Conformational analysis of trichothecene mycotoxins : a solution- and solid-state nuclear magnetic resonance (NMR) study

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Shank, Roxanne Angela
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Lethbridge, Alta. : University of Lethbridge, Dept. of Chemistry and Biochemistry
Trichothecenes comprise a large family of sesquiterpenoidal mycotoxins that largely effect the production of cereal crops. Recent advances in structural determination through solution- and solid-state NMR provide new avenues to the understanding of the structural dynamics of these toxins. Refinement of the proton and carbon assignments in deuterated chloroform (CDCl3) are presented for the type A trichothecene T-2 toxin, and the type B trichothecenes deoxynivalenol (DON), nivalenol (NIV), 3-O-acetyldeoxynivalenol (3-ADON), and 15-O-acetyldeoxynivalenol (15-ADON). The effect of different solvent systems on the type B trichothecenes is investigated, and evidence for structural isomerism of the trichothecenes is presented. The mechanism for the rearrangement between the two isomers is presented. Solid-state NMR investigations demonstrate multiple configurations for T-2 toxin, and structural isomerism is shown to exist in the sold-state for DON. Solution- and solid-state NMR data was used to determine the interaction of water with selected trichothecenes, and the water-binding interactions are described.
Trichothecene , NMR , Magnetic Resonance , Solid-State NMR , Toxin , Mycotoxin , Agriculture , Fusarium Head Blight , Deoxynivalenol , T2 Toxin , Nivalenol , Ribosome