title: (1-Amino-2-propenyl) phosphonic acid, an inhibitor of alanine racemase and D-alanine:D-alanine ligase.
abstract: DL-(1-Amino-2-propenyl)phosphonic acid was synthesized through the sequential oxidation, sulfoxide elimination, and deprotection of diphenyl [1-[(benzyloxycarbonyl)amino]-3-(phenylthio)propyl] phosphonate. This analogue of vinylglycine is a strong inhibitor of the alanine racemases from Pseudomonas aeruginosa and Streptococcus faecalis and of the D-Ala:D-Ala ligase from this latter species. This molecule is ineffective against the whole bacterial cells. Unlike vinylglycine, this unsaturated phosphonate does not inhibit the following mammalian enzymes: aspartate aminotransferase, alanine aminotransferase, D-amino acid oxidase, which indicates its specificity. Thus, its incorporation in a peptide structure could induce interesting antimicrobial properties.
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*; D000410:Alanine Transaminase / Q000037:antagonists & inhibitors; D000591:Amino Acid Isomerases / Q000037:antagonists & inhibitors*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001219:Aspartate Aminotransferases / Q000037:antagonists & inhibitors; D001419:Bacteria / Q000187:drug effects; D003605:D-Amino-Acid Oxidase / Q000037:antagonists & inhibitors; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000494:pharmacology*; D010453:Peptide Synthases / Q000037:antagonists & inhibitors; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D009943:Organophosphorus Compounds; C048265:(1-amino-2-propenyl)phosphonic acid; D003605:D-Amino-Acid Oxidase; D001219:Aspartate Aminotransferases; D000410:Alanine Transaminase; D000591:Amino Acid Isomerases; D000411:Alanine Racemase; D010453:Peptide Synthases; C019638:D-alanylalanine synthetase