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Amino-Based Probe for Natural Products with Covalent Binding Ability to Lysine and Mechanism of Action of Medermycin
Organic Letters ( IF 4.9 ) Pub Date : 2024-11-19 , DOI: 10.1021/acs.orglett.4c03803 Jiaxu Shang, Shupeng Yin, Jingjing Shen, Chao Gao, Weihong Wang, Ke Sun, Weiming Zhu, Peng Fu
Organic Letters ( IF 4.9 ) Pub Date : 2024-11-19 , DOI: 10.1021/acs.orglett.4c03803 Jiaxu Shang, Shupeng Yin, Jingjing Shen, Chao Gao, Weihong Wang, Ke Sun, Weiming Zhu, Peng Fu
A chemoselective amino-based probe was designed for discovering natural products with covalent binding potential to lysine. Using this reactivity-based technique, a marine-derived Streptomyces strain was identified, which could produce medermycin as the major metabolite. A new compound, mederpyrrole A, derived from medermycin and anthranilic acid through nonenzymatic reaction was isolated. Medermycin can react with primary amines under mild conditions to generate chimeric products possessing a naphthoquinone-pyrrole skeleton. It can also covalently bind to proteins.
中文翻译:
与赖氨酸具有共价结合能力的天然产物氨基探针及美德霉素的作用机制
设计了一种基于化学选择性氨基的探针,用于发现与赖氨酸具有共价结合潜力的天然产物。使用这种基于反应性的技术,鉴定了一种海洋来源的链霉菌菌株,它可以产生美得霉素作为主要代谢物。通过非酶反应从美得霉素和邻氨基苯甲酸分离出一种新化合物 mederpyrrole A。美德霉素可在温和条件下与伯胺反应,生成具有萘醌-吡咯骨架的嵌合产物。它还可以与蛋白质共价结合。
更新日期:2024-11-19
中文翻译:
与赖氨酸具有共价结合能力的天然产物氨基探针及美德霉素的作用机制
设计了一种基于化学选择性氨基的探针,用于发现与赖氨酸具有共价结合潜力的天然产物。使用这种基于反应性的技术,鉴定了一种海洋来源的链霉菌菌株,它可以产生美得霉素作为主要代谢物。通过非酶反应从美得霉素和邻氨基苯甲酸分离出一种新化合物 mederpyrrole A。美德霉素可在温和条件下与伯胺反应,生成具有萘醌-吡咯骨架的嵌合产物。它还可以与蛋白质共价结合。