Multiple Oxidative Modifications in the Ophiobolin Biosynthesis: P450 Oxidations Found in Genome Mining

Koji Narita; Ryota Chiba; Atsushi Minami; Motoichiro Kodama; Isao Fujii; Katsuya Gomi; Hideaki Oikawa

doi:10.1021/acs.orglett.6b00552

Multiple Oxidative Modifications in the Ophiobolin Biosynthesis: P450 Oxidations Found in Genome Mining

Koji Narita, Ryota Chiba, Atsushi Minami, Motoichiro Kodama, Isao Fujii, Katsuya Gomi, Hideaki Oikawa

Research output: Contribution to journal › Article › peer-review

21 Citations (Scopus)

Abstract

Heterologous expression of four candidate genes found in ophiobolin gene clusters from three fungal strains was employed to elucidate the late-stage biosynthetic pathway of phytotoxin ophiobolin. Expression of oblB_Ac (cytochrome P450) from the cryptic gene cluster gave unexpected products, and that of oblB_Bm/oblB_Ev from the gene cluster of ophiobolin producers, with oblD_Bm as the transporter, yielded intermediate ophiobolin C through an unusual four-step oxidation process. The observation made in this study may provide a useful guideline for the elucidation of genuine biosynthetic pathways of natural products.

Original language	English
Pages (from-to)	1980-1983
Number of pages	4
Journal	Organic letters
Volume	18
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.6b00552
Publication status	Published - 2016 May 6
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.6b00552

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title = "Multiple Oxidative Modifications in the Ophiobolin Biosynthesis: P450 Oxidations Found in Genome Mining",

abstract = "Heterologous expression of four candidate genes found in ophiobolin gene clusters from three fungal strains was employed to elucidate the late-stage biosynthetic pathway of phytotoxin ophiobolin. Expression of oblBAc (cytochrome P450) from the cryptic gene cluster gave unexpected products, and that of oblBBm/oblBEv from the gene cluster of ophiobolin producers, with oblDBm as the transporter, yielded intermediate ophiobolin C through an unusual four-step oxidation process. The observation made in this study may provide a useful guideline for the elucidation of genuine biosynthetic pathways of natural products.",

author = "Koji Narita and Ryota Chiba and Atsushi Minami and Motoichiro Kodama and Isao Fujii and Katsuya Gomi and Hideaki Oikawa",

note = "Funding Information: This work was financially supported by a MEXT research grant for Scientific Research (A) (15H01835) and partly by a grant for Challenging Exploratory Research (15K12737) to H.O. We are grateful to Dr. J. Ishikawa (National Institute of Infectious Diseases) for genomic analysis of E. variecolor GF10 and Profs. S. Kobayashi (Osaka University) and J. Turgeon (Cornell University) for samples of E. variecolor GF10 and B. maydes C5, respectively. Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

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doi = "10.1021/acs.orglett.6b00552",

language = "English",

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T2 - P450 Oxidations Found in Genome Mining

AU - Narita, Koji

AU - Chiba, Ryota

AU - Minami, Atsushi

AU - Kodama, Motoichiro

AU - Fujii, Isao

AU - Gomi, Katsuya

AU - Oikawa, Hideaki

N1 - Funding Information: This work was financially supported by a MEXT research grant for Scientific Research (A) (15H01835) and partly by a grant for Challenging Exploratory Research (15K12737) to H.O. We are grateful to Dr. J. Ishikawa (National Institute of Infectious Diseases) for genomic analysis of E. variecolor GF10 and Profs. S. Kobayashi (Osaka University) and J. Turgeon (Cornell University) for samples of E. variecolor GF10 and B. maydes C5, respectively. Publisher Copyright: © 2016 American Chemical Society.

PY - 2016/5/6

Y1 - 2016/5/6

N2 - Heterologous expression of four candidate genes found in ophiobolin gene clusters from three fungal strains was employed to elucidate the late-stage biosynthetic pathway of phytotoxin ophiobolin. Expression of oblBAc (cytochrome P450) from the cryptic gene cluster gave unexpected products, and that of oblBBm/oblBEv from the gene cluster of ophiobolin producers, with oblDBm as the transporter, yielded intermediate ophiobolin C through an unusual four-step oxidation process. The observation made in this study may provide a useful guideline for the elucidation of genuine biosynthetic pathways of natural products.

AB - Heterologous expression of four candidate genes found in ophiobolin gene clusters from three fungal strains was employed to elucidate the late-stage biosynthetic pathway of phytotoxin ophiobolin. Expression of oblBAc (cytochrome P450) from the cryptic gene cluster gave unexpected products, and that of oblBBm/oblBEv from the gene cluster of ophiobolin producers, with oblDBm as the transporter, yielded intermediate ophiobolin C through an unusual four-step oxidation process. The observation made in this study may provide a useful guideline for the elucidation of genuine biosynthetic pathways of natural products.

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JF - Organic Letters

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Multiple Oxidative Modifications in the Ophiobolin Biosynthesis: P450 Oxidations Found in Genome Mining

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ASJC Scopus subject areas

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