Structure-activity relationships in the ansamycins. Molecular structure and activity of 3-carbomethoxy rifamycin S.
The X-ray and NMR structural study of 3-carbomethoxy rifamycin S5 was undertaken in order to determine whether its low antimicrobial activity was related to a conformation of the molecule which was unfavorable for interaction with bacterial DNA-dependent RNA polymerase. However, the molecule assumes a conformation similar to that of the active rifamycins. Indeed the compound was found to be active on the isolated enzyme, so that its low activity on whole bacteria has to be attributed to factors affecting its penetration through the bacterial cell wall.
D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004926:Escherichia coli / Q000187:drug effects; D047029:Lactams, Macrocyclic; D008968:Molecular Conformation; D012294:Rifamycins / Q000494:pharmacology*; D013291:Streptococcus / Q000187:drug effects; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D047029:Lactams, Macrocyclic; D012294:Rifamycins; C034952:3-carbomethoxy rifamycin S