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Title: Identification of biosynthetic genes for the β-carboline alkaloid kitasetaline and production of the fluorinated derivatives by heterologous expression
Authors: Shohei Ueda
Haruo Ikeda
Takushi Namba
Yukinori Ikejiri
Yuri Nishimoto
Masayoshi Arai
Takuya Nihira
Shigeru Kitani
Osaka University
Kochi University
Mahidol University
Kitasato University
Keywords: Biochemistry, Genetics and Molecular Biology;Chemical Engineering;Immunology and Microbiology
Issue Date: 10-May-2019
Citation: Journal of Industrial Microbiology and Biotechnology. Vol.46, No.5 (2019), 739-750
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.
ISSN: 14765535
Appears in Collections:Scopus 2019

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