Mass spectrometric identification of intermediates in the biosynthesis of cyanogenic glucosides [Sorghum bicolor, gas liquid chromatography-mass spectrometry, trimethylsilylation, amino acids, N-hydroxyamino acids, aldoximes, ketoximes, nitriles, aldehydes]
1979
Moeller, B.L. (Carlsberg Lab., Copenhagen (Denmark). Dept. of Physiology) | Conn, E.E. | Sweeley, C.C.
Mass spectra of trimethylsilyl derivatives of the following compounds, which are related to the biosynthesis of the cyanogenic glucoside dhurrin, are described: tyrosine, N-hydroxytyrosine, p-hydroxyphenylacetaldoxime, p-hydroxyphenylacetonitrile, p-hydroxybenzaldehyde, tyramine, p-hydroxyphenylpyruvic acid oxime, and p-hydroxyphenylpyruvic acid. Accurate mass measurements and metastable transitions support the proposed fragmentation mechanisms. Based on the mass spectrometry data presented, a method is described by which compounds possibly involved as intermediates in the biosynthesis of cyanogenic glucosides can be identified in biosynthetic reaction mixtures.
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