Synthesis and Evaluation of Lipophilic Aza??C??glycosides as Inhibitors of Glucosylceramide Metabolism

…, WE Donker??Koopman, B Kuijper…

Index: Wennekes, Tom; Van Den Berg, Richard J. B. H. N.; Boltje, Thomas J.; Donker-Koopman, Wilma E.; Kuijper, Bastiaan; Van Der Marel, Gijsbert A.; Strijland, Anneke; Verhagen, Carlo P.; Aerts, Johannes M. F. G.; Overkleeft, Herman S. European Journal of Organic Chemistry, 2010 , # 7 p. 1258 - 1283

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Citation Number: 11

Abstract

Abstract The structure–activity relationship of lipophilic aza-C-glycosides as inhibitors of the three enzymes of glucosylceramide metabolism is investigated. A library of β-aza-C- glycosides was synthesized with variations in N-alkylation and the linker length/type to the lipophilic moiety. A cross-metathesis reaction was used to prepare a second library of α-aza- C-glycosides with D-gluco, L-ido and D-xylo iminosugar cores possessing analogous ...