ArticleChembiochem : a European journal of chemical biology2020
Biosynthetic Plasticity Enables Production of Fluorinated Aurachins.
Article in Chembiochem : a European journal of chemical biology, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 13 citations in OpenAlex.
- Biosynthetic incorporation of fluorinated amino acids into the nonribosomal peptide gramicidin S.RSC chemical biology · 2023Article
- Aurachins, Bacterial Antibiotics Interfering with Electron Transport Processes.Antibiotics (Basel, Switzerland) · 2023Review
- Generation of Aurachin Derivatives by Whole-Cell Biotransformation and Evaluation of Their Antiprotozoal Properties.Molecules (Basel, Switzerland) · 2023Article
- Article
- Synthesis and Biological Evaluation of Aurachin D Analogues as Inhibitors ofACS medicinal chemistry letters · 2022Article
- Hypervalent Iodine(III)-Promoted C3-H Regioselective Halogenation of 4-Quinolones under Mild Conditions.ACS omega · 2021Article
- Advances in Biosynthesis of Natural Products from Marine Microorganisms.Microorganisms · 2021Review
- Enzymatic synthesis of fluorinated compounds.Applied microbiology and biotechnology · 2021Review
- In Vitro Production and Exudation of 20-Hydroxymaytenin fromPlants (Basel, Switzerland) · 2021Article
- Bioengineering of Anti-Inflammatory Natural Products.ChemMedChem · 2021Review
- Biosynthetic Plasticity Enables Production of Fluorinated Aurachins.Chembiochem : a European journal of chemical biology · 2020Article
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Enzyme promiscuity has important implications in the field of biocatalysis. In some cases, structural analogues of simple metabolic building blocks can be processed through entire pathways to give natural product derivatives that are not readily accessible by chemical means. In this study, we explored the plasticity of the aurachin biosynthesis pathway with regard to using fluoro- and chloroanthranilic acids, which are not abundant in the bacterial producers of these quinolone antibiotics. The incorporation rates of the tested precursor molecules disclosed a regiopreference for halogen substitution as well as steric limitations of enzymatic substrate tolerance. Three previously undescribed fluorinated aurachin derivatives were produced in preparative amounts by fermentation and structurally characterized. Furthermore, their antibacterial activities were evaluated in comparison to their natural congener aurachin D.
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Registered trials
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