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Published on: October 4, 2019
Biosynthesis of oxygenated brasilane terpene glycosides involves a promiscuous N-acetylglucosamine transferase
Jin Feng1, Frank Surup, Maurice Hauser
1Institute for Organic Chemistry and Centre for Biomolecular Drug Research (BMWZ), Leibniz University Hannover, Schneiderberg 38, Hannover 30167, Germany. eric.kuhnert@oci.uni-hannover.de.
Abstract:
Investigation of the metabolome of the ascomycete Annulohypoxylon truncatum led to the identification of novel oxygenated brasilane glycosides and the revision of the stereochemistry of the brasilane A octahydro-1H-indene core scaffold to trans. The bra biosynthetic gene cluster containing five genes (braA-braE) was identified and verified by heterologous expression experiments in Aspergillus oryzae demonstrating that BraC is a multifunctional P450 monooxygenase. In vitro studies of BraB revealed it to be a very rare fungal UDP-GlcNAc dependent N-acetylglucosamine transferase. UDP-glucose is also accepted as a donor, and a broad acceptor substrate tolerance for various primary and secondary alcohols was observed.
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