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

Author： Domínguez Humberto J. Crespín Guillermo D. Santiago-Benítez Adrián J. Gavín José A. Norte Manuel Fernández José J. Hernández Daranas Antonio

Publisher： MDPI

E-ISSN： 1660-3397|12|1|176-192

ISSN： 1660-3397

Source： Marine Drugs, Vol.12, Iss.1, 2014-01, pp. : 176-192

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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.