ArticleACS chemical biology2016
Elucidation of the Teixobactin Pharmacophore.
Article in ACS chemical biology, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 39 papers.
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Who cites it
39 citing papers in PubMed.
- Bacterial cell envelope-targeting antibiotics.Nature reviews. Microbiology · 2026Review
- Linking molecular architecture to antibacterial functions: a chemical biology view of cyclic depsipeptides.Frontiers in chemistry · 2026Review
- Vancomycin-Teixobactin Conjugates.Journal of the American Chemical Society · 2025Article
- Drug repurposing of natural depsipeptide fromFrontiers in pharmacology · 2025Article
- Teixobactin "Swapmers" with l Tail Stereochemistry Retain Antibiotic Activity.The Journal of organic chemistry · 2024Article
- Advances, opportunities, and challenges in methods for interrogating the structure activity relationships of natural products.Natural product reports · 2024Review
- Investigation of Isobactin Analogues of Teixobactin.ACS medicinal chemistry letters · 2024Article
- Host defence peptide plectasin targets bacterial cell wall precursor lipid II by a calcium-sensitive supramolecular mechanism.Nature microbiology · 2024Article
- Supramolecular Interactions of Teixobactin Analogues in the Crystal State.The Journal of organic chemistry · 2024Article
- New Teixobactin Analogues with a Total Lactam Ring.ACS medicinal chemistry letters · 2023Article
- Synthesis and Stereochemical Determination of the Peptide Antibiotic Novo29.The Journal of organic chemistry · 2023Article
- Isobactins:Chemical science · 2022Article
- Article
- Visualizing the mode of action and supramolecular assembly of teixobactin analogues inChemical science · 2022Article
- Escaping mechanisms of ESKAPE pathogens from antibiotics and their targeting by natural compounds.Biotechnology reports (Amsterdam, Netherlands) · 2022Article
- Synthesis and application of fluorescent teixobactin analogs.Methods in enzymology · 2022Article
- Synthetic Natural Product Inspired Cyclic Peptides.ACS chemical biology · 2021Article
- Article
- Biosynthesis and Mechanism of Action of the Cell Wall Targeting Antibiotic Hypeptin.Angewandte Chemie (International ed. in English) · 2021Article
- Emerging peptide antibiotics with therapeutic potential.Medicine in drug discovery · 2021Review
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
This paper elucidates the teixobactin pharmacophore by comparing the arginine analogue of teixobactin Arg10-teixobactin to seven homologues with varying structure and stereochemistry. The roles of the guanidinium group at position 10, the stereochemistry of the macrolactone ring, and the "tail" comprising residues 1-5 are investigated. The guanidinium group is not necessary for activity; Lys10-teixobactin is more active than Arg10-teixobactin against Gram-positive bacteria in minimum inhibitory concentration (MIC) assays. The relative stereochemistry of the macrolactone ring is important. Diastereomer l-Thr8,Arg10-teixobactin is inactive, and diastereomer d-allo-Ile11,Arg10-teixobactin is less active. The macrolactone ring is critical; seco-Arg10-teixobactin is inactive. The absolute stereochemistry is not important; the enantiomer ent-Arg10-teixobactin is comparable in activity. The hydrophobic N-terminal tail is important. Truncation of residues 1-5 results in loss of activity, and replacement of residues 1-5 with a dodecanoyl group partially restores activity. These findings pave the way for developing simpler homologues of teixobactin with enhanced pharmacological properties.
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