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Gewählte Publikation:

Fruhmann, P; Hametner, C; Mikula, H; Adam, G; Krska, R; Frohlich, J.
(2014): Stereoselective Luche Reduction of Deoxynivalenol and Three of Its Acetylated Derivatives at C8
TOXINS. 2014; 6(1): 325-336. FullText FullText_BOKU

Abstract:
The trichothecene mycotoxin deoxynivalenol (DON) is a well known and common contaminant in food and feed. Acetylated derivatives and other biosynthetic precursors can occur together with the main toxin. A key biosynthetic step towards DON involves an oxidation of the 8-OH group of 7,8-dihydroxycalonectrin. Since analytical standards for the intermediates are not available and these intermediates are therefore rarely studied, we aimed for a synthetic method to invert this reaction, making a series of calonectrin-derived precursors accessible. We did this by developing an efficient protocol for stereoselective Luche reduction at C8. This method was used to access 3,7,8,15-tetrahydroxyscirpene, 3-deacetyl-7,8-dihydroxycalonectrin, 15-deacetyl-7,8-dihydroxycalonectrin and 7,8-dihydroxycalonectrin, which were characterized using several NMR techniques. Beside the development of a method which could basically be used for all type B trichothecenes, we opened a synthetic route towards different acetylated calonectrins.
Autor*innen der BOKU Wien:
Adam Gerhard
Krska Rudolf
BOKU Gendermonitor:

Find related publications in this database (using NML MeSH Indexing)
Acetylation;Chromatography, Thin Layer;Magnetic Resonance Spectroscopy;Structure-Activity Relationship;Trichothecenes/chemical synthesis*;Trichothecenes/chemistry*;

Find related publications in this database (Keywords)
dihydroxycalonectrins
trichothecenes
DON
Luche reduction
scirpene


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