Association of 6-oxo-piperidine-2-carboxylic acid with penicillin V. Production on Penicillium chrysogenum fermentations

J Antibiot (Tokyo). 1980 Nov;33(11):1348-51. doi: 10.7164/antibiotics.33.1348.

Abstract

Analysis of a 13C NMR spectrum of a concentrated broth from Penicillium chrysogenum fermentation revealed the presence of penicillin V and 6-oxo-piperidine-2-carboxylic acid(1) as the principal constituents. The latter lactam, identical to an authentic sample prepared by the cyclization of alpha-aminoadipic acid was present to the extent of 28 mol% of penicillin V. The lactam isolated form the broth was nearly racemic, having a slight excess of the L-isomer. This isolation provides further evidence regarding the biosynthetic precursors of the hydrophobic penicillins.

MeSH terms

  • Carbon Radioisotopes
  • Culture Media / analysis
  • Fermentation*
  • Lactams / analysis
  • Lactams / biosynthesis*
  • Lactams / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Penicillin V / analysis
  • Penicillin V / biosynthesis*
  • Penicillin V / isolation & purification
  • Penicillium / metabolism*
  • Penicillium chrysogenum / metabolism*
  • Pipecolic Acids*

Substances

  • 6-oxopiperidine-2-carboxylic acid
  • Carbon Radioisotopes
  • Culture Media
  • Lactams
  • Pipecolic Acids
  • Penicillin V