Design, synthesis, and binding studies of bidentate Zn-chelating peptidic inhibitors of glyoxalase-I

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Abstract

The known affinity of ethyl acetoacetate (ACC) toward divalent zinc prompted us to attempt its employment as a chelating moiety in the design of glyoxalase-I inhibitors. A practical synthetic route was developed to incorporate this pharmacophore into the side chain of glutamic acid, with flexibility to allow incorporation of additional functionality at the end-stage of the synthesis. Herein, the details of this synthetic approach as well as the evaluation of the resultant β-keto ester compounds are reported.

Original languageEnglish (US)
Pages (from-to)3793-3797
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume17
Issue number13
DOIs
StatePublished - Jul 1 2007

Keywords

  • Ethyl acetoacetate
  • Glutathione
  • Glyoxalase
  • Methylglyoxal
  • Transition-state inhibitor
  • β-Keto ester

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