The Prasinomycins: Antibiotics containing Phosphorus

Additional Antibiotic Inhibitors of Peptidoglycan Synthesis

“…L~ipid moenomycin, and prasinomycin as is that from B. stearothermophilus, since in vivo E. ccli and other gram-negative bacteria are resistant to these antibiotics (19,32,34). These data suggest that the relative resistance of the gram-negative organisms must be due to a permeability barrier.…”

“…In this investigation, the effects of several lipid-containing antibiotics, diumycin (19), moenomycin (33), prasinomycin (34), and janiemycin (21), as well as the peptide antibiotics nisin (18) and subtilin (9), on peptidoglycan synthesis catalyzed by particulate enzyme preparations from Bacillus stearothermophilus and Escherichia coli were studied. While this work was in progress, the effects of two of these, prasinomycin and moenomycin, were also studied by Lugtenberg et al (14).…”

Moenomycin family antibiotics: chemical synthesis, biosynthesis, and biological activity

“…These include: the absence/presence of the branching glucose unit D; the structure of sugar units C and/or E, which can be either N-acetyl glucosamine or its 6-deoxy version, chinovosamine; the stereochemistry and further functionalization of position 4 of moenuronamide unit F (D- galacto versus D- gluco ; there is an axial methyl group in the latter case); finally, in the majority of moenomycins the carboxylic acid group of galactopyranuronic acid unit B can be either linked to a 2-aminocyclopentane-1,3-dione (C 5 N) chromophore unit A, or converted into a carboxamide, or extended with glycine. (The latter modification, found in moenomycins G and H44 as well as some prasinomycins45, was inferred only from degradation studies and thus more rigorous structural analysis is required to confirm it). Four minor components of the flavomycin complex, 6-9 , were also recently identified with the help of high-resolution tandem mass-spectrometry 46.…”

Molecular Association of the Antibiotic Prasinomycins

“…HE prasinomycins are a family of closely related T antibiotics isolated from Streptomyces prasinus (1). In aqueous solvents the prasinomycins associate, forming two aggregates with molecular weights of approximately 31,000 and 61,000.…”