Synthesis of tartaric acid analogues of FR258900 and their evaluation as glycogen phosphorylase inhibitors

Gergely Varga, Tibor Docsa, Pál Gergely, László Juhász, László Somsák

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Di-O-cinnamoylated, -p-coumaroylated, and -feruloylated d-, l- and meso-tartaric acids were synthesized as analogues of the natural product FR258900, a glycogen phosphorylase (GP) inhibitor with in vivo antihyperglycaemic activity. The new compounds inhibited rabbit muscle GP in the low micromolar range, and bound to the allosteric site of the enzyme. The best inhibitor was 2,3-di-O-feruloyl meso-tartaric acid and had Ki values of 2.0 μM against AMP (competitive) and 3.36 μM against glucose-1-phosphate (non-competitive).

Original languageEnglish
Pages (from-to)1789-1792
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume23
Issue number6
DOIs
Publication statusPublished - Mar 15 2013

Keywords

  • Diabetes
  • FR258900
  • Glycogen phosphorylase
  • Inhibitor
  • Tartaric acid derivatives

ASJC Scopus subject areas

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

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