7-Aminocephalo sporanic acid

A more traditional cephalosporin analogue is cephapirin (22). It was made by reacting 7-aminocephalo-sporanic acid with bromoacetyl chloride to give amide 21. The halo group was displaced by 4-thiopyridine... 

This oxidative deamination catalyzed by immobilized enzymes is part of the 7-aminocephalosporanic acid (7-ACA) process. Ketoadipinyl-7-aminocephalo-sporanic acid decarboxylates in situ in the presence of H2O2, which is formed by the... 

In the course of studies on the Brotzu strain of Cephalosporium, Abraham and Newton detected small quantities of a second antibiotic, cephalosporin C. Painstaking work proved it to be chemically similar to penicillin N, but not a penicillin. It had pronounced gramnegative activity, was more stable to acid, and was not destroyed by penicillinase. It possessed the same a-aminoadipyl side chain as a new penicillin, but the nucleus was 7-aminocephalo-sporanic acid (7-AC A). 7-AC A contains a six-membered 1,3-dihydrothiazine ring instead of the five-membered thiazole ring in 6-APA. The structures of 6-APA and 7-ACA are shown in Fig. 24.31. 

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