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

Bioorg Med Chem Lett. 2006 Apr 15;16(8):2067-70. doi: 10.1016/j.bmcl.2006.01.095. Epub 2006 Feb 14.

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.

Publication types

  • Comparative Study

MeSH terms

  • Alkylation
  • Enzyme Inhibitors / chemical synthesis*
  • Fluorescent Dyes / chemical synthesis*
  • Glucosidases / antagonists & inhibitors*
  • Imino Pyranoses / chemical synthesis
  • Models, Chemical
  • Piperidines / chemical synthesis
  • Sugar Alcohols / chemical synthesis

Substances

  • Enzyme Inhibitors
  • Fluorescent Dyes
  • Imino Pyranoses
  • Piperidines
  • Sugar Alcohols
  • isofagomine
  • Glucosidases