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

Marine Drugs

Humberto J. Domínguez¹  Guillermo D. Crespín¹  Adrián J. Santiago-Benítez¹  José A. Gavín¹  Manuel Norte¹  José J. Fernández¹ 

[1] University Institute of Bio-Organic Chemistry “Antonio González” (CIBICAN), Avda. Astrofísico Francisco Sánchez 2, La Laguna 38206, Spain; E-Mails:

关键词: quantum mechanical calculations;    nuclear magnetic resonance;    chemical shifts;    marine toxin;    structure determination;    stereochemistry;   

DOI  :  10.3390/md12010176

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.