Biosynthesis of oxygenated brasilane terpene glycosides involves a promiscuous N-acetylglucosamine transferase.
Average rating
Cast your vote
You can rate an item by clicking the amount of stars they wish to award to this item.
When enough users have cast their vote on this item, the average rating will also be shown.
Star rating
Your vote was cast
Thank you for your feedback
Thank you for your feedback
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
The following license files are associated with this item:
- Creative Commons
Except where otherwise noted, this item's license is described as Attribution-NonCommercial-ShareAlike 4.0 International
Related articles
- Generation of complexity in fungal terpene biosynthesis: discovery of a multifunctional cytochrome P450 in the fumagillin pathway.
- Authors: Lin HC, Tsunematsu Y, Dhingra S, Xu W, Fukutomi M, Chooi YH, Cane DE, Calvo AM, Watanabe K, Tang Y
- Issue date: 2014 Mar 19
- Genetic and structural validation of Aspergillus fumigatus UDP-N-acetylglucosamine pyrophosphorylase as an antifungal target.
- Authors: Fang W, Du T, Raimi OG, Hurtado-Guerrero R, Urbaniak MD, Ibrahim AF, Ferguson MA, Jin C, van Aalten DM
- Issue date: 2013 Aug
- Ascomycete Aspergillus oryzae Is an Efficient Expression Host for Production of Basidiomycete Terpenes by Using Genomic DNA Sequences.
- Authors: Nagamine S, Liu C, Nishishita J, Kozaki T, Sogahata K, Sato Y, Minami A, Ozaki T, Schmidt-Dannert C, Maruyama JI, Oikawa H
- Issue date: 2019 Aug 1
- UDP-N-trifluoroacetylglucosamine as an alternative substrate in N-acetylglucosaminyltransferase reactions.
- Authors: Sala RF, MacKinnon SL, Palcic MM, Tanner ME
- Issue date: 1998 Jan
- Novel acetylation-aided migrating rearrangement of uridine-diphosphate-N-acetylglucosamine in electrospray ionization multistage tandem mass spectrometry.
- Authors: Liu HD, Li YM, Du JT, Hu J, Zhao YF
- Issue date: 2006 Feb