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Synthesis of 1,2,3-triazole-linked galactohybrids and their inhibitory activities on galectins

På svenska

Author

  • Jevgeņija Mackeviča
  • Pāvels Ostrovskis
  • Hakon Leffler
  • Ulf Nilsson
  • Vita Rudovica
  • Arturs Viksna
  • Sergey Belyakov
  • Māris Turksa

Summary, in English

Here a synthesis of novel galactose-1,2,3-triazole conjugates is described. The title compounds were obtained from 3-azido-3-deoxy-1,2: 5,6-di-O-isopropylidene-α-D-galactofuranose via a copper catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction. It was demonstrated that the title compounds in their isopropylidene-protected form tend to chelate copper. The copper content can be diminished to 10 ppm by successive treatment with EDTA and Na2S followed by chromatographic purification. Acidic hydrolysis of the acetonide protecting groups provided water soluble galactohybrids that were tested for their affinity towards galectin-1 and galectin-3. The trimeric galactohybrid exhibited a 160-fold preference for galectin-3 binding with Kd 50 μM. One of the obtained disaccharides was characterized by X-ray analysis.

Publishing year

2014

Language

English

Pages

90-112

Publication/Series

Arkivoc

Volume

2014

Issue

3

Document type

Journal article

Publisher

Arkat USA Inc

Topic

  • Microbiology in the medical area
  • Immunology in the medical area

Keywords

  • 1,2,3-triazoles
  • Click chemistry
  • Extended bis-triazolyl linker
  • Galactose derivatives
  • Galectins
  • Residual copper content

Status

Published

ISBN/ISSN/Other

  • ISSN: 1551-7012