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

Mackevica, Jevgenija; Ostrovskis, Pavels; Leffler, Hakon LU ; Nilsson, Ulf LU ; Rudovica, Vita; Viksna, Arturs; Belyakov, Sergey and Turksa, Maris (2014) In Arkivoc 2014(3). p.90-112
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... (More)
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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
click chemistry, extended bis-triazolyl linker, Galactose derivatives, 3-triazoles, 2, 1, residual copper content, galectins
in
Arkivoc
volume
2014
issue
3
pages
90 - 112
publisher
Arkat USA Inc
external identifiers
  • wos:000343046700007
  • scopus:84894134202
ISSN
1551-7012
DOI
10.3998/ark.5550190.p008.402
language
English
LU publication?
yes
id
37bc3b62-a40b-4349-9faa-3f302828aeb0 (old id 4800418)
date added to LUP
2014-11-25 22:22:49
date last changed
2017-01-01 04:18:39
@article{37bc3b62-a40b-4349-9faa-3f302828aeb0,
  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.},
  author       = {Mackevica, Jevgenija and Ostrovskis, Pavels and Leffler, Hakon and Nilsson, Ulf and Rudovica, Vita and Viksna, Arturs and Belyakov, Sergey and Turksa, Maris},
  issn         = {1551-7012},
  keyword      = {click chemistry,extended bis-triazolyl linker,Galactose derivatives,3-triazoles,2,1,residual copper content,galectins},
  language     = {eng},
  number       = {3},
  pages        = {90--112},
  publisher    = {Arkat USA Inc},
  series       = {Arkivoc},
  title        = {Synthesis of 1,2,3-triazole-linked galactohybrids and their inhibitory activities on galectins},
  url          = {http://dx.doi.org/10.3998/ark.5550190.p008.402},
  volume       = {2014},
  year         = {2014},
}