Synthesis of O- and C-glycosides derived from β-(1,3)-D-glucans

Carbohydr Res. 2013 Dec 15:382:9-18. doi: 10.1016/j.carres.2013.07.007. Epub 2013 Jul 30.

Abstract

A series of β-(1,3)-d-glucans have been synthesized incorporating structural variations specifically on the reducing end of the oligomers. Both O- and C-glucosides derived from di- and trisaccharides have been obtained in good overall yields and with complete selectivity. Whereas the O-glycosides were obtained via a classical Koenigs-Knorr glycosylation, the corresponding C-glycosides were obtained through allylation of the anomeric carbon and further cross-metathesis reaction. Finally, the compounds were evaluated against two glycosidases and two endo-glucanases and no inhibitory activity was observed.

Keywords: Fungal infections; Glucans; Laminarans; Laminaribiose; Laminaritriose.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Sequence
  • Cellulase / antagonists & inhibitors
  • Chemistry Techniques, Synthetic
  • Clostridium thermocellum / enzymology
  • Disaccharides / chemistry
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Glucans / chemistry*
  • Glycoside Hydrolases / antagonists & inhibitors
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Glycosides / pharmacology*
  • Glycosylation
  • Hordeum / enzymology
  • Hydrophobic and Hydrophilic Interactions
  • Molecular Sequence Data
  • Monosaccharides / chemical synthesis*
  • Monosaccharides / chemistry
  • Polysaccharides / chemistry
  • Structure-Activity Relationship
  • Trisaccharides / chemistry

Substances

  • C-glycoside
  • Disaccharides
  • Enzyme Inhibitors
  • Glucans
  • Glycosides
  • Monosaccharides
  • Polysaccharides
  • Trisaccharides
  • laminaribiose
  • laminaran
  • Glycoside Hydrolases
  • Cellulase