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  • Title: Synthesis of the first stable phosphonamide transition state analogue.
    Author: de Medina P, Ingrassia LS, Mulliez ME.
    Journal: J Org Chem; 2003 Oct 31; 68(22):8424-30. PubMed ID: 14575467.
    Abstract:
    Three methods were selected for the one-pot synthesis of the fully protected beta-fluoroaminophosphonic acids, using the readily accessible N-protected beta-fluoroaminals. These were activated by acylation leading, by beta-elimination, to a transient N-acylimine immediately trapped by reactive forms of dialkyl phosphites. Avoiding basic conditions, the complete or partial deprotection of these N-protected beta-fluoroaminophosphonic esters allowed the synthesis of the free amino acids, their esters, and a racemic beta-trifluorophosphonamidic acid. The latter, which represents a transition state analogue formed by the bacterial transpeptidase, is perfectly stable at pH 4.7, contrary to the nonfluorinated compounds.
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