[Peptide derivatives of tylosin-related macrolides].
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.
Korshunova
G A
GA
Sumbatian
N V
NV
Fedorova
N V
NV
Kuznetsova
I V
IV
Shishkina
A V
AV
Bogdanov
A A
AA
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
D000900:Anti-Bacterial Agents; D007933:Leucomycins; D018942:Macrolides; D009842:Oligopeptides; C052318:tylosin B; C032964:mycaminosyltylonolide; D001966:Bromine; D015645:Tylosin