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

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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 (braAbraE) 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.

Graphical abstract: Biosynthesis of oxygenated brasilane terpene glycosides involves a promiscuous N-acetylglucosamine transferase

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Article information


Submitted
05 Jun 2020
Accepted
02 Sep 2020
First published
16 Sep 2020

This article is Open Access

Chem. Commun., 2020, Advance Article
Article type
Communication

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

J. Feng, F. Surup, M. Hauser, A. Miller, J. Wennrich, M. Stadler, R. J. Cox and E. Kuhnert, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC03950K

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