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Biosynthesis of the Fusarium Mycotoxin (−)-Sambutoxin

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. 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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acs.orglett.1c02836DOIArticle
https://www.ccdc.cam.ac.uk/services/structure_request?pid=ccdc:2097629&issn=1523-7060&id=doi:10.1021/acs.orglett.1c02836&sid=ACSRelated ItemSupplementary Crystallographic Data
ORCID:
AuthorORCID
Kim, Lee Joon0000-0002-0786-7614
Nelson, Hosea M.0000-0002-4666-2793
Ohashi, Masao0000-0001-7103-541X
Tang, Yi0000-0003-1597-0141
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.
Funders:
Funding AgencyGrant Number
NIH1R01AI141481
NSF Graduate Research FellowshipUNSPECIFIED
Subject Keywords:Peptides and proteins, Metabolism, Monomers, Biosynthesis, Fungi
Issue or Number:20
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:26 Oct 2021 21:53

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