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(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](/fileadmin/_processed_/7/5/csm_chart_synthesis_1_800px_e20babcdc3.webp)
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.](/fileadmin/_processed_/8/d/csm_chart_synthesis_2_800px_02_e1f2e0869e.webp)