Biosynthesis of Valdiazen and Fragin in Burkholderia cenocepacia
Author Information
Author(s): Ren Jiajun, Mathew Anugraha, Rodríguez-García María, Kohler Tobias, Blacque Olivier, Linden Anthony, Eberl Leo, Sieber Simon, Gademann Karl
Primary Institution: University of Zurich
Hypothesis
The ham gene cluster in Burkholderia cenocepacia H111 produces both enantiomerically pure (R)-fragin and racemic valdiazen from a common biosynthetic pathway involving dihydrosydnone N-oxide.
Conclusion
The study reveals a novel mechanism of stereodivergence in the biosynthesis of valdiazen and fragin, highlighting the role of dihydrosydnone N-oxide as a key intermediate.
Supporting Evidence
- The ham gene cluster produces both (R)-fragin and racemic valdiazen.
- Dihydrosydnone N-oxide is identified as a crucial intermediate in the biosynthetic pathway.
- Both non-enzymatic racemization and enzyme-mediated dynamic kinetic resolution are involved in the process.
- Feeding experiments confirmed the production of (R)-fragin from the dihydrosydnone N-oxide intermediate.
Takeaway
This research shows how a single gene cluster in bacteria can create two different types of molecules that are important for communication, using a special intermediate.
Methodology
The study utilized gene knockout, stable isotope feeding experiments, and mass spectrometry to investigate the biosynthetic pathway.
Digital Object Identifier (DOI)
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