Fluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols.
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.
Greimel
Peter
P
Glycogroup, Institut für Organische Chemie, Technische Universität Graz, Stremayrgasse 16, A-8010 Graz, Austria.
Häusler
Herwig
H
Lundt
Inge
I
Rupitz
Karen
K
Stütz
Arnold E
AE
Tarling
Chris A
CA
Withers
Stephen G
SG
Wrodnigg
Tanja M
TM
D000478:Alkylation; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D005959:Glucosidases / Q000037:antagonists & inhibitors*; D050112:Imino Pyranoses / Q000138:chemical synthesis; D008956:Models, Chemical; D010880:Piperidines / Q000138:chemical synthesis; D013402:Sugar Alcohols / Q000138:chemical synthesis
D004791:Enzyme Inhibitors; D005456:Fluorescent Dyes; D050112:Imino Pyranoses; D010880:Piperidines; D013402:Sugar Alcohols; C098432:isofagomine; D005959:Glucosidases