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.
MeSH terms
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Alanine Racemase / antagonists & inhibitors*
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Alanine Transaminase / antagonists & inhibitors
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Amino Acid Isomerases / antagonists & inhibitors*
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Anti-Bacterial Agents / chemical synthesis
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Anti-Bacterial Agents / pharmacology*
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Aspartate Aminotransferases / antagonists & inhibitors
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Bacteria / drug effects
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D-Amino-Acid Oxidase / antagonists & inhibitors
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Organophosphorus Compounds / chemical synthesis
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Organophosphorus Compounds / pharmacology*
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Peptide Synthases / antagonists & inhibitors
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Structure-Activity Relationship
Substances
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Anti-Bacterial Agents
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Organophosphorus Compounds
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(1-amino-2-propenyl)phosphonic acid
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D-Amino-Acid Oxidase
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Aspartate Aminotransferases
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Alanine Transaminase
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Amino Acid Isomerases
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Alanine Racemase
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Peptide Synthases
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D-alanylalanine synthetase