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Published October 15, 2021 | Accepted Version + Supplemental Material
Journal Article Open

Biosynthesis of the Fusarium Mycotoxin (−)-Sambutoxin


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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August 20, 2023
October 23, 2023