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Bioorg Med Chem Lett. 2000 Apr 17;10(8):735-9.

High incorporation of L-amino acids to cereulide, an emetic toxin from Bacillus cereus.

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Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya University, Chikusa, Japan.


Cereulide is a principal toxin causing emetic syndrome produced by Bacillus cereus. This paper deals with biosynthetic studies on this unusual cyclic depsipeptide toxin from 13C labeled L-amino acid precursors (Val, Leu, Ala) upon cultivation in synthetic media. The analyses were made at atomic level of the constituent amino- or oxy-acids through NMR and ESI-MS/MS spectroscopic methods on cereulide and its hydrolysate dipeptides. The incorporation of the 13C atom was 95% in each O-Val, O-Leu and L-Val, while 40% in D-Ala of cereulide.

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