Synthetic Bioorganic Chemistry
As a research group that emphasizes SYNTHETIC COMPETENCE, we are interested in efficient applications of synthetic methodologies in target-oriented synthesis. Particularly interesting are cooperation projects with biologically oriented groups.
Oxyluciferin - the emitter of firefly bioluminescence
The bioluminescence of fireflies is a fascinating phenomenon that has been studied intensively. Such studies have led to practical applications particularly in the field of bioanalytics.
Oxyluciferin is the emitter (light emitting molecule) of the firefly. It is enzymatically generated in its excited state from luciferin and oxygen.
The compound is reactive and readily decomposes in solution. We have developed reliable syntheses for oxyluciferin and its analogs. We were able to clarify the mechanism of its decomposition. We had to reject previously accepted, 40 years old theories about this substance (e.g., oxygen sensitivity)!
By means of synthetic oxylucferin and its derivatives, we and our cooperation partners were able to perform diverse measurements on this molecule:
• keto-enol equilibrium in solution (Angew. Chem. 2014, 126, 866)
• tripple-equilibrium (pKa1, pKa2, KE) in buffers (Chem. Sci. 2013, 4, 3803
• mass spectrometry (J. Am. Chem. Soc. 2013, 135, 6485; Int. J. Mass Spectrom. 2014, ASAP.)
• IR-spectroscopy with isotope labeled derivatives (Chem. Eur. J. 2014, in print)