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

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Abstract

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-alpha-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 K-d 50 mu M. One of the obtained disaccharides was characterized by X-ray analysis.

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Subject classification (UKÄ) – MANDATORY

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

Keywords

  • click chemistry, extended bis-triazolyl linker, Galactose derivatives, 3-triazoles, 2, 1, residual copper content, galectins
Original languageEnglish
Pages (from-to)90-112
JournalArkivoc
Volume2014
Issue number3
Publication statusPublished - 2014
Publication categoryResearch
Peer-reviewedYes

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