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

In English

Författare

  • 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.

Publiceringsår

2014

Språk

Engelska

Sidor

90-112

Publikation/Tidskrift/Serie

Arkivoc

Volym

2014

Issue

3

Dokumenttyp

Artikel i tidskrift

Förlag

Arkat USA Inc

Ämne

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

Nyckelord

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

Status

Published

ISBN/ISSN/Övrigt

  • ISSN: 1551-7012