Reactive acyl dipeptides as potential penicillin analogues. Part II. N-(Acylglycyl)-5-oxo-pyrrolidine-2-carboxylic acids and N-(acylglycyl)-5,5-dimethyl-2-oxothiazolidine-4-carboxylic acids
Abstract
Reaction of acylglycine p-nitrophenyl esters with the N-sodio-derivative of benzyl 5-oxopyrrolidine-2-carboxylate gave, after hydrogenolysis, N-(acylglycyl)-5-oxopyrrolidine-2-carboxylic acids. N-(Acylglycyl)-5,5-dimethyl-2-oxothiazolidine-4-carboxylic acids were similarly prepared from benzyl 5,5-dimethyl-2-oxothiazolidine-4-carboxylate. Both types of acid could be regarded, like penicillin, as acyl dipeptides containing a reactive peptide bond, but they exhibited only very slight antibacterial activity.