ArticleAntimicrobial agents and chemotherapy2011
The antibiotic dehydrophos is converted to a toxic pyruvate analog by peptide bond cleavage in Salmonella enterica.
Article in Antimicrobial agents and chemotherapy, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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22 citing papers in PubMed, 46 citations in OpenAlex.
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- From Discovery to Manufacturing: A Quantitative Review of Phosphonates and Strategies for High-Titer Production.Microorganisms · 2026Review
- Enzymatic Synthesis of Biologically ActiveBiomolecules · 2024Article
- Integrated multi-omics unveil the impact of H-phosphinic analogs of glutamate and α-ketoglutarate on Escherichia coli metabolism.The Journal of biological chemistry · 2024Article
- Phosphonoalamides Reveal the Biosynthetic Origin of Phosphonoalanine Natural Products and a Convergent Pathway for Their Diversification.Angewandte Chemie (International ed. in English) · 2024Article
- Biosynthesis ofACS chemical biology · 2024Article
- A Desmethylphosphinothricin Dipeptide Derivative Effectively InhibitsBiomolecules · 2023Article
- Discovery of Antimicrobial Phosphonopeptide Natural Products from Bacillus velezensis by Genome Mining.Applied and environmental microbiology · 2023Article
- Antibacterial Activity of Peptide Derivatives of Phosphinothricin against Multidrug-ResistantMolecules (Basel, Switzerland) · 2023Article
- Article
- Valinophos Reveals a New Route in Microbial Phosphonate Biosynthesis That Is Broadly Conserved in Nature.Journal of the American Chemical Society · 2022Article
- Phosphonopeptides containing free phosphonic groups: recent advances.RSC advances · 2020Review
- Crossroads of Antibiotic Resistance and Biosynthesis.Journal of molecular biology · 2019Review
- Enamide Prodrugs of Acetyl Phosphonate Deoxy-d-xylulose-5-phosphate Synthase Inhibitors as Potent Antibacterial Agents.ACS infectious diseases · 2019Article
- Investigation of Amide Bond Formation during Dehydrophos Biosynthesis.ACS chemical biology · 2018Article
- Mechanistic Basis for ATP-Dependent Inhibition of Glutamine Synthetase by Tabtoxinine-β-lactam.Biochemistry · 2018Article
- Discovery of phosphonic acid natural products by mining the genomes of 10,000 actinomycetes.Proceedings of the National Academy of Sciences of the United States of America · 2015Article
- Cyanohydrin phosphonate natural product from Streptomyces regensis.Journal of natural products · 2014Article
- Genomics-enabled discovery of phosphonate natural products and their biosynthetic pathways.Journal of industrial microbiology & biotechnology · 2014Review
- Targeting DXP synthase in human pathogens: enzyme inhibition and antimicrobial activity of butylacetylphosphonate.The Journal of antibiotics · 2014Article
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
The metabolic processing of dehydrophos, a broad-spectrum peptide antibiotic containing an unusual vinyl-phosphonate moiety, was examined by using a panel of Salmonella enterica mutants deficient in peptide uptake and catabolism. Dehydrophos bioactivity is lost in opp tpp double mutants, demonstrating a requirement for uptake via nonspecific oligopeptide permeases. Dehydrophos bioactivity is also abolished in a quadruple Salmonella mutant lacking the genes encoding peptidases A, B, D, and N, showing that hydrolysis of the peptide bond is required for activity. (31)P nuclear magnetic resonance spectroscopy was used to assess the fate of dehydrophos following in vitro digestion of the antibiotic with purified PepA. The results suggest that the initial product of peptidase processing is 1-aminovinyl-phosphonate O-methyl ester. This phosphonate analogue of dehydroalanine undergoes rearrangement to the more stable imine, followed by spontaneous hydrolysis to yield O-methyl-acetylphosphonate, a structural analogue of pyruvate. This compound is a known inhibitor of pyruvate dehydrogenase and pyruvate oxidase and is probably the active species responsible for dehydrophos bioactivity.
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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.