| Title | Assigning the stereochemical structures of aurantinin A and B with the assistance of biosynthetic investigations |
| Authors | Wang, Dacheng Li, Pengwei Yan, Jia-Lei Mao, Huijin Liu, Lilu Wang, Min Chen, Meng Ye, Tao Chen, Yihua |
| Affiliation | Chinese Acad Sci, Inst Microbiol, State Key Lab Microbial Resources, Beijing 100101, Peoples R China Univ Chinese Acad Sci, Beijing 100049, Peoples R China Wuyi Univ, Innovat Ctr Marine Biotechnol & Pharmaceut, Sch Biotechnol & Hlth Sci, Jiangmen 529020, Guangdong, Peoples R China Peking Univ, State Key Lab Chem Oncogen, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China |
| Keywords | CONFIGURATION ELUCIDATION |
| Issue Date | Sep-2022 |
| Publisher | ORGANIC CHEMISTRY FRONTIERS |
| Abstract | Aurantinins (ARTs) are a group of antibacterial polyketides featuring a 6/7/8/5-fused tetracyclic ring system and a triene alkyl chain with a carboxylic terminus. Previous studies assigned their planar structures and proposed ART B as 17-O-glycosylated ART A with a rare 3-keto sugar. In this work, the stereochemical structures of ARTs A and B were assigned by combining the spectroscopic and computational methods with biosynthetic studies. Biosynthetic investigations aided in the assignment of ART A's absolute configuration and provided critical evidence for determining the configuration of ART B's 3-ketosugar moiety, demonstrating that appropriate biosynthetic investigations can be very useful in resolving the complicated structures of certain natural products. |
| URI | http://hdl.handle.net/20.500.11897/654950 |
| ISSN | 2052-4129 |
| DOI | 10.1039/d2qo01251k |
| Indexed | SCI(E) |
| Appears in Collections: | 深圳研究生院待认领 |
