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. 1974 Feb;71(2):417–421. doi: 10.1073/pnas.71.2.417

Inhibition of Bacterial Growth by β-Chloro-D-Alanine

James M Manning 1, Nancy E Merrifield 1, Wanda M Jones 1, Emil C Gotschlich 1
PMCID: PMC388017  PMID: 4150023

Abstract

The D- and L-isomers of β-chloroalanine inhibit the growth of Diplococcus pneumoniae, Streptococcus pyogenes, Bacillus subtilis, and Escherichia coli. With pneumococcus the inhibition by β-chloro-D-alanine is completely prevented by either D-alanine or D-alanyl-D-alanine, while L-alanine is not effective in preventing the inhibition. The inhibition of growth by β-chloro-L-alanine is not affected by D-alanine and is only partially prevented by high concentrations of L-alanine. The intracellular free alanine in untreated E. coli and B. subtilis is about 95% in the D-configuration while the free intracellular alanine in both organisms after treatment with β-chloro-D-alanine is predominantly the L-isomer. These results suggested that the β-chloroamino acid inactivates alanine racemase (EC 5.1.1.1). Indeed, when extracts of E. coli or B. subtilis were treated with β-chloro-D-alanine, the activities of alanine racemase and of D-glutamate-D-alanine transaminase were found to be 90-95% inhibited. Studies with mice have shown that β-chloro-D-alanine is an effective antibacterial agent in vivo againt D. pneumoniae, S. pyogenes, and E. coli.

Keywords: cell wall, alanine racemase, D-amino acids

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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