Epoxy Isonitriles, A Unique Class of Antibiotics: Synthesis of Their Metabolites and Biological Investigations
| Autor: | Sara Zahim, Guillaume Ernouf, William M. Wuest, Ingrid K. Wilt |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Staphylococcus aureus
Ketone Swine Metabolite Hydrogen cyanide Microbial Sensitivity Tests 010402 general chemistry 01 natural sciences Biochemistry Article chemistry.chemical_compound Nitriles Animals Organic chemistry Bioorganic chemistry Moiety Molecular Biology chemistry.chemical_classification Biological Products Molecular Structure 010405 organic chemistry Organic Chemistry Stereoisomerism Biological activity Epoxy Ketones Anti-Bacterial Agents 0104 chemical sciences chemistry visual_art visual_art.visual_art_medium Epoxy Compounds Molecular Medicine Antibacterial activity |
| Zdroj: | ChemBioChem. 19:2448-2452 |
| ISSN: | 1439-7633 1439-4227 |
| Popis: | Epoxy isonitrile containing natural products often possess specific and potent antibacterial activity against Gram-positive pathogens. This scaffold, however, is extremely labile under acidic and basic conditions, undergoing a Payne rearrangement to produce a stable epoxy ketone metabolite and releasing hydrogen cyanide. We synthesized and performed biological assays with epoxy ketone containing metabolites and identified that the epoxy isonitrile moiety is pertinent for biological activity. Serendipitously, we discovered an α,β-unsaturated epoxy ketone analogue that exhibited moderate activity against Staphylococcus aureus. |
| Databáze: | OpenAIRE |
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