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. (Less)
Highlights
Carbohydrate-protein interactions play many important roles in biochemical processes
The key starting material, 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-galactofuranose (2), was obtained in few straightforward steps[23] from diacetone-D-glucose derived ketone 1, which is available on a hundred gram scale.[24]
We have developed a straightforward synthesis of novel divalent and multivalent galactopyranose hybrids
Summary
Carbohydrate-protein interactions play many important roles in biochemical processes These include lectin-carbohydrate recognition[1,2,3] and processes catalyzed by glycosidases,[4,5,6] glycosyltransferases[7] and glycogen phosphorylases.[8] Very often modified carbohydrates are used to investigate these processes[9,10] and to create suitable inhibitors of the aforementioned enzymes. We aimed to develop a user-friendly synthesis of novel C(3)-modified galactohybrids and to determine their affinities towards galectin-1 and galectin-3
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