Chemical modification of tylosin: synthesis of amino derivatives at C-20 position of tylosin and demycarosyltylosin.
Reductive aminations of the aldehyde group at C-20 position of tylosin and demycarosyltylosin (desmycosin) were carried out using primary and secondary amines in the presence of sodium cyanoborohydride. Some of these derivatives brought about higher antimicrobial and ribosome-binding activities, and the structure-activity relationship is discussed.
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007933:Leucomycins / Q000138:chemical synthesis* / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D008826:Microbial Sensitivity Tests; D012270:Ribosomes / Q000187:drug effects / Q000378:metabolism; D013329:Structure-Activity Relationship; D015645:Tylosin / Q000031:analogs & derivatives
D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D007933:Leucomycins; C032965:4'-dexydemycarosyltylosin; D015645:Tylosin