Go, Eun Bin and Kim, Lee Joon and Nelson, Hosea M. and Ohashi, Masao and Tang, Yi (2021) Biosynthesis of the Fusarium Mycotoxin (−)-Sambutoxin. Organic Letters, 23 (20). pp. 7819-7823. ISSN 1523-7060. PMCID PMC8719357. doi:10.1021/acs.orglett.1c02836. https://resolver.caltech.edu/CaltechAUTHORS:20211008-224621528
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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.
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| 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. | ||||||||||||
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| Subject Keywords: | Peptides and proteins, Metabolism, Monomers, Biosynthesis, Fungi | ||||||||||||
| Issue or Number: | 20 | ||||||||||||
| PubMed Central ID: | PMC8719357 | ||||||||||||
| DOI: | 10.1021/acs.orglett.1c02836 | ||||||||||||
| Record Number: | CaltechAUTHORS:20211008-224621528 | ||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20211008-224621528 | ||||||||||||
| Official Citation: | Biosynthesis of the Fusarium Mycotoxin (−)-Sambutoxin. Eun Bin Go, Lee Joon Kim, Hosea M. Nelson, Masao Ohashi, and Yi Tang. Organic Letters 2021 23 (20), 7819-7823; DOI: 10.1021/acs.orglett.1c02836 | ||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||
| ID Code: | 111323 | ||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||
| Deposited By: | George Porter | ||||||||||||
| Deposited On: | 12 Oct 2021 14:36 | ||||||||||||
| Last Modified: | 19 Apr 2022 17:37 |
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