Use of a phenyl 1-selenogalactofuranoside as a glycosyl donor for the synthesis of galactofuranosyl-containing disaccharides.

Abstract

The use of acetylated phenyl 1-seleno-beta-D-galactofuranoside as a glycosyl donor for the synthesis of protected D-Galf-beta-(1-->3)-alpha-D-Manp as its methyl or ethylthio glycoside has been demonstrated. Activation of the selenoglycoside over a thioglycoside acceptor by NIS/TfOH is extremely selective and gives the ethylthio disaccharide in 91% yield. The parent disaccharide is found as a terminal and branched unit in the lipopeptidophosphoglycan oligosaccharides of the protozoan Trypanosoma cruzi, the causative agent of Chagas' disease.

• Authors: B D Johnston, B M Pinto
• Journal: Carbohydrate research (Carbohydr Res) Vol. 305 Issue 2 Pg. 289-92 (Dec 1997) ISSN: 0008-6215 [Print] Netherlands
• PMID: 9581281 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antigens, Protozoan
• Disaccharides
• Organoselenium Compounds
• Peptidoglycan
• Phospholipids
• Thioglycosides
• lipopeptidophosphoglycan
• phenyl 1-selenogalactofuranoside
• Galactose

Topics

• Animals
• Antigens, Protozoan (chemistry)
• Disaccharides (chemical synthesis)
• Galactose (chemistry)
• Organoselenium Compounds (chemistry)
• Peptidoglycan (chemistry)
• Phospholipids (chemistry)
• Thioglycosides (chemistry)
• Trypanosoma cruzi (chemistry)