Computer‐Assisted 3D Structure Elucidation of Natural Products using Residual Dipolar Couplings

An enhanced computer‐assisted procedure for the determination of the relative configuration of natural products, which starts from the molecular formula and uses a combination of conventional 1D and 2D NMR spectra, and residual dipolar couplings (RDCs), is reported. Having already the data acquired...

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Bibliographic Details
Published in:Angewandte Chemie 2017-03, Vol.129 (13), p.3714-3718
Main Authors: Troche‐Pesqueira, Eduardo, Anklin, Clemens, Gil, Roberto R., Navarro‐Vázquez, Armando
Format: Article
Language:eng ; ger
Subjects:
Chemistry
Constitution
Coupling (molecular)
Couplings
Criteria
Data acquisition
Dipolare Restkopplungen
Kleine Moleküle
Molecular structure
Natural products
NMR
NMR-Spektroskopie
Nuclear magnetic resonance
Spectra
Stereochemie
Strukturaufklärung
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Summary:An enhanced computer‐assisted procedure for the determination of the relative configuration of natural products, which starts from the molecular formula and uses a combination of conventional 1D and 2D NMR spectra, and residual dipolar couplings (RDCs), is reported. Having already the data acquired (1D/2D NMR and RDCs), the procedure begins with the determination of the molecular constitution using standard computer‐assisted structure elucidation (CASE) and is followed by fully automated determination of relative configuration through RDC analysis. In the case of moderately flexible molecules the simplest data‐explaining conformational model is selected by the use of the Akaike information criterion. Beweis durch Kopplung: Die Relativkonfiguration von Naturstoffen kann durch eine Kombination gängiger 1D‐ und 2D‐NMR‐Spektren mit dipolaren Restkopplungen (RDCs) ausgehend von der Summenformel bestimmt werden. Dabei wird zuerst die Molekülkonstitution über standardmäßige computergestützte Strukturaufklärung (CASE) festgelegt und anschließend in einer RDC‐Analyse die Relativkonfiguration ermittelt.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201612454