the three-membered heterocycles with a nitrogen (aziridine), phosphorus (phosphirane), oxygen (epoxide) or sulfur atom (thiirane) as heteroatom. Using quantum chemical approaches, we studied the conformational flexibility and nucleophilic ring opening of a series of model substrates, in which these electrophilic traps are mounted on a cyclohexene scaffold (C
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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.