ArticleJournal of the American Chemical Society2011
Chemical synthesis enables biochemical and antibacterial evaluation of streptolydigin antibiotics.
Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 46 citations in OpenAlex.
- Mediation of metal chelation in cysteine-derived tetramate systems.Chemical science · 2021Article
- Lewis Base-Brønsted Acid-Enzyme Catalysis in Enantioselective Multistep One-Pot Syntheses.Angewandte Chemie (International ed. in English) · 2021Article
- Functionalised bicyclic tetramates derived from cysteine as antibacterial agents.Organic & biomolecular chemistry · 2019Article
- Design, synthesis and microbiological evaluation of ampicillin-tetramic acid hybrid antibiotics.The Journal of antibiotics · 2017Article
- X-Ray Crystallographic Analysis, EPR Studies, and Computational Calculations of a Cu(II) Tetramic Acid Complex.Bioinorganic chemistry and applications · 2017Article
- Homoserine as an Aspartic Acid Precursor for Synthesis of Proteoglycan Glycopeptide Containing Aspartic Acid and a Sulfated Glycan Chain.The Journal of organic chemistry · 2016Article
- Gastrointestinal localization of metronidazole by a lactobacilli-inspired tetramic acid motif improves treatment outcomes in the hamster model of Clostridium difficile infection.The Journal of antimicrobial chemotherapy · 2015Article
- Stereochemical assignment of the protein-protein interaction inhibitor JBIR-22 by total synthesis.Angewandte Chemie (International ed. in English) · 2015Article
- Stereochemical Assignment of the Protein-Protein Interaction Inhibitor JBIR-22 by Total Synthesis.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2015Article
- Antibacterial barbituric acid analogues inspired from natural 3-acyltetramic acids; synthesis, tautomerism and structure and physicochemical property-antibacterial activity relationships.Molecules (Basel, Switzerland) · 2015Article
- Mycobacterium tuberculosis is resistant to streptolydigin.Tuberculosis (Edinburgh, Scotland) · 2013Article
- Total synthesis of (-)-tirandamycin C.Organic letters · 2012Article
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
Abstract
Inhibition of bacterial transcription represents an effective and clinically validated anti-infective chemotherapeutic strategy. We describe the evolution of our approach to the streptolydigin class of antibiotics that target bacterial RNA polymerases (RNAPs). This effort resulted in the synthesis and biological evaluation of streptolydigin, streptolydiginone, streptolic acid, and a series of new streptolydigin-based agents. Subsequent biochemical evaluation of RNAP inhibition demonstrated that the presence of both streptolic acid and tetramic acid subunits was required for activity of this class of antibiotics. In addition, we identified 10,11-dihydrostreptolydigin as a new RNAP-targeting agent, which was assembled with high synthetic efficiency of 15 steps in the longest linear sequence. Dihydrostreptolydigin inhibited three representative bacterial RNAPs and displayed in vitro antibacterial activity against S. salivarius . The overall increase in synthetic efficiency combined with substantial antibacterial activity of this fully synthetic antibiotic demonstrates the power of organic synthesis in enabling design and comprehensive in vitro pharmacological evaluation of new chemical agents that target bacterial transcription.
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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.