Azapeptide analogs of acyl-D-ala-D-ala bearing α-azaamino acid moiety in the penultimate position have been designed and synthesized as inhibitors of D-alanyl-D-alanyl transpeptidases. The selective N-nitration of the C-terminal amide bond in the pre...
Azapeptide analogs of acyl-D-ala-D-ala bearing α-azaamino acid moiety in the penultimate position have been designed and synthesized as inhibitors of D-alanyl-D-alanyl transpeptidases. The selective N-nitration of the C-terminal amide bond in the presence of a free carboxy group was investigated under several reaction conditions; N-nitro-or Nitroso-azapeptides proved to be too unstable to isolate. However N-nitrosation of methyl ester of azapeptide was successfully accomplished to give the selective nitroso product with an excess of N₂O₄.