ArticleJournal of medicinal chemistry2015
Structure diversification of vancomycin through peptide-catalyzed, site-selective lipidation: a catalysis-based approach to combat glycopeptide-resistant pathogens.
Article in Journal of medicinal chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
26 citing papers in PubMed.
- Carbene-catalyzed chirality-controlled site-selective acylation of saccharides.Nature communications · 2025Article
- The Functional Mechanism and Structure-Activity Relationship of Antibacterial Peptides.Current topics in medicinal chemistry · 2025Review
- Advances, opportunities, and challenges in methods for interrogating the structure activity relationships of natural products.Natural product reports · 2024Review
- Vancomycin-Polyguanidino Dendrimer Conjugates Inhibit Growth of Antibiotic-Resistant Gram-Positive and Gram-Negative Bacteria and Eradicate Biofilm-AssociatedACS infectious diseases · 2024Article
- Vibrational Optical Activity Study of Four Antibiotic (Lipo)glycopeptides: Vancomycin, Oritavancin, Dalbavancin, and Teicoplanin.ACS omega · 2022Article
- Recent Advances in the Development of Semisynthetic Glycopeptide Antibiotics: 2014-2022.ACS infectious diseases · 2022Review
- Controlling the Site Selectivity in Acylations of Amphiphilic Diols: Directing the Reaction toward the Apolar Domain in a Model Diol and the Midecamycin AThe Journal of organic chemistry · 2022Article
- Size-Induced Inversion of Selectivity in the Acylation of 1,2-Diols.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Review
- Antimicrobial and Amyloidogenic Activity of Peptides. Can Antimicrobial Peptides Be Used against SARS-CoV-2?International journal of molecular sciences · 2020Review
- Site-switchable mono-O-allylation of polyols.Nature communications · 2020Article
- Late-Stage Diversification of Natural Products.ACS central science · 2020Review
- Experimental and Computational Studies on Regiodivergent Chiral Phosphoric Acid Catalyzed Cycloisomerization of Mupirocin Methyl Ester.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Exploration of Antibiotic Activity of Aminoglycosides, in Particular Ribostamycin Alone and in Combination With Ethylenediaminetetraacetic Acid Against Pathogenic Bacteria.Frontiers in microbiology · 2020Article
- Article
- Biological, chemical, and biochemical strategies for modifying glycopeptide antibiotics.The Journal of biological chemistry · 2019Review
- Catalytic asymmetric acetalization of carboxylic acids for access to chiral phthalidyl ester prodrugs.Nature communications · 2019Article
- Developments in Glycopeptide Antibiotics.ACS infectious diseases · 2018Article
- Site- and Stereoselective Chemical Editing of Thiostrepton by Rh-Catalyzed Conjugate Arylation: New Analogues and Collateral Enantioselective Synthesis of Amino Acids.Journal of the American Chemical Society · 2017Article
- Novel bis-cyclic guanidines as potent membrane-active antibacterial agents with therapeutic potential.Chemical communications (Cambridge, England) · 2017Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
The emergence of antibiotic-resistant infections highlights the need for novel antibiotic leads, perhaps with a broader spectrum of activity. Herein, we disclose a semisynthetic, catalytic approach for structure diversification of vancomycin. We have identified three unique peptide catalysts that exhibit site-selectivity for the lipidation of the aliphatic hydroxyls on vancomycin, generating three new derivatives 9a, 9b, and 9c. Incorporation of lipid chains into the vancomycin scaffold provides promising improvement of its bioactivity against vancomycin-resistant enterococci (Van A and Van B phenotypes of VRE). The MICs for 9a, 9b, and 9c against MRSA and VRE (Van B phenotype) range from 0.12 to 0.25 μg/mL. We have also performed a structure-activity relationship (SAR) study to investigate the effect of lipid chain length at the newly accessible G4-OH derivatization site.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.