Institutional Repository of Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences
| Stereochemical Elucidation of Natural Products from Residual Chemical Shift Anisotropies in a Liquid Crystalline Phase | |
Li, Xiao-Lu5; Chi, Lu-Ping2,4,6 ; Navarro-Vazquez, Armando7; Hwang, Songhwan5; Schmieder, Peter5; Li, Xiao-Ming2,4; Li, Xin2,4; Yang, Sui-Qun2,4; Lei, Xinxiang1; Wang, Bin-Gui2,3,4; Sun, Han5
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| 2020-02-05 | |
| 发表期刊 | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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| ISSN | 0002-7863 |
| 卷号 | 142期号:5页码:2301-2309 |
| 通讯作者 | Lei, Xinxiang(xxlei@mail.scuec.edu.cn) ; Wang, Bin-Gui(wangbg@ms.qdio.ac.cn) ; Sun, Han(hsun@fmp-berlin.de) |
| 摘要 | Determination of the stereochemistry of organic molecules still represents one of the major obstacles in the structure elucidation procedure in drug discovery. Although the application of residual dipolar couplings (RDCs) has revolutionized this field, residual chemical shift anisotropies (RCSAs) which contain valuable structural information for nonprotonated carbons have only been scarcely employed so far. In this study, we present a simple but highly effective solution to extract RCSAs of the analytes in a liquid crystalline phase formed by AAKLVFF oligopeptides. This method does not require any special instruments, devices, or correction during postacquisition data analysis and thus can be easily applied in any chemistry laboratory. To illustrate the potential of this method, the relative configurations of four known natural products (1-4) belonging to different structural classes were confirmed. Moreover, we unambiguously elucidated the stereochemistry of spiroepicoccin A (5), a rare thiodiketopiperazine marine natural product whose configuration could not be assigned based on conventional NMR methods. |
| DOI | 10.1021/jacs.9b10961 |
| 收录类别 | SCI |
| 语种 | 英语 |
| 资助项目 | National Key R&D Program of China[2018YFC0310800] ; LeibnizForschungsinstitut fur Molekulare Pharmakologie (FMP) ; Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) under DFG/CAPES Collaborative Research Initiative[418729698] ; Germany's Excellence Strategy[EXC 2008/1-390540038] ; Sino-German Center for Research Promotion[GZ1289] ; National Natural Science Foundation of China[21874158] ; National Natural Science Foundation of China[81673351] ; Chinese Scholarship Council ; Research, Vessel KEXUE of the National Major Science and Technology Infrastructure from the Chinese Academy of Sciences[KEXUE2018G28] ; Taishan Scholar Project from Shandong Province |
| WOS研究方向 | Chemistry |
| WOS类目 | Chemistry, Multidisciplinary |
| WOS记录号 | WOS:000512222700036 |
| 出版者 | AMER CHEMICAL SOC |
| 引用统计 | |
| 文献类型 | 期刊论文 |
| 条目标识符 | http://ir.qdio.ac.cn/handle/337002/165323 |
| 专题 | 实验海洋生物学重点实验室 |
| 通讯作者 | Lei, Xinxiang; Wang, Bin-Gui; Sun, Han |
| 作者单位 | 1.South Cent Univ Nationalities, Sch Pharmaceut Sci, Wuhan 430074, Peoples R China 2.Chinese Acad Sci, Inst Oceanol, Key Lab Expt Marine Biol, Qingdao 266071, Peoples R China 3.Chinese Acad Sci, Ctr Ocean Megasci, Qingdao 266071, Peoples R China 4.Qingdao Natl Lab Marine Sci & Technol, Lab Marine Biol & Biotechnol, Qingdao 266071, Peoples R China 5.Leibniz Forschungsinst Mol Pharmakol FMP, Sect Struct Biol, D-13125 Berlin, Germany 6.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 7.Univ Fed Pernambuco, Dept Quim Fundamental, BR-50670901 Recife, PE, Brazil |
| 通讯作者单位 | 实验海洋生物学重点实验室; 中国科学院海洋大科学研究中心 |
| 推荐引用方式 GB/T 7714 | Li, Xiao-Lu,Chi, Lu-Ping,Navarro-Vazquez, Armando,et al. Stereochemical Elucidation of Natural Products from Residual Chemical Shift Anisotropies in a Liquid Crystalline Phase[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2020,142(5):2301-2309. |
| APA | Li, Xiao-Lu.,Chi, Lu-Ping.,Navarro-Vazquez, Armando.,Hwang, Songhwan.,Schmieder, Peter.,...&Sun, Han.(2020).Stereochemical Elucidation of Natural Products from Residual Chemical Shift Anisotropies in a Liquid Crystalline Phase.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,142(5),2301-2309. |
| MLA | Li, Xiao-Lu,et al."Stereochemical Elucidation of Natural Products from Residual Chemical Shift Anisotropies in a Liquid Crystalline Phase".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 142.5(2020):2301-2309. |
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