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1. (Article ID: 9150)
 
Feng J, Surup F, Hauser M, Miller A, Wennrich JP, Stadler M, Cox RJ, Kuhnert E
Biosynthesis of oxygenated brasilane terpene glycosides involves a promiscuous N-acetylglucosamine transferase
Chemical Communications 56(82) (2020) 12419-12422
 

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.

biosynthesis, P450 monooxygenase, brasilane terpene glycosides, Annulohypoxylon truncatum, N-acetylglucosamine transferase

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