title: Synthesis and biological activity of derivatives of glycopeptide antibiotics eremomycin and vancomycin nitrosated, acylated or carbamoylated at the N-terminal.
abstract: Nitrosation, carbamoylation or acylation of the glycopeptide antibiotics eremomycin or vancomycin produced series of derivatives substituted at the N-terminus of the peptides. Though the modified amino group in these derivatives is not capable of protonation, N-nitroso derivatives retain antibacterial activity in vitro and in vivo. N-Carbamoyleremomycin has low activity, and N-Cbz-eremomycin and N-Boc-eremomycin are devoid of antibacterial activity, both in vitro and in vivo.
authors.affiliation: Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow.
authors.forename: A Y
authors.initials: AY
authors.lastname: Pavlov
authors.forename: T F
authors.initials: TF
authors.lastname: Berdnikova
authors.forename: E N
authors.initials: EN
authors.lastname: Olsufyeva
authors.forename: E I
authors.initials: EI
authors.lastname: Lazhko
authors.forename: I V
authors.initials: IV
authors.lastname: Malkova
authors.forename: M N
authors.initials: MN
authors.lastname: Preobrazhenskaya
authors.forename: R T
authors.initials: RT
authors.lastname: Testa
authors.forename: P J
authors.initials: PJ
authors.lastname: Petersen
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002240:Carbohydrate Sequence; D006020:Glycopeptides; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008826:Microbial Sensitivity Tests; D008969:Molecular Sequence Data; D013203:Staphylococcal Infections / Q000188:drug therapy; D013329:Structure-Activity Relationship; D014640:Vancomycin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D006020:Glycopeptides; C053759:eremomycin; D014640:Vancomycin