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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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University Institute of Bio-Organic Chemistry "Antonio González" (CIBICAN), Avda. Astrofísico Francisco Sánchez 2, La Laguna 38206, Spain
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Department of Organic Chemistry, Faculty of Pharmacy, Avda. Astrofísico Francisco Sánchez s/n, La Laguna 38206, Spain
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School of Chemistry, Faculty of Natural Science and Mathematics, University El Salvador, Final 25, Avda. Norte, San Salvador, El Salvador
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Department of Chemical Engineering and Pharmaceutical Technology, Faculty of Pharmacy, Avda. Astrofísico Francisco Sánchez s/n, La Laguna 38206, Spain
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Author to whom correspondence should be addressed.
Mar. Drugs 2014, 12(1), 176-192; https://doi.org/10.3390/md12010176
Received: 9 December 2013 / Revised: 19 December 2013 / Accepted: 23 December 2013 / Published: 7 January 2014
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. View Full-Text
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
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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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