Biosynthesis of oxygenated brasilane terpene glycosides involves a promiscuous N-acetylglucosamine transferase.
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Authors
Feng, JinSurup, Frank
Hauser, Maurice
Miller, Anna
Wennrich, Jan-Peer
Stadler, Marc

Cox, Russell J
Kuhnert, Eric
Issue Date
2020-09-16
Metadata
Show full item recordAbstract
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.Citation
Chem Commun (Camb). 2020 Oct 21;56(82):12419-12422. doi: 10.1039/d0cc03950k.Affiliation
HZI,Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7,38124 Braunschweig, Germany.Publisher
Royal Sciety of ChemistryPubMed ID
32936132Type
ArticleLanguage
enEISSN
1364-548Xae974a485f413a2113503eed53cd6c53
10.1039/d0cc03950k
Scopus Count
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- Creative Commons
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