The use of residual dipolar coupling for conformational analysis of structurally related natural products

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Abstract

Determining the conformational preferences of molecules in solution remains a considerable challenge. Recently, the use of residual dipolar coupling (RDC) analysis has emerged as a key method to address this. Whilst to date the majority of the applications have focused on biomolecules including proteins and DNA, the use of RDCs for studying small molecules is gaining popularity. Having said that, the method continues to develop and here we describe an early case study of the quantification of conformer populations in small molecules using RDC analysis. Having been inspired to study conformational preferences by unexpected differences in the NMR spectra and the reactivity of related natural products, we showed that the use of more established techniques was unsatisfactory in explaining the experimental observations. The use of RDCs provided an improved understanding which, following use of methods to quantify conformer populations using RDCs, culminated in a rationalisation of the contrasting diastereoselectivities observed in a ketone reduction reaction
Original languageEnglish
Pages (from-to)467-475
JournalMagnetic Resonance in Chemistry
Volume53
Issue number6
Early online date9 Apr 2015
DOIs
Publication statusPublished - Jun 2015

Keywords

  • NMR
  • 1H
  • 13C
  • Residual dipolar couplings
  • Natural products
  • Solution conformations
  • Conformational analysis
  • Melohenine

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