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.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
