Complex Polypropionates from a South China Sea Photosynthetic Mollusk: Isolation and Biomimetic Synthesis Highlighting Novel Rearrangements
文献类型：期刊论文
| 作者 | Wu, Qihao4,5; Li, Song-Wei2,4; Xu, Heng4; Wang, Hong5; Hu, Pei4; Zhang, Hao4; Luo, Cheng3,4 ; Chen, Kai-Xian3,4; Nay, Bastien1; Guo, Yue-Wei3,4
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| 刊名 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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| 出版日期 | 2020-05-20 |
| 页码 | 9 |
| 关键词 | biomimetic synthesis biosynthetic rearrangements marine natural products polyketides Sacoglossan mollusk |
| ISSN号 | 1433-7851 |
| DOI | 10.1002/anie.202003643 |
| 通讯作者 | Nay, Bastien(bastien.nay@polytechnique.edu) ; Guo, Yue-Wei(ywguo@simm.ac.cn) ; Li, Xu-Wen(xwli@simm.ac.cn) |
| 英文摘要 | Placobranchus ocellatus is well known to produce diverse and complex gamma-pyrone polypropionates. In this study, the chemical investigation of P. ocellatus from the South China Sea led to the discovery and identification of ocellatusones A-D, a series of racemic non-gamma-pyrone polyketides with novel skeletons, characterized by a bicyclo[3.2.1]octane (1, 2), a bicyclo[3.3.1]nonane (3) or a mesitylene-substituted dimethylfuran-3(2H)-one core (4). Extensive spectroscopic analysis, quantum chemical computation, chemical synthesis, and/or X-ray diffraction analysis were used to determine the structure and absolute configuration of the new compounds, including each enantiomer of racemic compounds 1-4 after chiral HPLC resolution. An array of new and diversity-generating rearrangements is proposed to explain the biosynthesis of these unusual compounds based on careful structural analysis and comparison with six known co-occurring gamma-pyrones (5-10). Furthermore, the successful biomimetic semisynthesis of ocellatusone A (1) confirmed the proposed rearrangement through an unprecedented acid induced cascade reaction. |
| WOS关键词 | MOLECULAR NETWORKING ; CIRCULAR-DICHROISM ; NATURAL-PRODUCTS ; BIOSYNTHESIS ; PATHWAYS ; PYRONES ; METABOLITES ; CHEMISTRY ; REVISION ; 1ST |
| 资助项目 | National Natural Science Foundation of China (NSFC)[81991521] ; National Natural Science Foundation of China (NSFC)[41676073] ; National Natural Science Foundation of China (NSFC)[81520108028] ; National Natural Science Foundation of China (NSFC)[21672230] ; NSFC/CNRS joint project[81811530284] ; National Key Research and Development Program of China[2018YFC0310903] ; Drug Innovation Major Project[2018ZX09711-001-001-009] ; SKLDR/SIMM Project[SIMM1903ZZ-04] ; Chinese Academy of Sciences[2016258] ; SA-SIBS Scholarship Program |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000534072800001 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/280330]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Nay, Bastien; Guo, Yue-Wei; Li, Xu-Wen |
| 作者单位 | 1.Ecole Polytech, Inst Polytech Paris, CNRS, Lab Synth Organ,ENSTA, F-91128 Palaiseau, France 2.Nanjing Univ Chinese Med, 138 Xianlin Rd, Nanjing 210023, Peoples R China 3.Pilot Natl Lab Marine Sci & Technol, Open Studio Druggabil Res Marine Nat Prod, 1 Wenhai Rd, Qingdao 266237, Peoples R China 4.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Chong Zhi Rd,Zhangjiang Hitech Pk, Shanghai 201203, Peoples R China 5.Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Peoples R China |
| 推荐引用方式 GB/T 7714 | Wu, Qihao,Li, Song-Wei,Xu, Heng,et al. Complex Polypropionates from a South China Sea Photosynthetic Mollusk: Isolation and Biomimetic Synthesis Highlighting Novel Rearrangements[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2020:9. |
| APA | Wu, Qihao.,Li, Song-Wei.,Xu, Heng.,Wang, Hong.,Hu, Pei.,...&Li, Xu-Wen.(2020).Complex Polypropionates from a South China Sea Photosynthetic Mollusk: Isolation and Biomimetic Synthesis Highlighting Novel Rearrangements.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,9. |
| MLA | Wu, Qihao,et al."Complex Polypropionates from a South China Sea Photosynthetic Mollusk: Isolation and Biomimetic Synthesis Highlighting Novel Rearrangements".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020):9. |
入库方式： OAI收割
来源：上海药物研究所
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