J. Jeffery, E. Abraham, G. G. Newton
May 1, 1960
Citations
0
Influential Citations
27
Citations
Journal
The Biochemical journal
Abstract
Abraham Newton showed that cephalosporin C closely resembled (D-4-amino-4-carboxy- butyl)penicillin (cephalosporin N) in some of its chemical properties but that it differed from a penicillin in others. On hydrogenolysis with Raney nickel and subsequent hydrolysis with acid cephalosporin C yielded DL-valne and D-o-aminoadipic acid, together with some L-alanine and glycine. On acid hydrolysis alone it yielded D-cx-aminoadipic acid but no penicillamine (,B-mercaptovaline). It thus appeared that cephalosporin C contained the carbon-nitrogen skeleton of penicillamine, but that it did not contain the characteristic 4-carboxy-5:5-dimethylthiazolidine ring of the true penicillins. This paper describes two degradation products of cephalosporin C which are derived from the side chain and part of the nucleus to which the latter is attached. One product is 8-amino-8-carboxyvalerylglycine The other is 2-(D-4-amino-4-carboxybutyl)thiazole-4-carboxylic acid and results from a type of fission that has not been observed with N or other penicillins. degradation