The biosynthetic implications of acetate and glutamate incorporation into (3R,5R)-carbapenam-3-carboxylic acid and (5R)-carbapen-2-em-3-carboxylic acid by Serratia sp

J Antibiot (Tokyo). 1988 Sep;41(9):1231-42. doi: 10.7164/antibiotics.41.1231.

Abstract

Two new beta-lactams have been isolated from strains of Serratia and Erwinia sp. and identified as (3R,5R)- and (3S,5R)-carbapenam-3-carboxylic acid. These novel carbapenams lack antibacterial activity, are resistant to both beta-lactamases I and II from Bacillus cereus and are not detected by the lactamase induction assay. Radiolabelled and stable isotope experiments have established that both metabolites together with the antibiotic 5R-carbapenem-3-carboxylic acid are glutamate and acetate derived. A number of possible pathways for the biosynthesis of these compounds as well as their relationship to the more complex members of the carbapenem family of beta-lactam antibiotics are discussed.

MeSH terms

  • Acetates / metabolism*
  • Anti-Bacterial Agents / biosynthesis*
  • Carbapenems*
  • Carbon Isotopes
  • Carbon Radioisotopes
  • Chemical Phenomena
  • Chemistry
  • Chromatography, High Pressure Liquid
  • Glutamates / metabolism*
  • Lactams*
  • Serratia / metabolism*
  • Stereoisomerism

Substances

  • Acetates
  • Anti-Bacterial Agents
  • Carbapenems
  • Carbon Isotopes
  • Carbon Radioisotopes
  • Glutamates
  • Lactams
  • carbapenam-3-carboxylic acid
  • carbapenem-3-carboxylic acid