He Wu, Yong Wang, Guangguang Yang, Karuppu Selvaraj, Gang Chen
{"title":"Biomimetic oxidation of tetracycline and derivatives at C11a","authors":"He Wu, Yong Wang, Guangguang Yang, Karuppu Selvaraj, Gang Chen","doi":"10.1016/j.tetlet.2024.155366","DOIUrl":null,"url":null,"abstract":"<div><div>Tetracycline destructases (TDases), a type of TC-inactivating enzymes, inactivate all known TC antibiotics by C11a oxidation, which is considered as a clinical threat. To provide more information on this enzymatic inactivation and oxygenated TCs, we report here a chemical oxidation of Tetracycline and its derivatives at the C11a position using <em>m</em>-CPBA with additives via biomimetic pathways. The structures of the oxygen-containing TCs (<strong>2h, 2i</strong>) were confirmed by X-ray analysis, and further transformations were performed with oxygen-containing TCs (<strong>2e</strong>, <strong>2i</strong>).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155366"},"PeriodicalIF":1.5000,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924004611","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Tetracycline destructases (TDases), a type of TC-inactivating enzymes, inactivate all known TC antibiotics by C11a oxidation, which is considered as a clinical threat. To provide more information on this enzymatic inactivation and oxygenated TCs, we report here a chemical oxidation of Tetracycline and its derivatives at the C11a position using m-CPBA with additives via biomimetic pathways. The structures of the oxygen-containing TCs (2h, 2i) were confirmed by X-ray analysis, and further transformations were performed with oxygen-containing TCs (2e, 2i).
期刊介绍：
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.
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