(Bio)organic Synthesis

Organic synthesis of reference compounds is performed (i) to unequivocally confirm the chemical structure and stereochemistry of a previously not reported natural product, (ii) to perform bioactivity studies with suitable amounts of a target molecule, and (iii) to perform accurate quantitative analyses using stable isotope labeled twin molecules of the target analytes as internal standards.

Stereoselective synthesis of the stereoisomers of the bitter-tasting phytoallexin falcarindiol: (3R,8S)-, (3R,8R)-, (3S, 8S)-, and (3S,8S)-falcarindiol

If suitable, target compounds are synthesized by using the metabolic power of microorganisms fed with suitable precursor molecules. For the first time, this biosynthetic approach successfully allowed the synthesis of a 13C-labelled twin molecule of cereulide, the emetic toxin of Bacillus cereus, and enabled the development of a stable isotope dilution analysis.

Biosynthetic production of 13C-cereulide by growing B. cereus in MOD medium with the 13C-labelled precursor amino acid valine.