Discovery of a Phenylamine-Incorporated Angucyclinone from Marine Streptomyces sp. PKU-MA00218 and Generation of Derivatives with Phenylamine Analogues
| Autor: | Guiyang Wang, Jing Jin, Tan Liu, Tongtong Geng, Youming Zhang, Baiying Xing, Hailong Wang, Zhongyi Zhang, Xiaoyan Yang, Juan Song, Hua Xiao, Yuanjie Ge, Xiaoxu Sun, Changbiao Chi, Jiahui Yu, Ming Ma, Yi Kuang, Xiaojie Ma, Donghui Yang, Xueyang Ma, Min Ye |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Aquatic Organisms
Aniline Compounds biology 010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Structural diversity Anthraquinones 010402 general chemistry biology.organism_classification 01 natural sciences Biochemistry Streptomyces Biosynthetic Pathways 0104 chemical sciences Angucyclinone Structure-Activity Relationship Polyketides Fermentation Moiety Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 21:2813-2817 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.9b00800 |
| Popis: | A new phenylamine-incorporated angucyclinone (1) featuring a unique 1-phenylbenzo[ cd]indol-3(1 H)-one moiety was discovered from marine Streptomyces sp. PKU-MA00218. A series of experimental investigations identified that 1 was produced from the nonenzymatic conversion of a C-ring-cleaved angucyclinone (2) with phenylamine. Utilizing the nonenzymatic conversion, 18 phenylamine-incorporated angucyclinone derivatives with halogen, methyl, methoxy, and carboxy substitutions were efficiently generated under mild conditions. These results highlighted the impressive roles of nonenzymatic reactions in expanding the structural diversity of angucyclinones. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|