Phosphinic acid inhibitors of D-alanyl-D-alanine ligase.

  title={Phosphinic acid inhibitors of D-alanyl-D-alanine ligase.},
  author={William H. Parsons and Arthur A. Patchett and Herbert G. Bull and William R Schoen and Dennis Taub and Jeannette Davidson and P L Combs and James P. Springer and H. H. Gadebusch and B A Weissberger},
  journal={Journal of medicinal chemistry},
  volume={31 9},
We report the synthesis of a series of phosphinic acid dipeptide analogues, NH2CH(R1)PO(OH)CH2CH(R2)CO2H, related to DAla-DAla. The best of these compounds are potent, essentially irreversible inhibitors of DAla-DAla ligase, and their preferred stereochemistry was shown by chiral synthesis of (1(S)-aminoethyl)(2(R)-carboxy-1-n-propyl)phosphinic acid, 12b, and by X-ray crystallography of its derivative benzyl [1(S)-[(benzyloxycarbonyl)-amino]ethyl](2(R)-carbomethoxy-1-propyl) phosphinate, 13, to… CONTINUE READING

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