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DOI | 10.1038/nature25454 |
Synergy of synthesis, computation and NMR reveals correct baulamycin structures | |
Wu, Jingjing1; Lorenzo, Paula1; Zhong, Siying1; Ali, Muhammad1,2; Butts, Craig P.1; Myers, Eddie L.1; Aggarwal, Varinder K.1 | |
2017-07-27 | |
发表期刊 | NATURE |
ISSN | 0028-0836 |
EISSN | 1476-4687 |
出版年 | 2017 |
卷号 | 547期号:7664页码:436-440 |
文章类型 | Article |
语种 | 英语 |
国家 | England; Pakistan |
英文摘要 | Small-molecule, biologically active natural products continue to be our most rewarding source of, and inspiration for, new medicines(1). Sometimes we happen upon such molecules in minute quantities in unique, difficult-to-reach, and often fleeting environments, perhaps never to be discovered again. In these cases, determining the structure of a molecule-including assigning its relative and absolute configurations-is paramount, enabling one to understand its biological activity. Molecules that comprise stereochemically complex acyclic and conformationally flexible carbon chains make such a task extremely challenging(2). The baulamycins (A and B) serve as a contemporary example. Isolated in small quantities and shown to have promising antimicrobial activity, the structure of the conformationally flexible molecules was determined largely through J-based configurational analysis(3,4), but has been found to be incorrect. Our subsequent campaign to identify the true structures of the baulamycins has revealed a powerful method for the rapid structural elucidation of such molecules. Specifically, the prediction of nuclear magnetic resonance (NMR) parameters through density functional theory-combined with an efficient sequence of boron-based synthetic transformations, which allowed an encoded (labelled) mixture of natural-product diastereomers to be prepared-enabled us rapidly to pinpoint and synthesize the correct structures. |
领域 | 地球科学 ; 气候变化 ; 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000406358300032 |
WOS关键词 | NATURAL-PRODUCTS ; CHEMICAL-SHIFTS ; BORONIC ESTERS ; ALDEHYDES ; ALLYLBORATION ; HYDROBORATION ; ANTIBIOTICS ; MOLECULES ; ALKENES ; H-1 |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
URL | 查看原文 |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/202849 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Univ Bristol, Sch Chem, Cantocks Close, Bristol BS8 1TS, Avon, England; 2.COMSATS Inst Informat Technol, Dept Chem, Abbottabad 22060, Pakistan |
推荐引用方式 GB/T 7714 | Wu, Jingjing,Lorenzo, Paula,Zhong, Siying,et al. Synergy of synthesis, computation and NMR reveals correct baulamycin structures[J]. NATURE,2017,547(7664):436-440. |
APA | Wu, Jingjing.,Lorenzo, Paula.,Zhong, Siying.,Ali, Muhammad.,Butts, Craig P..,...&Aggarwal, Varinder K..(2017).Synergy of synthesis, computation and NMR reveals correct baulamycin structures.NATURE,547(7664),436-440. |
MLA | Wu, Jingjing,et al."Synergy of synthesis, computation and NMR reveals correct baulamycin structures".NATURE 547.7664(2017):436-440. |
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