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Gewählte Publikation:

Fruhmann, P; Weigl-Pollack, T; Mikula, H; Wiesenberger, G; Adam, G; Varga, E; Berthiller, F; Krska, R; Hametner, C; Frohlich, J.
(2014): Methylthiodeoxynivalenol (MTD): insight into the chemistry, structure and toxicity of thia-Michael adducts of trichothecenes
ORG BIOMOL CHEM. 2014; 12(28): 5144-5150. FullText FullText_BOKU

Abstract:
Methylthiodeoxynivalenol (MTD), a novel derivative of the trichothecene mycotoxin deoxynivalenol (DON), was prepared by applying a reliable procedure for the formal Michael addition of methanethiol to the conjugated double bond of DON. Structure elucidation revealed the preferred formation of the hemiketal form of MTD by intramolecular cyclisation between C8 and C15. Computational investigations showed a negative total reaction energy for the hemiketalisation step and its decrease in comparison with theoretical model compounds. Therefore, this structural behaviour seems to be a general characteristic of thia-Michael adducts of type B trichothecenes. MTD was shown to be less inhibitory for a reticulocyte lysate based in vitro translation system than the parent compound DON, which supports the
Autor*innen der BOKU Wien:
Adam Gerhard
Berthiller Franz
Krska Rudolf
Varga Elisabeth
Wiesenberger Gerlinde
BOKU Gendermonitor:

Find related publications in this database (using NML MeSH Indexing)
Animals
Biotransformation
Cell-Free System
Cyclization
Genes, Reporter
Luciferases/genetics
Luciferases/metabolism
Mycotoxins/chemical synthesis*
Mycotoxins/metabolism
Mycotoxins/toxicity*
Protein Biosynthesis/drug effects
Rabbits
Reticulocytes/cytology
Reticulocytes/drug effects
Reticulocytes/metabolism*
Sulfhydryl Compounds/chemistry
Thermodynamics
Trichothecenes/chemical synthesis*
Trichothecenes/chemistry
Trichothecenes/metabolism
Trichothecenes/toxicity*



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