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Cross-chemistry leads to product diversity from atromentin synthetases in Aspergilli from section Nigri

Geib, Elena; Baldeweg, Florian; Doerfer, Maximilian; Nett, Markus; Brock, Matthias

Authors

Elena Geib

Florian Baldeweg

Maximilian Doerfer

Markus Nett



Abstract

Nonribosomal peptide synthetase (NRPS)-like enzymes catalyse the non-oxidative homodimerisation of aromatic α-keto acids, but the exact reaction mechanism is unknown. The furanone-forming thioesterase domain of the Aspergillus terreus aspulvinone E synthetase MelA displays a predicted quinone-forming motif, whereby its catalytic triad contains an essential cysteine indicating an unusual thioester intermediate. To convert MelA into a quinone-forming atromentin synthetase its thioesterase domain was replaced with that from a Paxillus involutus or A. terreus atromentin synthetase. Phylogenetic proximity of donor and acceptor seems important as only replacement with the A. terreus thioesterase was functional. Heterologous expression of atromentin synthetases in Aspergillus niger and Aspergillus oryzae revealed host-dependent product formation whereby cross-chemistry directed atromentin biosynthesis in A. niger towards atrofuranic acid. Screening of aspergilli from section Nigri identified an atromentin synthetase in Aspergillus brasiliensis that produced atrofuranic acid in the homologous host. Therefore, cross-chemistry on quinone cores appears common to section Nigri.

Journal Article Type Article
Publication Date Feb 21, 2019
Journal Cell Chemical Biology
Electronic ISSN 2451-9456
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 26
Issue 2
Pages 223-234.e6
APA6 Citation Geib, E., Baldeweg, F., Doerfer, M., Nett, M., & Brock, M. (2019). Cross-chemistry leads to product diversity from atromentin synthetases in Aspergilli from section Nigri. Cell Chemical Biology, 26(2), 223-234.e6. https://doi.org/10.1016/j.chembiol.2018.10.021
DOI https://doi.org/10.1016/j.chembiol.2018.10.021
Keywords atromentin; aspulvinone E; Aspergillus oryzae; NRPS-like; thioesterase
Publisher URL https://www.sciencedirect.com/science/article/pii/S2451945618303817?via%3Dihub
Additional Information This article is maintained by: Elsevier; Article Title: Cross-Chemistry Leads to Product Diversity from Atromentin Synthetases in Aspergilli from Section Nigri; Journal Title: Cell Chemical Biology; CrossRef DOI link to publisher maintained version: https://doi.org/10.1016/j.chembiol.2018.10.021; Content Type: article; Copyright: © 2018 Elsevier Ltd.

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