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αβ,α′β′-Diepoxyketones are mechanism-based inhibitors of nucleophilic cysteine enzymes
Epoxides are an established class of electrophilic alkylating agents that react with nucleophilic protein residues. We report αβ,α′β′-diepoxyketones (DEKs) as a new type of mechanism-based inhibitors of nucleophilic cysteine enzymes. Studies with the l,d-transpeptidase Ldt(Mt2) from Mycobacterium tu...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10601815/ https://www.ncbi.nlm.nih.gov/pubmed/37815791 http://dx.doi.org/10.1039/d3cc02932h |
Sumario: | Epoxides are an established class of electrophilic alkylating agents that react with nucleophilic protein residues. We report αβ,α′β′-diepoxyketones (DEKs) as a new type of mechanism-based inhibitors of nucleophilic cysteine enzymes. Studies with the l,d-transpeptidase Ldt(Mt2) from Mycobacterium tuberculosis and the main protease from SARS-CoV-2 (M(pro)) reveal that following epoxide ring opening by a nucleophilic cysteine, further reactions can occur, leading to irreversible alkylation. |
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