Synthesis of galactofuranosyl-containing oligosaccharides corresponding to the glycosylinositolphospholipid of Trypanosoma cruzi.
The oligosaccharide beta-D-Galf-(1-->3)-alpha-D-Manp-(1-->2)-[beta-D-Galf- (1-->3)]-alpha-D-Manp-(1-->2)-alpha-D-Manp corresponds to the terminal end of the glycosylinositolphospholipid oligosaccharide of the protozoan Trypanosoma cruzi, the causative agent of Chagas' disease. Syntheses of methyl or ethylthio glycosides of the terminal disaccharide, trisaccharide, tetrasaccharide, and pentasaccharide corresponding to this structure are described. These syntheses employ the selective activation of a phenyl 1-selenogalactofuranoside or a phenyl 1-selenomannopyranoside donor over ethyl 1-thioglycoside acceptors with NIS-TfOH.
Randell
K D
KD
Department of Chemistry and Biochemistry, Simon Fraser University, Burnaby, B.C., Canada.
Johnston
B D
BD
Brown
P N
PN
Pinto
B M
BM
D000818:Animals; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis; D005690:Galactose / Q000737:chemistry*; D008969:Molecular Sequence Data; D010743:Phospholipids / Q000138:chemical synthesis*; D011134:Polysaccharides / Q000138:chemical synthesis; D014312:Trisaccharides / Q000138:chemical synthesis; D014349:Trypanosoma cruzi / Q000737:chemistry*
D004187:Disaccharides; D010743:Phospholipids; D011134:Polysaccharides; D014312:Trisaccharides; D005690:Galactose