title: (beta-Chloro-alpha-aminoethyl)phosphonic acids as inhibitors of alanine racemase and D-alanine:D-alanine ligase.
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.
authors.forename: Y
authors.initials: Y
authors.lastname: Vo-Quang
authors.forename: D
authors.initials: D
authors.lastname: Carniato
authors.forename: L
authors.initials: L
authors.lastname: Vo-Quang
authors.forename: A M
authors.initials: AM
authors.lastname: Lacoste
authors.forename: E
authors.initials: E
authors.lastname: Neuzil
authors.forename: F
authors.initials: F
authors.lastname: Le Goffic
mesh_terms: D000411:Alanine Racemase / Q000037:antagonists & inhibitors*; D000591:Amino Acid Isomerases / Q000037:antagonists & inhibitors*; D000615:Aminoethylphosphonic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology*; D001667:Binding, Competitive; D055598:Chemical Phenomena; D002621:Chemistry; D013293:Enterococcus faecalis / Q000201:enzymology*; D009943:Organophosphorus Compounds / Q000494:pharmacology*; D010453:Peptide Synthases / Q000037:antagonists & inhibitors*; D011550:Pseudomonas aeruginosa / Q000201:enzymology*; D013329:Structure-Activity Relationship
chemical_list: D009943:Organophosphorus Compounds; D000615:Aminoethylphosphonic Acid; D000591:Amino Acid Isomerases; D000411:Alanine Racemase; D010453:Peptide Synthases; C019638:D-alanylalanine synthetase