Epoxide derivatives of pipecolic acid and proline are inhibitors of pipecolate oxidase

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Abstract

The cis-4,5-epoxide derivative of L-pipecolic acid (2S,4S,5R-epoxypipecolic acid, cis-3) was synthesized and found to serve as an excellent substrate for L-pipecolate oxidase (L-PO) and also to cause time-dependent, irreversible inactivation of the enzyme. Data are presented showing this compound is a mechanism-based inhibitor of L-PO, whereas 2S,3R,4S-epoxyproline acts as a reversible inhibitor.

Original languageEnglish (US)
Pages (from-to)739-744
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume8
Issue number7
DOIs
StatePublished - Apr 7 1998

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ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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