Use of a phenyl 1-selenogalactofuranoside as a glycosyl donor for the synthesis of galactofuranosyl-containing disaccharides.
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.
Johnston
B D
BD
Department of Chemistry, Simon Fraser University, Burnaby, B.C., Canada.
Pinto
B M
BM
D000818:Animals; D000953:Antigens, Protozoan / Q000737:chemistry*; D004187:Disaccharides / Q000138:chemical synthesis*; D005690:Galactose / Q000737:chemistry; D016566:Organoselenium Compounds / Q000737:chemistry; D010457:Peptidoglycan / Q000737:chemistry*; D010743:Phospholipids / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry; D014349:Trypanosoma cruzi / Q000737:chemistry*
D000953:Antigens, Protozoan; D004187:Disaccharides; D016566:Organoselenium Compounds; D010457:Peptidoglycan; D010743:Phospholipids; D013865:Thioglycosides; C014643:lipopeptidophosphoglycan; C112227:phenyl 1-selenogalactofuranoside; D005690:Galactose