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

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Westwood_2015_MRC_TheUse_AM.pdf (717.9Kb)
Date
06/2015
Author
Lancefield, Christopher Stuart
Slawin, Alexandra Martha Zoya
Westwood, Nicholas James
Lebl, Tomas
Keywords
NMR
1H
13C
Residual dipolar couplings
Natural products
Solution conformations
Conformational analysis
Melohenine
QD Chemistry
DAS
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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
Citation
Lancefield , C S , Slawin , A M Z , Westwood , N J & Lebl , T 2015 , ' The use of residual dipolar coupling for conformational analysis of structurally related natural products ' , Magnetic Resonance in Chemistry , vol. 53 , no. 6 , pp. 467-475 . https://doi.org/10.1002/mrc.4213
Publication
Magnetic Resonance in Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1002/mrc.4213
ISSN
0749-1581
Type
Journal article
Rights
Copyright © 2014 John Wiley & Sons, Ltd. This is the accepted version of the following article: Lancefield, C. S., Slawin, A. M. Z., Westwood, N. J. and Lebl, T. (2015), The use of residual dipolar coupling for conformational analysis of structurally related natural products. Magn. Reson. Chem., which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/mrc.4213/abstract
Description
The authors would like to acknowledge the EPSRC for funding.
Collections
  • University of St Andrews Research
URL
http://onlinelibrary.wiley.com/doi/10.1002/mrc.4213/suppinfo
URI
http://hdl.handle.net/10023/8587

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