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Synergy of synthesis, computation and NMR reveals correct baulamycin structures

Research output: Research - peer-reviewArticle

Original languageEnglish
Pages (from-to)436-440
Number of pages5
Issue number7664
Early online date26 Jul 2017
StatePublished - 26 Jul 2017


Small-molecule, biologically active natural products continue to be our most rewarding source of, and inspiration for, new medicines. 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. 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, 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.

    Structured keywords

  • BrisSynBio
  • BioDesign



  • Full-text PDF (accepted author manuscript)

    Rights statement: This is the author accepted manuscript (AAM). The final published version (version of record) is available online via Springer Nature at Please refer to any applicable terms of use of the publisher.

    Accepted author manuscript, 1 MB, PDF-document


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