(.beta.-Chloro-.alpha.-aminoethyl)phosphonic acids as inhibitors of alanine racemase and D-alanine-D-alanine ligase

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Abstract
The (.beta.-chloro-, (.beta.,.beta.-dichloro-, and (.beta.,.beta.,.beta.-trichloro-.alpha.-aminoethyl)phosphonic acids have been synthesized and their inhibitory properties on the alanine racemases [EC 5.1.1.1] and the D-Ala:D-Ala ligases [EC 6.3.2.4] from Pseudomonas aeruginosa and Streptococcus faecalis have been evaluated. The monochloro and the dichloro derivatives of Ala-P exhibit a strong inhibition on the racemases of the two species tested but do not behave as suicide substrates. Only the D-Ala:D-Ala ligase of S. faecalis is inhibited by these compounds. The poor antibacterial activity observed with .beta.-chloro- and .beta.,.beta.-dichloro-Ala-P might be enhanced by the peptide-transport strategy.