Chemical and biological aspects of a new family of phosphorus‐containing antibiotics

Abstract

The chemical, physical, and biological properties of a group of phosphorus‐containing antibiotics are reviewed. Included in this family of antibiotics are the following compounds or mixtures of compounds: diumycin, macarbomycin, moenomycin, prasinomycin, 803GRP, 11,837RP, and 19,402RP. Among the aspects discussed are: antimicrobial activity in vitro, long duration of activity, toxicity, use in animal nutrition, cross resistance, mode of action, chemical and physical properties, and degradation studies.

Biosynthesis of the peptidoglycan of Escherichia coli K‐12

“…ThefD, values of these compounds were 0.01-0.1 pg/ml, except for enduracidin which was a less efficient inhibitor. These results further stress the fact, substantiated [6], that close analogies exist between these different compounds. As expected from the results in [7] mecillmam had no inhibiting effect on the reaction.…”

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

“… a A strict comparison of the MICs should not be made since the experimental conditions were not the same 9, 23, 38, 40, 49, 80, 141, 143, 146 b

Macarbomycin.

c

Prasinomycin.

d

Teichomycin A 1 .

e

803RP.

f

Piperacillin-resistant strain.

g

Disruption of pbp2a gene.

h

imp ( i ncreased m embrane p ermeability) strains.

i

Not determined.

…”

“…As a result, the molecular mechanisms of moenomycin action are now clearer, and better chemical and biological tools have been developed to generate novel phosphoglycolipids for various purposes. In the past, several reviews have covered the occurrence of moenomycin antibiotics in nature as well as their chemistry and biology 4,8,9,12,21,23-30. Some of these reviews are now outdated, while others do not provide a complete overview of the tripartite complexity of chemical manipulations, biosynthesis and the biological properties of moenomycins.…”

Polymerization by transglycosylation in the biosynthesis of the peptidoglycan of Escherichia coli K 12 and its inhibition by antibiotics

“…MIC values from 8-250 pg/ml were reported when moenomycin and 11837 R.P. were tested on E. coli [22] . These high values are presumably due to difficulties of penetration.…”

“…These high values are presumably due to difficulties of penetration. With gram-positive bacteria MIC values from 0.005-0.3 pg/ml were found [22]. The inhibition of the transglycosylation reaction by these antibiotics is thus probably the main mechanism responsible for their antibacterial activity.…”