The structure of cephalosporin C

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Abstract
Cephalosporin C (C16H21O8N3S) has been degraded by hydrolysis, hydrogenolysis and oxidation. Degradation products obtained from one half of the molecule include carbon dioxide, [delta] -amino- [delta] -carboxyvalerylglycine, 2-(D-4''-amino-4''-carboxy-n-butyl)thiazole-4-carboxylic acid and [alpha][beta]-diaminopropionic acid. Degradation products obtained from the second half of the molecule include acetic acid, gamma-hydroxyvaline, [alpha]-oxoisovaleric acid and l-hydroxy-2-methylprop-l-ene-1-carboxylic acid lactone. Consideration of the degradation products, together with the ultraviolet- and infrared-absorption spectra, nuclear-magnetic-resonance spectrum and behavior on electrometric titration of cephalosporin C, has led to a definitive structure for the antibiotic. This structure contains a fused [beta]-lactam-dihydrothiazine ring system in place of the [beta]-lactam-thiazolidine ring system of the penicillins. Cephalosporin Cc, formed from cephalosporin C in 0.1 N hydrochloric acid at room temperature, is deacetylcephalosporin C lactone. The biogenesis of cephalosporin C is considered in relation to that of cephalosporin N and other penicillins.