Abstract

Tylosin is a 16-membered macrolide antibiotic, composed of a substituted lactone (tylonolide), an amino sugar (mycaminose) and two neutral sugars (mycinose and mycarose' (Scheme 1). It is produced on an industrial scale and is widely used as a feed additive and as a therapeutic agent in the treatment of mycoplasmosis in poultry and livestock. An advantage of this antibiotic is that it does not cause resistance because it is not used in human medicine.' The exact molecular structure of tylosin (molecular mass 916) together with the principal assignment of its I3C NMR spectrum was established in 1975 based on the analysis and identification of the products of mild acid hydrolysis3 and on 13C NMR data for related subs t a n c e ~ . ~ The crystal structure and the absolute configuration of protynolide,' a 16-membered lactone

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