Enantiospecificity of glutamate carboxypeptidase II inhibition.

  title={Enantiospecificity of glutamate carboxypeptidase II inhibition.},
  author={T. Tsukamoto and P. Majer and D. Vitharana and C. Ni and Bunda Hin and X. Lu and Ajit G. Thomas and K. Wozniak and D. Calvin and Y. Wu and B. Slusher and D. Scarpetti and G. Bonneville},
  journal={Journal of medicinal chemistry},
  volume={48 7},
Two representative glutamate carboxypeptidase II (GCP II) inhibitors, 2-(hydroxypentafluorophenylmethyl-phosphinoylmethyl)pentanedioic acid 2 and 2-(3-mercaptopropyl)pentanedioic acid 3, were synthesized in high optical purities (>97%ee). The two enantiomers of 2 were prepared from previously reported chiral intermediates, (R)- and (S)-2-(hydroxyphosphinoylmethyl)pentanedioic acid benzyl esters 8. The synthesis of (R)- and (S)-3 involves the hydrolysis of (R)- and (S)-3-(2-oxo-tetrahydro… Expand
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