Products of aminolysis and enzymic hydrolysis of the cephalosporins

Abstract

1. The reaction of cephalosporins with ammonia, amino acids and other simple amino compounds in weakly alkaline aqueous solutions yields labile compounds with lambda(max.) 230nm. The reaction of deacetyl- and deacetoxy-cephalosporins under similar conditions yields compounds with lambda(max.) 260nm. 2. Hydrolysis with a beta-lactamase results in the formation of compounds with lambda(max.) 230nm from deacetylcephalosporins and cephalosporins, but not from deacetoxycephalosporins. 3. These different compounds decompose to give penaldates and penamaldates derived from the side chain and the carbon atoms of the beta-lactam ring. 4. Derivatives similar to those obtained with simple amino compounds appear to be formed when cephalosporins and their analogues react with lysine polymers. 5. Some of the chemical and physical properties of the various derivatives have been studied and tentative structures for them are proposed. 6. Possible implications of the results in relation to the immunological properties of the cephalosporins are discussed.