Synthesis of 1,2,3-triazole-linked galactohybrids and their inhibitory activities on galectins
| العنوان: | Synthesis of 1,2,3-triazole-linked galactohybrids and their inhibitory activities on galectins |
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| المؤلفون: | Mackeviča, Jevgeņija, Ostrovskis, Pāvels, Leffler, Hakon, Nilsson, Ulf, Rudovica, Vita, Viksna, Arturs, Belyakov, Sergey, Turksa, Māris |
| المصدر: | Arkivoc. 2014(3):90-112 |
| مصطلحات موضوعية: | 3-triazoles, Click chemistry, Extended bis-triazolyl linker, Galactose derivatives, Galectins, Residual copper content, Medicin och hälsovetenskap, Medicinska och farmaceutiska grundvetenskaper, Mikrobiologi inom det medicinska området, Medical and Health Sciences, Basic Medicine, Microbiology in the medical area, Immunologi inom det medicinska området, Immunology in the medical area |
| الوصف: | 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. |
| وصف الملف: | electronic |
| URL الوصول: | https://lup.lub.lu.se/record/4800418 https://portal.research.lu.se/files/2524572/7583389 http://dx.doi.org/10.3998/ark.5550190.p008.402 |
| قاعدة البيانات: | SwePub |
| تدمد: | 15517012 |
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| DOI: | 10.3998/ark.5550190.p008.402 |