Volume 46, Issue 12 p. 1102-1111
Research Article

Conformational properties of the macrocyclic trichothecene mycotoxin verrucarin A in solution

Georgia Fragaki

Georgia Fragaki

NMR Laboratory, Department of Chemistry, University of Crete, Voutes Campus, 71003 Heraklion, Crete, Greece

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Irine Stefanaki

Irine Stefanaki

NMR Laboratory, Department of Chemistry, University of Crete, Voutes Campus, 71003 Heraklion, Crete, Greece

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Photis Dais

Photis Dais

NMR Laboratory, Department of Chemistry, University of Crete, Voutes Campus, 71003 Heraklion, Crete, Greece

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Emmanuel Mikros

Corresponding Author

Emmanuel Mikros

Department of Pharmaceutical Chemistry, School of Pharmacy, University of Athens, Panepistimiopolis, 15771, Zografou, Greece

Department of Pharmaceutical Chemistry, School of Pharmacy, University of Athens, Panepistimiopolis, 15771, Zografou, Greece.===Search for more papers by this author
First published: 15 October 2008
Citations: 6

Abstract

Phase-sensitive nuclear Overhauser enhancement spectroscopy (NOESY) experiments, 3J couplings and computational molecular modeling (MM2* and MMFF force fields) were employed to examine the conformational properties of verrucarin A in chloroform solutions. The MMFF force field calculations resulted in a family of 12 low-energy structures along with their populations, the latter being determined by the NMR analysis of molecular flexibility in solution(NAMFIS) deconvolution analysis. The concluded model was capable of reproducing successfully the experimental NOESY cross-peak volumes and the proton-coupling constants. Among the 12 conformers, the one which was similar to the structure of verrucarin A in the solid state was the predominant accounting for 75% of the total relative population, although other low-energy conformations contributed to a lesser degree in order to explain the experimental data. Copyright © 2008 John Wiley & Sons, Ltd.