期刊
NATURE
卷 547, 期 7664, 页码 436-440出版社
NATURE PORTFOLIO
DOI: 10.1038/nature23265
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资金
- UK Engineering and Physical Sciences Research Council (EPSRC) [EP/I038071/1]
- European Research Council (ERC) [670668]
- UK Biotechnology and Biological Sciences Research Council (BBSRC)/EPSRC [L01386X]
- Shanghai Institute of Organic Chemistry
- EPSRC Bristol Chemical Synthesis Doctoral Training Centre [EP/L015366/1]
- Biotechnology and Biological Sciences Research Council [BB/L01386X/1] Funding Source: researchfish
- Engineering and Physical Sciences Research Council [1652562, EP/I038071/1, EP/L011999/1] Funding Source: researchfish
- BBSRC [BB/L01386X/1] Funding Source: UKRI
- EPSRC [EP/L011999/1, EP/L015366/1, EP/I038071/1] Funding Source: UKRI
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.
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