Publication: Identification of biosynthetic genes for the β-carboline alkaloid kitasetaline and production of the fluorinated derivatives by heterologous expression
Issued Date
2019-05-10
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ISSN
14765535
13675435
13675435
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2-s2.0-85061842685
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Mahidol University
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SCOPUS
Bibliographic Citation
Journal of Industrial Microbiology and Biotechnology. Vol.46, No.5 (2019), 739-750
Suggested Citation
Shohei Ueda, Haruo Ikeda, Takushi Namba, Yukinori Ikejiri, Yuri Nishimoto, Masayoshi Arai, Takuya Nihira, Shigeru Kitani Identification of biosynthetic genes for the β-carboline alkaloid kitasetaline and production of the fluorinated derivatives by heterologous expression. Journal of Industrial Microbiology and Biotechnology. Vol.46, No.5 (2019), 739-750. doi:10.1007/s10295-019-02151-z Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/50180
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Title
Identification of biosynthetic genes for the β-carboline alkaloid kitasetaline and production of the fluorinated derivatives by heterologous expression
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Abstract
© 2019, Society for Industrial Microbiology and Biotechnology. β-Carboline alkaloids exhibit a broad spectrum of pharmacological and biological activities and are widely distributed in nature. Genetic information on the biosynthetic mechanism of β-carboline alkaloids has not been accumulated in bacteria, because there are only a few reports on the microbial β-carboline compounds. We previously isolated kitasetaline, a mercapturic acid derivative of a β-carboline compound, from the genetically modified Kitasatospora setae strain and found a plausible biosynthetic gene cluster for kitasetaline. Here, we identified and characterized three kitasetaline (ksl) biosynthetic genes for the formation of the β-carboline core structure and a gene encoding mycothiol-S-conjugate amidase for the modification of the N-acetylcysteine moiety by using heterologous expression. The proposed model of kitasetaline biosynthesis shows unique enzymatic systems for β-carboline alkaloids. In addition, feeding fluorotryptophan to the heterologous Streptomyces hosts expressing the ksl genes led to the generation of unnatural β-carboline alkaloids exerting novel/potentiated bioactivities.