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Identification of biosynthetic genes for the β-carboline alkaloid kitasetaline and production of the fluorinated derivatives by heterologous expression.
- Source :
-
Journal of Industrial Microbiology & Biotechnology . May2019, Vol. 46 Issue 5, p739-750. 12p. 4 Diagrams, 1 Chart, 2 Graphs. - Publication Year :
- 2019
-
Abstract
- 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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ALKALOIDS
*PYRROLIZIDINES
*GENES
*GENE clusters
*ACID derivatives
*STREPTOMYCES
Subjects
Details
- Language :
- English
- ISSN :
- 13675435
- Volume :
- 46
- Issue :
- 5
- Database :
- Academic Search Index
- Journal :
- Journal of Industrial Microbiology & Biotechnology
- Publication Type :
- Academic Journal
- Accession number :
- 136405029
- Full Text :
- https://doi.org/10.1007/s10295-019-02151-z