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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 \u03b1,\u03b2\u2010unsaturated epoxy ketone analogue that exhibited moderate activity against\n                    <jats:italic>Staphylococcus aureus<\/jats:italic>\n                    .\n                  <\/jats:p>","DOI":"10.1002\/cbic.201800550","type":"journal-article","created":{"date-parts":[[2018,10,2]],"date-time":"2018-10-02T09:36:20Z","timestamp":1538472980000},"page":"2448-2452","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Epoxy Isonitriles, A Unique Class of Antibiotics: Synthesis of Their Metabolites and Biological Investigations"],"prefix":"10.1002","volume":"19","author":[{"given":"Guillaume","family":"Ernouf","sequence":"first","affiliation":[{"name":"Department of Chemistry Emory University  Atlanta Georgia 30322 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ingrid K.","family":"Wilt","sequence":"additional","affiliation":[{"name":"Department of Chemistry Emory University  Atlanta Georgia 30322 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sara","family":"Zahim","sequence":"additional","affiliation":[{"name":"Department of Chemistry Emory University  Atlanta Georgia 30322 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5198-7744","authenticated-orcid":false,"given":"William M.","family":"Wuest","sequence":"additional","affiliation":[{"name":"Department of Chemistry Emory University  Atlanta Georgia 30322 USA"},{"name":"Emory Antibiotic Resistance Center Emory University  Atlanta Georgia 30322 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,10,31]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00283"},{"key":"e_1_2_2_2_1","unstructured":"\u00a0"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201506818"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201506818"},{"key":"e_1_2_2_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201506818"},{"key":"e_1_2_2_5_1","unstructured":"\u00a0"},{"key":"e_1_2_2_6_2","unstructured":"W.-C.Liu W. 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