Studies on Viomycin. XIV. Roles of Basic and Cyclic Moieties in the Antimicrobial Activity of Viomycin

概要

論文の詳細を見る
Conformational analyses of acetylated derivatives of viomycin were performed by proton magnetic resonance (PMR) and circular dichroism (CD) spectroscopic methods. All of the acetylviomycins showed α-methine chemical shift values over a wide region from 4.21 to 4.98 ppm, suggesting that all of the acetyl derivatives possess a rigid conformation at the sixteen-membered ring, as in viomycin. The amino acid derivatives of viomycin showed similar profiles of PMR and CD spectra. These derivatives were thus 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 two basic groups in viomycin are important for the antimicrobial activity. It was also concluded that the distance between the two basic groups is not critical.
公益社団法人日本薬学会の論文
1979-11-25