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

Bioorganic & Medicinal Chemistry Letters
2006.0

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.

Knowledge Graph

Similar Paper

Fluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols
Bioorganic & Medicinal Chemistry Letters 2006.0
Powerful probes for glycosidases
Bioorganic & Medicinal Chemistry Letters 2001.0
Novel, lipophilic derivatives of 2,5-dideoxy-2,5-imino-d-mannitol (DMDP) are powerful β-glucosidase inhibitors
Bioorganic & Medicinal Chemistry Letters 2001.0
Flexible synthesis and biological evaluation of novel 5-deoxyadenophorine analogues
Bioorganic & Medicinal Chemistry Letters 2006.0
γ-Hydroxyethyl piperidine iminosugar and N-alkylated derivatives: A study of their activity as glycosidase inhibitors and as immunosuppressive agents
Bioorganic & Medicinal Chemistry 2014.0
α-1-C-Alkyl-1-deoxynojirimycin derivatives as potent and selective inhibitors of intestinal isomaltase: remarkable effect of the alkyl chain length on glycosidase inhibitory profile
Bioorganic & Medicinal Chemistry Letters 2004.0
Synthesis and glycosidase inhibition of 5-C-alkyl-DNJ and 5-C-alkyl-l-ido-DNJ derivatives
European Journal of Medicinal Chemistry 2021.0
Synthesis and characterization of novel, conjugated, fluorescent DNJ derivatives for α-glucosidase recognition
Bioorganic & Medicinal Chemistry 2017.0
Design, synthesis and glycosidase inhibition of C-4 branched LAB and DAB derivatives
European Journal of Medicinal Chemistry 2022.0
Five-membered iminocyclitol α-glucosidase inhibitors: Synthetic, biological screening and in silico studies
Bioorganic & Medicinal Chemistry 2013.0