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.
Glycogroup, Institut für Organische Chemie, Technische Universität Graz, Stremayrgasse 16, A-8010 Graz, Austria.
Peter
P
Greimel
Herwig
H
Häusler
Inge
I
Lundt
Karen
K
Rupitz
Arnold E
AE
Stütz
Chris A
CA
Tarling
Stephen G
SG
Withers
Tanja M
TM
Wrodnigg
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