Isolation of cephalosporin C, a penicillin-like antibiotic containing d-α-aminoadipic acid

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Abstract
Crude preparations of cephalosporin N, a hydrophilic penicillin, were found to contain a second hydrophilic antibiotic. This substance, named cephalosporin C, was isolated as a crystalline Na salt. Mixtures of cephalosporin C and cephalosporin N penillic acid were completely resolved by chromatography on an anion-ex-change resin and by countercurrent distribution in a phenol-water system containing acetic acid. Mixtures of cephalosporin C and cephalosporin N were resolved on paper chromatograms and partly resolved on an ion-exchange resin. Cephalosporin C was provisionally assigned the molecular formula C16H21O8N3S. It behaves as a monoaminodicarboxylic acid. It shows an absorption maximum at 260 m[mu] and its infrared spectrum contains a band at 5.61 [mu]. Cephalosporin C shows similar activity to Salmonella typhi and Staphylococcus aureus. Against these organisms its activity is about 10% of that of cephalosporin N. Cephalosporin C is stable in dilute acid but readily inactivated by dilute alkali. It is insensitive to some preparations of peni-cillinase, but not to others. A new enzyme C-cephalosporinase, may therefore catalyse its inactivation.