AuBr(3) mediated glycosidations: synthesis of tetrasaccharide motif of the Leishmania donovani lipophosphoglycan.
Tetrasaccharide cap present in lipophosphoglycan of the Leishmania donovani responsible for visceral Leishmaniaisis is synthesized as a fully protected propargyl glycoside. AuBr(3) mediated selective glycosylation of propargyl 1,2-orthoester in the presence of propargyl glycoside is employed as a key step to obtain propargyl containing oligomers. Further, propargyl tetrasaccharide is connected with a long chain hydrocarbon containing azidothiol functionality situated at two terminal ends via 'click' reaction.
Department of Chemistry, Indian Insititute of Science Education & Research, Pune, 411 008, India.
Gopalsamy
G
Sureshkumar
Srinivas
S
Hotha
D006027:Glycosides / Q000737:chemistry*; D006028:Glycosphingolipids / Q000737:chemistry*; D006031:Glycosylation; D017612:Gold Compounds / Q000737:chemistry*; D007893:Leishmania donovani / Q000737:chemistry / Q000378:metabolism*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*
D006027:Glycosides; D006028:Glycosphingolipids; D017612:Gold Compounds; D009844:Oligosaccharides; C008290:lipophosphonoglycan