Biological conversion of erythronolide B,an intermediate of erythromycin biogenesis,into new "hybrid" macrolide antibiotics.

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Abstract
Transformation of erythronolide B to new antibiotics was attempted by feeding this compound during the fermentation of Streptomyces antibioticus ATCC 31771, a blocked mutant of an oleandomycin producing strain. As a result, 4 new active compounds were obtained with hybrid structures between erythromycin and oleandomycin. They were identified as 3-O-oleandrosyl-5-O-desosaminyl-15-hydroxyerythronolide B, 3-O-oleandrosyl-5-O-desosaminylerythronolide B, 3-O-oleandrosyl-5-O-desosaminyl-(8S)-8-hydroxyerythronolide B and 3-O-oleandrosyl-5-O-desosaminyl(8R)-8,19-epoxyerythronolide B. They were less active against bacteria, but more stable to acid, than erythromycin A. Based on their relative biogenetical relationships and their elucidated structures, some hypotheses about the late stages of oleandomycin biosynthesis are inferred.