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Marine Drugs
Volume 12
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10.3390/md12010176
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Article

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

by
Humberto J. Domínguez
1,2,
Guillermo D. Crespín
1,3,
Adrián J. Santiago-Benítez
1,
José A. Gavín
1,2,
Manuel Norte
1,2,
José J. Fernández
1,2 and
Antonio Hernández Daranas
1,4,*
1
University Institute of Bio-Organic Chemistry "Antonio González" (CIBICAN), Avda. Astrofísico Francisco Sánchez 2, La Laguna 38206, Spain
2
Department of Organic Chemistry, Faculty of Pharmacy, Avda. Astrofísico Francisco Sánchez s/n, La Laguna 38206, Spain
3
School of Chemistry, Faculty of Natural Science and Mathematics, University El Salvador, Final 25, Avda. Norte, San Salvador, El Salvador
4
Department of Chemical Engineering and Pharmaceutical Technology, Faculty of Pharmacy, Avda. Astrofísico Francisco Sánchez s/n, La Laguna 38206, Spain
*
Author to whom correspondence should be addressed.
Mar. Drugs 2014, 12(1), 176-192; https://doi.org/10.3390/md12010176
Submission received: 9 December 2013 / Revised: 19 December 2013 / Accepted: 23 December 2013 / Published: 7 January 2014
(This article belongs to the Special Issue Selected Papers from the 14th International Symposium on Marine Natural Products)
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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
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MDPI and ACS Style

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. https://doi.org/10.3390/md12010176

AMA Style

Domínguez HJ, Crespín GD, Santiago-Benítez AJ, Gavín JA, Norte M, Fernández JJ, Daranas AH. Stereochemistry of Complex Marine Natural Products by Quantum Mechanical Calculations of NMR Chemical Shifts: Solvent and Conformational Effects on Okadaic Acid. Marine Drugs. 2014; 12(1):176-192. https://doi.org/10.3390/md12010176

Chicago/Turabian Style

Domínguez, Humberto J., Guillermo D. Crespín, Adrián J. Santiago-Benítez, José A. Gavín, Manuel Norte, José J. Fernández, and Antonio Hernández Daranas. 2014. "Stereochemistry of Complex Marine Natural Products by Quantum Mechanical Calculations of NMR Chemical Shifts: Solvent and Conformational Effects on Okadaic Acid" Marine Drugs 12, no. 1: 176-192. https://doi.org/10.3390/md12010176

APA Style

Domínguez, H. J., Crespín, G. D., Santiago-Benítez, A. J., Gavín, J. A., Norte, M., Fernández, J. J., & Daranas, A. H. (2014). Stereochemistry of Complex Marine Natural Products by Quantum Mechanical Calculations of NMR Chemical Shifts: Solvent and Conformational Effects on Okadaic Acid. Marine Drugs, 12(1), 176-192. https://doi.org/10.3390/md12010176

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