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Synthesis of Novel 3-Deoxy-3-C-Triazolylmethyl-Allose Derivatives and Evaluation of Their Biological Activity

By Jekaterina Rjabova, Vitālijs Rjabovs, Antonio José Moreno Vargas, Elena Moreno Clavijo and Māris Turks


Recently, monosaccharide-triazole conjugates have proved to possess a large variety of useful biological activities. This paper describes synthesis of a new series of 3-deoxy-3-C-triazolylmethyl-allose derivatives. These latter are obtained from acetonide-protected 3-deoxy-3-azidomethyl allose and commercial alkynes via Cu(I) catalyzed 1,3-dipolar cycloaddition. The obtained molecular scaffolds differ from those described earlier by methylene linker (-CH2-) between the C(3) of allose and triazole moiety. It was demonstrated that acetonide-protected monosaccharide, 3-deoxy-3-C-(4-phenyl-1H-1,2,3-triazol-1-yl)methyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose, inhibited α-L-fucosidase for 26% at 0.1 mM concentration, but a deprotected analog, 3-deoxy-3-C-(4-(4-tert-butylphenyl)-1H-1,2,3-triazol-1-yl)methyl-β-D-allofuranose, showed 15% inhibition of β-glucosidase at 1 mM concentration

Topics: 3-deoxy-3-C-triazolylmethyl-allose; methylene linker; triazolyl-monosaccharides; click chemistry, inhibitors of glycosidases
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