ArticleJournal of the American Chemical Society2024
Total Synthesis and Stereochemical Assignment of Enteropeptin A.
Article in Journal of the American Chemical Society, 2024. 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.
- Reprogramming RiPP scaffolds through skeletal editing unlocks chemical space.Chemical science · 2026Article
- Unified Access to Biaryl-Bridged Linkages Unlocks Structural Diversification of Noncanonical Cyclic Peptides.Journal of the American Chemical Society · 2026Article
- Assigning the stereochemistry of natural products by machine learning.Journal of cheminformatics · 2026Article
- Evolution of a Strategy for the Unified Synthesis of Enteropeptin Sactipeptides.The Journal of organic chemistry · 2026Article
- Catalytic Markovnikov Hydrothiolation of Dehydroamino Acids: Unified Total Synthesis of Enteropeptin Sactipeptides.Journal of the American Chemical Society · 2025Article
- Diverse thioether macrocyclized peptides through a radical SAM maturase.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
- Exploring thurincin H as a biotechnologically relevant sactipeptide after fifteen years of research.Archives of microbiology · 2025Review
- Total Synthesis of (±)-3-Thiaglutamate.Tetrahedron letters · 2024Article
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4 authors.
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Abstract
The total synthesis and structural elucidation of the antimicrobial sactipeptide enteropeptin A is reported. Enteropeptin A contains a thioaminoketal group with an unassigned stereochemical configuration that is embedded in a highly unusual thiomorpholine ring. In this synthesis, a linear peptide containing a dehydroamino acid and a pendant cysteine residue is subjected to Markovnikov hydrothiolation by a dithiophosphoric acid catalyst. This cyclization reaction forms the central thiomorpholine ring found in the enteropeptins. Both diastereomers at the unassigned thioaminoketal stereocenter of enteropeptin A were prepared, and their comparison to an authentic standard allowed for the unambiguous stereochemical assignment of the natural product to be of the D configuration. This inaugural total synthesis of enteropeptin A represents the first total synthesis of a sactipeptide reported to date. Moreover, the strategy disclosed herein serves as a general platform for the synthesis of stereochemically defined thiomorpholine-containing peptides, which may enable the discovery of new cyclic peptide antibiotics.
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