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Mar. Drugs 2014, 12(1), 176-192; doi:10.3390/md12010176
Article

Stereochemistry of Complex Marine Natural Products by Quantum Mechanical Calculations of NMR Chemical Shifts: Solvent and Conformational Effects on Okadaic Acid

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Received: 9 December 2013 / Revised: 19 December 2013 / Accepted: 23 December 2013 / Published: 7 January 2014
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Abstract

Marine organisms are an increasingly important source of novel metabolites, some of which have already inspired or become new drugs. In addition, many of these molecules show a high degree of novelty from a structural and/or pharmacological point of view. Structure determination is generally achieved by the use of a variety of spectroscopic methods, among which NMR (nuclear magnetic resonance) plays a major role and determination of the stereochemical relationships within every new molecule is generally the most challenging part in structural determination. In this communication, we have chosen okadaic acid as a model compound to perform a computational chemistry study to predict 1H and 13C NMR chemical shifts. The effect of two different solvents and conformation on the ability of DFT (density functional theory) calculations to predict the correct stereoisomer has been studied.
Keywords: quantum mechanical calculations; nuclear magnetic resonance; chemical shifts; marine toxin; structure determination; stereochemistry quantum mechanical calculations; nuclear magnetic resonance; chemical shifts; marine toxin; structure determination; stereochemistry
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Domínguez, H.J.; Crespín, G.D.; Santiago-Benítez, A.J.; Gavín, J.A.; Norte, M.; Fernández, J.J.; Daranas, A.H. Stereochemistry of Complex Marine Natural Products by Quantum Mechanical Calculations of NMR Chemical Shifts: Solvent and Conformational Effects on Okadaic Acid. Mar. Drugs 2014, 12, 176-192.

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