Biosynthesis of oxygenated brasilane terpene glycosides involves a promiscuous N-acetylglucosamine transferase.

Autor: Feng, Jin, Surup, Frank, Hauser, Maurice, Miller, Anna, Wennrich, Jan-Peer, Stadler, Marc, Cox, Russell J., Kuhnert, Eric
Předmět:
Zdroj: Chemical Communications; 10/21/2020, Vol. 56 Issue 82, p12419-12422, 4p
Abstrakt: 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. [ABSTRACT FROM AUTHOR]
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