title: [Peptide derivatives of tylosin-related macrolides].
abstract: Approaches to the synthesis of model compounds based on the tylosin-related macrolides desmycosin and O-mycaminosyltylonolide were developed using specially designed peptide derivatives of macrolide antibiotics to study the conformation and topography of the nascent peptide chain in the ribosome tunnel. A method for selective bromoacetylation of desmycosin at the hydroxyl group of mycinose was developed, which involves preliminary acetylation of mycaminose. The reaction of the 4"-bromoacetyl derivative of the antibiotic with cesium salts of the dipeptide Boc-Ala-Ala-OH and the hexapeptide MeOTr-Gly-Pro-Gly-Pro-Gly-Pro-OH led to the corresponding peptide derivatives of desmycosin. The protected peptides Boc-Ala-Ala-OH, Boc-Ala-Ala-Phe-OH, and Boc-Gly-Pro-Gly-Pro-Gly-Pro-OH were condensed with the C23-hydroxyl group of O-mycaminosyltylonolide.
authors.forename: G A
authors.initials: GA
authors.lastname: Korshunova
authors.forename: N V
authors.initials: NV
authors.lastname: Sumbatian
authors.forename: N V
authors.initials: NV
authors.lastname: Fedorova
authors.forename: I V
authors.initials: IV
authors.lastname: Kuznetsova
authors.forename: A V
authors.initials: AV
authors.lastname: Shishkina
authors.forename: A A
authors.initials: AA
authors.lastname: Bogdanov
mesh_terms: D000107:Acetylation; D000595:Amino Acid Sequence; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001966:Bromine / Q000737:chemistry; D007933:Leucomycins / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D015645:Tylosin / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D007933:Leucomycins; D018942:Macrolides; D009842:Oligopeptides; C052318:tylosin B; C032964:mycaminosyltylonolide; D001966:Bromine; D015645:Tylosin