ArticleChembiochem : a European journal of chemical biology2017
Selective Covalent Protein Modification by 4-Halopyridines through Catalysis.
Article in Chembiochem : a European journal of chemical biology, 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, 15 citations in OpenAlex.
- Discovery of a Tunable Heterocyclic Electrophile 4-Chloro-pyrazolopyridine That Defines a Unique Subset of Ligandable Cysteines.ACS chemical biology · 2024Article
- Proximity-Dependent Labeling of Cysteines.Journal of the American Chemical Society · 2021Article
- Inhibition mechanism of SARS-CoV-2 main protease by ebselen and its derivatives.Nature communications · 2021Article
- Selective USP7 inhibition elicits cancer cell killing through a p53-dependent mechanism.Scientific reports · 2020Article
- Development of a Suicide Inhibition-Based Protein Labeling Strategy for Nicotinamide N-Methyltransferase.ACS chemical biology · 2019Article
- The Taxonomy of Covalent Inhibitors.Biochemistry · 2018Review
- "Inverse Drug Discovery" Strategy To Identify Proteins That Are Targeted by Latent Electrophiles As Exemplified by Aryl Fluorosulfates.Journal of the American Chemical Society · 2018Article
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Authors and funding
5 authors at 2 institutions in 1 country.
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Abstract
We have investigated 4-halopyridines as selective, tunable, and switchable covalent protein modifiers for use in the development of chemical probes. Nonenzymatic reactivity of 4-chloropyridine with amino acids and thiols was ranked with respect to common covalent protein-modifying reagents and found to have reactivity similar to that of acrylamide, but could be switched to a reactivity similar to that of iodoacetamide upon stabilization of the positively charged pyridinium. Diverse, fragment-sized 4-halopyridines inactivated human dimethylarginine dimethylaminohydrolase-1 (DDAH1) through covalent modification of the active site cysteine, acting as quiescent affinity labels that required off-pathway catalysis through stabilization of the protonated pyridinium by a neighboring aspartate residue. A series of 2-fluoromethyl-substituted 4-chloropyridines demonstrated that the pK
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