Synthesis and antibacterial evaluation of phosphonic acid analogues of diaminopimelic acid

Diaminopimelic acid is an essential amino acid in the peptidoglycan of Gram-negative bacteria, mycobacteria and some Gram-positive bacteria. It can be used as a target for the development of antibacterial agents. In this article the synthesis of a series of phosphonic acid analogues of this diamino-dicarboxylic acid is described: mono- and diphosphonic acid derivatives as well as their homologues, N -alkyl analogues and some peptidyl derivatives. A phenylphosphinic derivative was also prepared. All the prepared compounds were tested for their antibacterial activity against a series of Gram-positive, Gram-negative and mycobacteria. They were also tested as possible inhibitors of the UDP-MurNAc- l -Ala-γ- d -Glu: meso -DAP synthetase. No significant biological activity was found.