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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
2020-02-05
Source PublicationJOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN0002-7863
Volume142Issue:5Pages:2301-2309
Corresponding AuthorLei, Xinxiang(xxlei@mail.scuec.edu.cn) ; Wang, Bin-Gui(wangbg@ms.qdio.ac.cn) ; Sun, Han(hsun@fmp-berlin.de)
AbstractDetermination 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.
DOI10.1021/jacs.9b10961
Indexed BySCI
Language英语
Funding ProjectNational 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 Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000512222700036
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:8[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.qdio.ac.cn/handle/337002/165323
Collection实验海洋生物学重点实验室
Corresponding AuthorLei, Xinxiang; Wang, Bin-Gui; Sun, Han
Affiliation1.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
Corresponding Author AffilicationKey Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences;  Center for Ocean Mega-Science, Chinese Academy of Sciences
Recommended Citation
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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