The structure of a new macrolide antibiotic, YC-17

Total Synthesis of 10-Deoxymethynolide, the Aglycon of the Macrolide Antibiotic 10-Deoxymethymycin

“…The methymycin family of antibiotics comprises three 12-membered macrolides which have been isolated from Streptomyces species (methymycin 1a , neomethymycin 1b , and 10-deoxymethymycin 1c ) which were shown to display antibiotic activity against Gram positive bacteria. Their structures have been established through chemical degradation, spectroscopic studies, and total synthesis …”

Methymycin Biosynthesis. Isolation of P450 Monooxygenase Activity in a Cell-Free System from Streptomyces venezuelae

“…All attempts to detect the oxidation of the aglycon 5 , however, using cell-free extracts of S. venezuelae in the presence of appropriate redox cofactors were unsuccessful . By analogy to the late stage oxidation catalyzed by EryK during erythromycin biosynthesis,2a we therefore considered the possibility that the actual substrate for the hydroxylation step in methymycin biosynthesis might be the glycosylated intermediate 6 , a metabolite known as YC-17 that had previously been reported in early culture filtrates of S. venezuelae MCRL 0376 …”

Isolation and Structure Determination of Novamethymycin, a New Bioactive Metabolite of the Methymycin Biosynthetic Pathway in Streptomyces venezuelae

“…At the level of 100 μg/disk, 9 afforded an 18 mm zone of inhibition, while 18 and 20 mm zones of inhibition were observed on the same agar plate for 4 and 5 , respectively. It is noteworthy that YC-17 (16 mm zone of inhibition on the same agar plate) also showed similar activity in comparison to 4 and 5 . These results clearly indicate that the additional hydroxyl group of 9 does not alter significantly the biological activity according to the B. subtilis assay system.…”

“…It is noteworthy that YC-17 (16 mm zone of inhibition on the same agar plate) also showed similar activity in comparison to 4 and 5. 19 These results clearly indicate that the additional hydroxyl group of 9 does not alter significantly the biological activity according to the B. assay system.…”