Published October 15, 2021
| Accepted Version + Supplemental Material
Journal Article
Open
Biosynthesis of the Fusarium Mycotoxin (−)-Sambutoxin
Chicago
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Abstract
4-Hydroxy-2-pyridone alkaloids have attracted attention for synthetic and biosynthetic studies due to their broad biological activities and structural diversity. Here, we elucidated the pathway and chemical logic of (−)-sambutoxin (1) biosynthesis. In particular, we uncovered the enzymatic origin of the tetrahydropyran moiety and showed that the p-hydroxyphenyl group is installed via a late-stage, P450-catalyzed oxidation of the phenylalanine-derived side chain rather than via a direct incorporation of tyrosine.
Additional Information
© 2021 American Chemical Society. Received: August 24, 2021; Published: September 28, 2021. This work was supported by grants from the NIH (1R01AI141481) to Y.T. We thank Prof. David Williams from Indiana University for his generous sample of (+)-sambutoxin. E.G. was supported by an NSF Graduate Research Fellowship. CCDC 2097629 contains the supplementary crystallographic data for this paper. The authors declare the following competing financial interest(s): Yi Tang is a co-founder and shareholder of Hexagon Biosciences.Attached Files
Accepted Version - nihms-1767228.pdf
Supplemental Material - ol1c02836_si_001.pdf
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ol1c02836_si_001.pdf
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Additional details
- PMCID
- PMC8719357
- Eprint ID
- 111323
- Resolver ID
- CaltechAUTHORS:20211008-224621528
- NIH
- 1R01AI141481
- NSF Graduate Research Fellowship
- Created
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2021-10-12Created from EPrint's datestamp field
- Updated
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2022-04-19Created from EPrint's last_modified field