High incorporation of L-amino acids to cereulide, an emetic toxin from Bacillus cereus.
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.
Kuse
M
M
Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya University, Chikusa, Japan.
Franz
T
T
Koga
K
K
Suwan
S
S
Isobe
M
M
Agata
N
N
Ohta
M
M
D000596:Amino Acids / Q000737:chemistry*; D001412:Bacillus subtilis / Q000737:chemistry*; D001427:Bacterial Toxins / Q000737:chemistry*; D047630:Depsipeptides; D013058:Mass Spectrometry; D010456:Peptides, Cyclic / Q000737:chemistry*
D000596:Amino Acids; D001427:Bacterial Toxins; D047630:Depsipeptides; D010456:Peptides, Cyclic; C089294:cereulide