ArticleAngewandte Chemie (International ed. in English)2017
Enzymatic C-H Oxidation-Amidation Cascade in the Production of Natural and Unnatural Thiotetronate Antibiotics with Potentiated Bioactivity.
Article in Angewandte Chemie (International ed. in English), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Three distinct strategies lead to programmable aliphatic C-H oxidation in bicyclomycin biosynthesis.Nature communications · 2025Article
- A metabologenomics strategy for rapid discovery of polyketides derived from modular polyketide synthases.Chemical science · 2025Article
- Recent developments in self-resistance gene directed natural product discovery.Natural product reports · 2020Review
- Scytodecamide from the Cultured Scytonema sp. UIC 10036 Expands the Chemical and Genetic Diversity of Cyanobactins.Chembiochem : a European journal of chemical biology · 2020Article
- Synthesis, bioactivity, and enzymatic modification of antibacterial thiotetromycin derivatives.Organic & biomolecular chemistry · 2019Article
- Extending Designed Linear Biocatalytic Cascades for Organic Synthesis.ChemCatChem · 2019Review
- The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research.Natural product reports · 2019Review
- Genome Mining and Assembly-Line Biosynthesis of the UCS1025A Pyrrolizidinone Family of Fungal Alkaloids.Journal of the American Chemical Society · 2018Article
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Authors and funding
4 authors.
Funding
Abstract
The selective activation of unreactive hydrocarbons by biosynthetic enzymes has inspired new synthetic methods in C-H bond activation. Herein, we report the unprecedented two-step biosynthetic conversion of thiotetromycin to thiotetroamide C involving the tandem oxidation and amidation of an unreactive ethyl group. We detail the genetic and biochemical basis for the terminal amidation in thiotetroamide C biosynthesis, which involves a uniquely adapted cytochrome P450-amidotransferase enzyme pair and highlights the first oxidation-amidation enzymatic cascade reaction leading to the selective formation of a primary amide group from a chemically inert alkyl group. Motivated by the ten-fold increase in antibiotic potency of thiotetroamide C ascribed to the acetamide group and the unusual enzymology involved, we enzymatically interrogated diverse thiolactomycin analogues and prepared an unnatural thiotetroamide C analogue with potentiated bioactivity compared to the parent molecule.
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