Calixarene-iminosugar derivatives bearing four 1-deoxynojirimycin units at the upper or lower rim of calix[4]arenes in a fixed cone conformation were synthesized by copper-catalyzed azide-alkyne cycloaddition (CuAAC) and their inhibitory activity was evaluated against five glycosidases. Modest but significant affinity enhancements of up to seven per 1-deoxynojirimycin unit over the monovalent iminosugar derivative were observed for the inhibition of Jack bean (Canavalia ensiformis) a-mannosidase. It was also demonstrated that the residual copper ions did not contribute to the inhibitory properties of the newly prepared calixarene-based multivalent iminosugars.

Marra, A., Zelli, R., D'Orazio, G., LA FERLA, B., Dondoni, A. (2014). Synthesis and glycosidase inhibition properties of triazole-linked calixarene iminosugar clusters. TETRAHEDRON, 70(49), 9387-9393 [10.1016/j.tet.2014.10.035].

Synthesis and glycosidase inhibition properties of triazole-linked calixarene iminosugar clusters

D'ORAZIO, GIUSEPPE;LA FERLA, BARBARA;
2014

Abstract

Calixarene-iminosugar derivatives bearing four 1-deoxynojirimycin units at the upper or lower rim of calix[4]arenes in a fixed cone conformation were synthesized by copper-catalyzed azide-alkyne cycloaddition (CuAAC) and their inhibitory activity was evaluated against five glycosidases. Modest but significant affinity enhancements of up to seven per 1-deoxynojirimycin unit over the monovalent iminosugar derivative were observed for the inhibition of Jack bean (Canavalia ensiformis) a-mannosidase. It was also demonstrated that the residual copper ions did not contribute to the inhibitory properties of the newly prepared calixarene-based multivalent iminosugars.
Articolo in rivista - Articolo scientifico
Calix[4]arenes, Clusters, 1-Deoxynojirimycin derivatives, Glycosidases inhibitors, Iminosugars
English
2014
70
49
9387
9393
none
Marra, A., Zelli, R., D'Orazio, G., LA FERLA, B., Dondoni, A. (2014). Synthesis and glycosidase inhibition properties of triazole-linked calixarene iminosugar clusters. TETRAHEDRON, 70(49), 9387-9393 [10.1016/j.tet.2014.10.035].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/53784
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