Studies on viomycin. XIV. Roles of basic and cyclic moieties in the antimicrobial activity of viomycin.

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Abstract
Conformational analyses of acetylated derivatives of viomycin were performed by PMR and circular dichroism (CD) spectroscopic methods. All of the acetylviomycins showed .alpha.-methine chemical shift values over a wide region of 4.21-4.98 ppm, suggesting that all of the acetyl derivatives possess a rigid conformation at the 16-membered ring, as in viomycin. The amino acid derivatives of viomycin showed similar profiles of PMR and CD spectra. These derivatives were assumed to retain the rigid conformation. 1-Guanylviomycin, with a strongly basic group at the 1-position, was prepared, and was also found to possess a similar rigid conformation. The antimicrobial activities of 1-guanylviomycin and the acylated derivatives of viomycin toward gram-positive and gram-negative bacteria suggested that the rigid conformation is a necessary but not sufficient condition for activity. 1-Guanylviomycin showed antimicrobial activity similar to that of viomycin, confirming the previous conclusion that the 2 basic groups in viomycin are important for the antimicrobial activity. The distance between the 2 basic groups apparently is not critical.

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