Structure and biological activity of ascamycin, a new nucleoside antibiotic.
A newly isolated strain of Streptomyces sp. produces a new nucleoside antibiotic, ascamycin and the corresponding dealanyl derivative. The structure of ascamycin was determined to be 2-chloro-9-beta-[5-O-(N-L-alanyl)sulfamoyl-D-ribofuranosyl]-adenine. Remarkable selective toxicity of ascamycin compared to the dealanyl derivative was accounted for on the basis of a dealanylating enzyme present in the envelope of sensitive bacteria. After dealanylation, it becomes permeable to cell membrane.
D000241:Adenosine / Q000302:isolation & purification / Q000494:pharmacology / Q000031:analogs & derivatives; D000900:Anti-Bacterial Agents / Q000302:isolation & purification*; D004353:Drug Evaluation, Preclinical; D004926:Escherichia coli / Q000187:drug effects / Q000378:metabolism; D010649:Phenylalanine / Q000378:metabolism; D013302:Streptomyces; D013329:Structure-Activity Relationship; D014974:Xanthomonas / Q000187:drug effects
D000900:Anti-Bacterial Agents; D010649:Phenylalanine; C042369:ascamycin; D000241:Adenosine