Synthesis of 1,2,3-triazole-linked galactohybrids and their inhibitory activities on galectins
(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-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... (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-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. (Less)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/4800418
- author
- Mackeviča, Jevgeņija ; Ostrovskis, Pāvels ; Leffler, Hakon LU ; Nilsson, Ulf LU ; Rudovica, Vita ; Viksna, Arturs ; Belyakov, Sergey and Turksa, Māris
- organization
- publishing date
- 2014
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- 1,2,3-triazoles, Click chemistry, Extended bis-triazolyl linker, Galactose derivatives, Galectins, Residual copper content
- in
- Arkivoc
- volume
- 2014
- issue
- 3
- pages
- 23 pages
- 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
- 2016-04-01 11:16:27
- date last changed
- 2023-02-08 10:01:01
@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-<i>O</i>-isopropylidene-α-D-galactofuranose <i>via </i>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 Na<sub>2</sub>S 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<sub>d</sub> 50 μM. One of the obtained disaccharides was characterized by X-ray analysis.}}, author = {{Mackeviča, Jevgeņija and Ostrovskis, Pāvels and Leffler, Hakon and Nilsson, Ulf and Rudovica, Vita and Viksna, Arturs and Belyakov, Sergey and Turksa, Māris}}, issn = {{1551-7012}}, keywords = {{1,2,3-triazoles; Click chemistry; Extended bis-triazolyl linker; Galactose derivatives; Galectins; Residual copper content}}, 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 = {{https://lup.lub.lu.se/search/files/2524572/7583389}}, doi = {{10.3998/ark.5550190.p008.402}}, volume = {{2014}}, year = {{2014}}, }