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Conformational properties of the macrocyclic trichothecene mycotoxin verrucarin A in solution
Author(s) -
Fragaki Georgia,
Stefanaki Irine,
Dais Photis,
Mikros Emmanuel
Publication year - 2008
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2298
Subject(s) - chemistry , conformational isomerism , two dimensional nuclear magnetic resonance spectroscopy , chloroform , nuclear overhauser effect , population , trichothecene , force field (fiction) , stereochemistry , nuclear magnetic resonance spectroscopy , proton nmr , spectroscopy , computational chemistry , analytical chemistry (journal) , mycotoxin , molecule , organic chemistry , physics , demography , food science , quantum mechanics , artificial intelligence , sociology , computer science
Phase‐sensitive nuclear Overhauser enhancement spectroscopy (NOESY) experiments, 3 J 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.