Synthesis of N-(β-d-glucopyranosyl) monoamides of dicarboxylic acids as potential inhibitors of glycogen phosphorylase

K. Czifrák, Zsuzsa Hadady, T. Docsa, P. Gergely, Jürgen Schmidt, Ludger Wessjohann, L. Somsák

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

O-Peracetylated N-(β-d-glucopyranosyl)imino trimethylphosphorane obtained in situ from 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl azide and PMe3 was reacted with saturated and unsaturated aliphatic and aromatic dicarboxylic acids, or their anhydrides, or monoesters to give the corresponding N-(β-d-glucopyranosyl) monoamides of dicarboxylic acids or derivatives. The acetyl protecting groups were removed according to the Zemplén protocol to give a series of compounds which showed moderate inhibitory effects against rabbit muscle glycogen phosphorylase b. The best inhibitor was 3-(N-β-d-glucopyranosyl-carbamoyl)propanoic acid (7) with Ki = 20 μM.

Original languageEnglish
Pages (from-to)947-956
Number of pages10
JournalCarbohydrate Research
Volume341
Issue number8
DOIs
Publication statusPublished - Jun 12 2006

Fingerprint

Glycogen Phosphorylase
Dicarboxylic Acids
Phosphorylase b
Azides
Anhydrides
Carboxylic acids
Muscle
Rabbits
Derivatives
Muscles
propionic acid

Keywords

  • Glucose analogues
  • Glycogen phosphorylase
  • Inhibitors
  • N-Glycosylamides

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthesis of N-(β-d-glucopyranosyl) monoamides of dicarboxylic acids as potential inhibitors of glycogen phosphorylase. / Czifrák, K.; Hadady, Zsuzsa; Docsa, T.; Gergely, P.; Schmidt, Jürgen; Wessjohann, Ludger; Somsák, L.

In: Carbohydrate Research, Vol. 341, No. 8, 12.06.2006, p. 947-956.

Research output: Contribution to journalArticle

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AU - Hadady, Zsuzsa

AU - Docsa, T.

AU - Gergely, P.

AU - Schmidt, Jürgen

AU - Wessjohann, Ludger

AU - Somsák, L.

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KW - Glucose analogues

KW - Glycogen phosphorylase

KW - Inhibitors

KW - N-Glycosylamides

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