ArticleMolecules (Basel, Switzerland)2017
Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling.
Article in Molecules (Basel, Switzerland), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- The Versatility of Diazirines: Properties, Synthetic and Modern Applications.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Design, synthesis and modelling of photoreactive chemical probes for investigating target engagement of plasmepsin IX and X inRSC chemical biology · 2024Article
- A clickable photoaffinity probe of betulinic acid identifies tropomyosin as a target.Acta pharmaceutica Sinica. B · 2022Article
- Emerging Applications of Aryl Trifluoromethyl Diazoalkanes and Diazirines in Synthetic Transformations.ACS organic & inorganic Au · 2022Review
- New Trends in Diaziridine Formation and Transformation (a Review).Molecules (Basel, Switzerland) · 2021Review
- Recent Advances in Chemical Biology Using Benzophenones and Diazirines as Radical Precursors.Molecules (Basel, Switzerland) · 2020Review
- Current advances of carbene-mediated photoaffinity labeling in medicinal chemistry.RSC advances · 2018Review
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Authors and funding
7 authors.
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Abstract
Aliphatic diazirines have been widely used as prominent photophores for photoaffinity labeling owing to their relatively small size which can reduce the steric effect on the natural interaction between ligands and proteins. Based on our continuous efforts to develop efficient methods for the synthesis of aliphatic diazirines, we present here a comprehensive study about base-mediated one-pot synthesis of aliphatic diazirines. It was found that potassium hydroxide (KOH) can also promote the construction of aliphatic diazirine with good efficiency. Importantly, KOH is cheaper, highly available, and easily handled and stored compared with the previously used base, potassium tert-butoxide (t-BuOK). Gram-scale study showed that it owned great advantages in being used for the large-scale production of aliphatic diazirines. This protocol is highly neat and the desired products can be easily isolated and purified. As the first comprehensive study of the base-mediated one-pot synthesis of aliphatic diazirines, this work provided good insight into the preparation and utilization of diazirine-based photoaffinity labeling probes.
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