Biosynthesis of oxygenated brasilane terpene glycosides involves a promiscuous N-acetylglucosamine transferase
| Autor: | Jin Feng, Eric Kuhnert, Jan-Peer Wennrich, Anna Miller, Maurice Hauser, Frank Surup, Marc Stadler, Russell J. Cox |
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| Přispěvatelé: | HZI,Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7,38124 Braunschweig, Germany. |
| Rok vydání: | 2020 |
| Předmět: |
Dewey Decimal Classification::500 | Naturwissenschaften::540 | Chemie
Annulohypoxylon truncatum Aspergillus oryzae 010402 general chemistry N-Acetylglucosaminyltransferases 01 natural sciences Catalysis Substrate Specificity chemistry.chemical_compound Biosynthesis Ascomycota Cytochrome P-450 Enzyme System Gene cluster Materials Chemistry N-Acetylglucosamine Metabolome Transferase Glycosides monooxygenase chemistry.chemical_classification biosynthetic gene cluster biology 010405 organic chemistry Terpenes Metals and Alloys Glycoside Stereoisomerism General Chemistry biology.organism_classification 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials Oxygen chemistry Biochemistry Multigene Family ddc:540 Ceramics and Composites Heterologous expression Sesquiterpenes |
| Zdroj: | Chemical communications (Cambridge, England) England Chemical Communications 56 (2020), Nr. 82 Chemical Communications |
| ISSN: | 1364-548X |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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