Chemical modification of tylosin. Thioether derivatives of tylosin and demycarosyltylosin.

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.

Syntheses and antimicrobial activities of 9-O-acyl derivatives of tylosin and demycarosyltylosin.

A high prevalence of tylosin resistance among Staphylococcus aureus strains isolated from bovine mastitis

The macrolides appear to have considerable effects for treatment of bovine mastitis because of excellent diffusion into the mammary gland, long half-life, low protein binding, high intracellular concentration and lipid solubility. Acquired resistance to macrolides in Staphylococcus aureus is primarily related to target-site modification through acquisition of an erm gene. In t...

Chemical modification of tylosin.

20-Homo tylosin, 20-nor tylosin, 20-deoxy-19,20-didehydro tylosin (6-vinyl tylosin) and 2",3"-didehydro-3"-deoxy tylosin were prepared by multi-step procedures. 20-Homo tylosin was about twice less active than tylosin while the other compounds exhibited very weak antibacterial activity.

Physico-chemical properties of new acyl derivatives of tylosin produced by microbial transformation.

By microbial transformation of tylosin (I), the following eight new acyl derivatives were obtained: 3-acetyltylosin (II), 3-propionyltylosin (III), 4"-butyryltylosin (IV), 4"-isovaleryltylosin (V), 3-acetyl-4"-butyryltylosin (VI), 3-acetyl-4"-isovaleryltylosin (VII), 3-propionyl-4"-butyryltylosin (VIII) and 3-propionyl-4"-isovaleryltylosin (IX).