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Digital NMR Profiles as Building Blocks: Assembling 1H Fingerprints of Steviol Glycosides
- Napolitano, José G., Simmler, Charlotte, McAlpine, James B., Lankin, David
C., Chen, Shao-Nong, Pauli, Guido F.
- Journal of natural products 2015 v.78 no.4 pp. 658-665
- chemical elements, data collection, glycosides, nuclear magnetic resonance spectroscopy, steviol
- This report describes a fragment-based approach to the examination of congeneric organic compounds by NMR spectroscopy. The method combines the classic interpretation of 1D- and 2D-NMR data sets with contemporary computer-assisted NMR analysis. Characteristic NMR profiles of key structural motifs were generated by ¹H iterative full spin analysis and then joined together as building blocks to recreate the ¹H NMR spectra of increasingly complex molecules. To illustrate the methodology described, a comprehensive analysis of steviol (1), seven steviol glycosides (2–8) and two structurally related isosteviol compounds (9, 10) was carried out. The study also assessed the potential impact of this method on relevant aspects of natural product research including structural verification, chemical dereplication, and mixture analysis.