ArticleBioorganic & medicinal chemistry letters2016
A stepwise dechlorination/cross-coupling strategy to diversify the vancomycin 'in-chloride'.
Article in Bioorganic & medicinal chemistry letters, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
What it found
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Who cites it
9 citing papers in PubMed, 11 citations in OpenAlex.
- Tetrachloromaxamycins: Divergent Total Synthesis and Initial Assessments.The Journal of organic chemistry · 2024Article
- Tetrachlorovancomycin: Total Synthesis of a Designed Glycopeptide Antibiotic of Reduced Synthetic Complexity.Journal of the American Chemical Society · 2023Article
- Naturally Occurring Organohalogen Compounds-A Comprehensive Review.Progress in the chemistry of organic natural products · 2023Review
- Biological, chemical, and biochemical strategies for modifying glycopeptide antibiotics.The Journal of biological chemistry · 2019Review
- Trichlorination of a Teicoplanin-Type Glycopeptide Antibiotic by the Halogenase StaI Evades Resistance.Antimicrobial agents and chemotherapy · 2018Article
- Developments in Glycopeptide Antibiotics.ACS infectious diseases · 2018Article
- Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.Chemical reviews · 2017Review
- Halogenation of glycopeptide antibiotics occurs at the amino acid level during non-ribosomal peptide synthesis.Chemical science · 2017Article
- Living GenoChemetics by hyphenating synthetic biology and synthetic chemistry in vivo.Nature communications · 2017Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
In an effort to rapidly access vancomycin analogues bearing diverse functionality at the 6c-Cl (the 'in-chloride') position, a two-step dechlorination/cross-coupling protocol was developed. Conditions for efficient cross-coupling of the relatively unreactive 6c-Cl group were found that ensure high conversion with minimal product decomposition. A set of 2c-dechloro-6c-functionalized vancomycin derivatives was prepared, and antibiotic activities of the compounds were evaluated against a panel of vancomycin-resistant and vancomycin-susceptible strains. Results from biological testing further underscore the steric sensitivity of vancomycin's binding pocket.
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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.