Biosynthesis of the Fusarium Mycotoxin (−)-Sambutoxin

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...

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Veröffentlicht in:Organic letters 2021-10, Vol.23 (20), p.7819-7823
Hauptverfasser: Go, Eun Bin, Kim, Lee Joon, Nelson, Hosea M, Ohashi, Masao, Tang, Yi
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids - chemistry
Fusarium - chemistry
Fusarium - metabolism
Molecular Structure
Mycotoxins - chemistry
Oxidation-Reduction
Phenylalanine - chemistry
Pyridines - chemistry
Tyrosine - chemistry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02836