Details
| Original language | English |
|---|---|
| Pages (from-to) | 12419-12422 |
| Number of pages | 4 |
| Journal | Chemical communications |
| Volume | 56 |
| Issue number | 82 |
| Early online date | 16 Sept 2020 |
| Publication status | Published - 21 Oct 2020 |
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.
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Materials Science(all)
- Electronic, Optical and Magnetic Materials
- Materials Science(all)
- Ceramics and Composites
- Chemistry(all)
- General Chemistry
- Materials Science(all)
- Surfaces, Coatings and Films
- Materials Science(all)
- Metals and Alloys
- Materials Science(all)
- Materials Chemistry
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In: Chemical communications, Vol. 56, No. 82, 21.10.2020, p. 12419-12422.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Biosynthesis of oxygenated brasilane terpene glycosides involves a promiscuousN-acetylglucosamine transferase
AU - Feng, Jin
AU - Surup, Frank
AU - Hauser, Maurice
AU - Miller, Anna
AU - Wennrich, Jan-Peer
AU - Stadler, Marc
AU - Cox, Russell J.
AU - Kuhnert, Eric
N1 - Funding Information: This work was funded by the DFG (Deutsche Forschungsge-meinschaft) priority program ‘‘Taxon-Omics: New Approaches for Discovering and Naming Biodiversity’’ (SPP 1991). DFG is also thanked for 600 MHz NMR equipment (INST 187/686-1). JF was funded by the China Scholarship Council (201709110130) and AM was funded by Erasmus+ and the Carnegie Trust. We would also like to thank Klaus-Peter Conrad for the measurement of HRESIMS data, and Christel Kakoschke for the measurement of NMR spectra (HZI, Braunschweig). Dr Daniel Wibberg (CeBiTec, Bielefeld) is acknowledged for assistance in genome annotation.
PY - 2020/10/21
Y1 - 2020/10/21
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85093539481&partnerID=8YFLogxK
U2 - 10.1039/d0cc03950k
DO - 10.1039/d0cc03950k
M3 - Article
VL - 56
SP - 12419
EP - 12422
JO - Chemical communications
JF - Chemical communications
SN - 1359-7345
IS - 82
ER -