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 cyclo-addition (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) alpha-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. (C) 2014 Elsevier Ltd. All rights reserved.
Synthesis and glycosidase inhibition properties of triazole-linked calixarene–iminosugar clusters / Marra, Alberto; Zelli, Renaud; D'Orazio, Giuseppe; La Ferla, Barbara; Dondoni, Alessandro. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 70:49(2014), pp. 9387-9393. [10.1016/j.tet.2014.10.035]
Synthesis and glycosidase inhibition properties of triazole-linked calixarene–iminosugar clusters
D'Orazio, Giuseppe;
2014-01-01
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 cyclo-addition (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) alpha-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. (C) 2014 Elsevier Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
