fosfomycin [Drug Class]

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Accession ARO:0000025
Synonym(s)phosphomycin phosphonomycin (1R,2S)-1,2-epoxy-propylphosphonic acid
DefinitionFosfomycin (also known as phosphomycin and phosphonomycin) is a broad-spectrum antibiotic produced by certain Streptomyces species. It is effective on gram positive and negative bacteria as it targets the cell wall, an essential feature shared by both bacteria. Its specific target is MurA (MurZ in E.coli), which attaches phosphoenolpyruvate (PEP) to UDP-N-acetylglucosamine, a step of commitment to cell wall synthesis. In the active site of MurA, the active cysteine molecule is alkylated which stops the catalytic reaction.
Classification2 ontology terms | Show
Parent Term(s)1 ontology terms | Show
Sub-Term(s)
30 ontology terms | Show
+ determinant of fosfomycin resistance confers_resistance_to_drug_class
+ Acinetobacter baumannii AbaF confers_resistance_to_drug_class
+ fosfomycin thiol transferase [AMR Gene Family] confers_resistance_to_drug_class
+ fosC phosphotransferase family [AMR Gene Family] confers_resistance_to_drug_class
+ Fom phosphotransferase family [AMR Gene Family] confers_resistance_to_drug_class
+ GlpT [AMR Gene Family] confers_resistance_to_drug_class
+ UhpT [AMR Gene Family] confers_resistance_to_drug_class
+ UhpA [AMR Gene Family] confers_resistance_to_drug_class
+ PtsI phosphotransferase [AMR Gene Family] confers_resistance_to_drug_class
+ cya adenylate cyclase [AMR Gene Family] confers_resistance_to_drug_class
+ murA transferase [AMR Gene Family] confers_resistance_to_drug_class
+ major facilitator superfamily (MFS) antibiotic efflux pump [AMR Gene Family] confers_resistance_to_drug_class
+ FomA confers_resistance_to_antibiotic
+ FomB confers_resistance_to_antibiotic
+ FosC confers_resistance_to_antibiotic
+ FosA confers_resistance_to_antibiotic
+ FosB confers_resistance_to_antibiotic
+ FosX confers_resistance_to_antibiotic
+ Escherichia coli GlpT with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic
+ Escherichia coli UhpT with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic
+ Escherichia coli UhpA with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic
+ Escherichia coli PtsI with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic
+ Escherichia coli CyaA with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic
+ Staphylococcus aureus GlpT with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic
+ Staphylococcus aureus UhpT with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic
+ Staphylococcus aureus FosB confers_resistance_to_antibiotic
+ FosA6 confers_resistance_to_antibiotic
+ FosA7 confers_resistance_to_antibiotic
+ mdtG confers_resistance_to_antibiotic
+ fosfomycin sensitive pyruvyl transferase (murA) targeted_by_antibiotic
Publications

Fillgrove KL, et al. 2007. Biochemistry 46(27): 8110-8120. Structure and mechanism of the genomically encoded fosfomycin resistance protein, FosX, from Listeria monocytogenes. (PMID 17567049)

Hendlin D, et al. 1969. Science 166(901): 122-123. Phosphonomycin, a new antibiotic produced by strains of streptomyces. (PMID 5809587)

Brown ED, et al. 1994. Biochemistry 33(35): 10638-10645. Detection and characterization of a phospholactoyl-enzyme adduct in the reaction catalyzed by UDP-N-acetylglucosamine enolpyruvoyl transferase, MurZ. (PMID 8075064)

Skarzynski T, et al. 1996. Structure 4(12): 1465-1474. Structure of UDP-N-acetylglucosamine enolpyruvyl transferase, an enzyme essential for the synthesis of bacterial peptidoglycan, complexed with substrate UDP-N-acetylglucosamine and the drug fosfomycin. (PMID 8994972)

Pakhomova S, et al. 2008. J Biol Chem 283(42): 28518-28526. Crystal structure of fosfomycin resistance kinase FomA from Streptomyces wedmorensis. (PMID 18701452)