Agostini, Federica; Sinn, Ludwig; Petras, Daniel; Schipp, Christian J.; Kubyshkin, Vladimir; Berger, Allison Ann; Dorrestein, Pieter C.; Rappsilber, Juri; Budisa, Nediljko; Koksch, Beate published an article in 2021. The article was titled 《Multiomics Analysis Provides Insight into the Laboratory Evolution of Escherichia coli toward the Metabolic Usage of Fluorinated Indoles》, and you may find the article in ACS Central Science.Formula: C8H6FN The information in the text is summarized as follows:
Organofluorine compounds are known to be toxic to a broad variety of living beings in different habitats, and chem. fluorination has been historically exploited by mankind for the development of therapeutic drugs or agricultural pesticides. However, several studies so far demonstrated that, under appropriate conditions, living systems (in particular bacteria) can tolerate the presence of fluorinated mols. (e.g., amino acids analogs) within their metabolism and even repurpose them as alternative building blocks for the synthesis of cellular macromols. such as proteins. Understanding the mol. mechanism behind these phenomena would greatly advance approaches to the biotechnol. synthesis of recombinant proteins and peptide drugs. However, information about the metabolic effects of long-term exposure of living cells to fluorinated amino acids remains scarce. Hereby, the authors report the long-term propagation of Escherichia coli (E. coli) in an artificially fluorinated habitat that yielded two strains naturally adapted to live on fluorinated amino acids. In particular, the authors applied selective pressure to force a tryptophan (Trp)-auxotrophic strain to use either 4- or 5-fluoroindole as essential precursors for the in situ synthesis of Trp analogs, followed by their incorporation in the cellular proteome. Full adaptation to both fluorinated Trp analogs requires a low number of genetic mutations but is accompanied by large rearrangements in regulatory networks, membrane integrity, and quality control of protein folding. These findings highlight the cellular mechanisms behind the adaptation to unnatural amino acids and provide the mol. foundation for bioengineering of novel microbial strains for synthetic biol. and biotechnol. The authors eliminated the metabolic ability of E. coli to produce the canonical amino acid tryptophan and introduced synthesis of two fluorinated analogs in vivo using 4- and 5-fluoroindole as precursors. After reading the article, we found that the author used 5-Fluoro-1H-indole(cas: 399-52-0Formula: C8H6FN)
5-Fluoro-1H-indole(cas: 399-52-0) is a member of aromaticfluorinated building blocks. Fluorine-containing aromatics have been incorporated into crop-protection chemicals (herbicides, insecticides, fungicides). Liquid crystals, positron emission tomography, and imaging systems represent new areas where fluoroaromatics and fluoroheterocyclics have gained attention.Formula: C8H6FN
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles