Genome Mining from Agriculturally Relevant Fungi Led to a D-Glucose Esterified Polyketide with a Terpene-like Core Structure
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1.
California Institute of Technology
Abstract
Comparison of biosynthetic gene clusters (BGCs) found in devastating plant pathogens and biocontrol fungi revealed an uncharacterized and conserved polyketide BGC. Genome mining identified the associated metabolite to be treconorin, which has a terpene-like, trans-fused 5,7-bicyclic core that is proposed to derive from a (4 + 3) cycloaddition. The core is esterified with d-glucose, which derives from the glycosidic cleavage of a trehalose ester precursor. This glycomodification strategy is different from the commonly observed glycosylation of natural products.
Copyright and License
© 2023 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0.
Acknowledgement
This work was supported by NIFA 2021-67013-34259 (Y.T.) and the HHMI EPI Initiative (Y.T. and H.N.). Chemical characterization studies were supported by shared instrumentation grants from the NSF (CHE-1048804) and the NIH NCRR (S10RR025631). C.Y. was supported by NIGMS predoctoral fellowship 5T32GM136614-04. K.N.H. acknowledges the Saul Winstein Chair in Organic Chemistry for funding. Calculations were performed at Expanse at SDSC through Allocation CHE040014 from the Advanced Cyberinfrastructure Coordination Ecosystem: Services & Support (ACCESS) Program, which is supported by National Science Foundation Grants 2138259, 2138286, 2138307, 2137603, and 2138296.
Conflict of Interest
The authors declare no competing financial interest.
Additional Information
CCDC 2295175 contains the supplementary crystallographic data for this paper.
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Additional details
- ISSN
- 1520-5126
- PMCID
- PMC10682982
- 2021-67013-34259
- National Institute of Food and Agriculture
- Howard Hughes Medical Institute
- CHE-1048804
- National Science Foundation
- S10RR025631
- National Institutes of Health
- NIH Predoctoral Fellowship 5T32GM136614-04
- National Institutes of Health
- Saul Winstein Chair in Organic Chemistry
- University of California, Los Angeles
- CHE040014
- National Science Foundation
- OAC-2138259
- National Science Foundation
- OAC-2138286
- National Science Foundation
- OAC-2138307
- National Science Foundation
- OAC-2137603
- National Science Foundation
- OAC-2138296
- National Science Foundation