ArticleACS infectious diseases2023
Total Synthesis and Structure Assignment of the Relacidine Lipopeptide Antibiotics and Preparation of Analogues with Enhanced Stability.
Article in ACS infectious diseases, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- False Novelty in Antibacterial Natural-Product Discovery: Rediscovery, Structural Misassignment, and a Checkpoint Framework for Early Verification.Pharmaceuticals (Basel, Switzerland) · 2026Review
- Linking molecular architecture to antibacterial functions: a chemical biology view of cyclic depsipeptides.Frontiers in chemistry · 2026Review
- Exploring Structure-Activity Relationships and Modes of Action of Laterocidine.ACS central science · 2024Article
- Discovery and Derivatization of Tridecaptin Antibiotics with Altered Host Specificity and Enhanced Bioactivity.ACS chemical biology · 2024Article
- Steglich esterification: A versatile synthetic approach toward the synthesis of natural products, their analogues/derivatives.Heliyon · 2024Article
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Authors and funding
11 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The unabated rise of antibiotic resistance has raised the specter of a post-antibiotic era and underscored the importance of developing new classes of antibiotics. The relacidines are a recently discovered group of nonribosomal lipopeptide antibiotics that show promising activity against Gram-negative pathogens and share structural similarities with brevicidine and laterocidine. While the first reports of the relacidines indicated that they possess a C-terminal five-amino acid macrolactone, an N-terminal lipid tail, and an overall positive charge, no stereochemical configuration was assigned, thereby precluding a full structure determination. To address this issue, we here report a bioinformatics guided total synthesis of relacidine A and B and show that the authentic natural products match our predicted and synthesized structures. Following on this, we also synthesized an analogue of relacidine A wherein the ester linkage of the macrolactone was replaced by the corresponding amide. This analogue was found to possess enhanced hydrolytic stability while maintaining the antibacterial activity of the natural product in both
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