Accurate prediction of the optical rotation and NMR properties for highly flexible chiral natural products

Despite advances in electronic structure theory the theoretical prediction of spectroscopic properties remains a computational challenge. This is especially true for natural products that exhibit very large conformational freedom and hence need to be sampled over many different accessible conformati...

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Bibliographic Details
Published in:Physical chemistry chemical physics : PCCP 2016-01, Vol.18 (35), p.2456-2451
Main Authors: Hashmi, Muhammad Ali, Andreassend, Sarah K, Keyzers, Robert A, Lein, Matthias
Format: Article
Language:English
Subjects:
Accessibility
Carbon
Mathematical analysis
Natural products
Nuclear magnetic resonance
Optical properties
Optical rotation
Strategy
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Summary:Despite advances in electronic structure theory the theoretical prediction of spectroscopic properties remains a computational challenge. This is especially true for natural products that exhibit very large conformational freedom and hence need to be sampled over many different accessible conformations. We report a strategy, which is able to predict NMR chemical shifts and more elusive properties like the optical rotation with great precision, through step-wise incremental increases of the conformational degrees of freedom. The application of this method is demonstrated for 3- epi -xestoaminol C, a chiral natural compound with a long, linear alkyl chain of 14 carbon atoms. Experimental NMR and [ ] D values are reported to validate the results of the density functional theory calculations. Despite advances in electronic structure theory the theoretical prediction of spectroscopic properties remains a computational challenge.
ISSN:1463-9076
1463-9084
DOI:10.1039/c6cp04828e