title: Intramolecular proton transfer impact on antibacterial properties of ansamycin antibiotic rifampicin and its new amino analogues.
abstract: Intramolecular proton transfer in rifampicin (1) and its analogues 2-9 with the formation of zwitterions has been indicated by multinuclear NMR and crystallographic studies. Biological tests of 1-9 in combination with the analysis of ligand-protein interactions have revealed the relationship between the protonation site and extremely high antibacterial activity.
authors.affiliation: Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland.
authors.forename: Krystian
authors.initials: K
authors.lastname: Pyta
authors.forename: Piotr
authors.initials: P
authors.lastname: Przybylski
authors.forename: Barbara
authors.initials: B
authors.lastname: Wicher
authors.forename: Maria
authors.initials: M
authors.lastname: Gdaniec
authors.forename: Joanna
authors.initials: J
authors.lastname: Stefańska
mesh_terms: D000586:Amination; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D012321:DNA-Directed RNA Polymerases / Q000737:chemistry / Q000378:metabolism; D008958:Models, Molecular; D011485:Protein Binding; D011522:Protons; D012293:Rifampin / Q000031:analogs & derivatives* / Q000378:metabolism / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects; D013212:Staphylococcus epidermidis / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; D011522:Protons; D012321:DNA-Directed RNA Polymerases; D012293:Rifampin