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Fluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols

TitleFluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols
Publication TypeJournal Article
Year of Publication2006
AuthorsGreimel, P, Hausler, H, Lundt, I, RUPITZ, K, Stutz, AE, Tarling, CA, Withers, SG, Wrodnigg, TM
JournalBIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume16
Pagination2067-2070
Date PublishedAPR 15
ISSN0960-894X
Abstract

1,5-Dideoxy-1,5-iminoalditols of various configurations as well as isofagomine were N-alkylated with non-polar straight chain spacer-arms by a set of simple standard procedures. The spacer-arms' terminal functional groups, primary amines, were employed to introduce fluorescent tags such as dansyl and dapoxyl moieties. Resulting derivatives in the D-xylo, D-gluco, D-galacto as well as GlcNAc series showed distinctly improved glycosidase inhibitory activities compared to parent compounds and are designed to be useful analytical tools. (C) 2006 Elsevier Ltd. All rights reserved.

DOI10.1016/j.bmcl.2006.01.095