Synthesis of alpha-D-Galp-(1-->3)-beta-D-Galf-(1-->3)-D-man, a terminal trisaccharide of Leishmania type-2 glycoinositolphospholipids.
The synthesis of alpha-D-Galp-(1-->3)-beta-D-Galf-(1-->3)-D-Man, present in the type-2 glycoinositolphospholipids and in the core of the lipophosphoglycan of Leishmania, is described. The glycosyl aldonolactone approach, followed by reduction of the lactone with diisoamylborane, was utilized for the introduction of the internal galactofuranosyl unit and the trichloroacetimidate method for the O-glycosidation reaction. A high-yield synthesis of the beta-D-Galf-(1-3)-D-Man unit, also present in the lipopeptidophosphoglycan of Trypanosoma cruzi, is reported.
Gandolfi-Donadio
Lucia
L
CIHIDECAR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón II, 1428 Buenos Aires, Argentina.
Gallo-Rodriguez
Carola
C
de Lederkremer
Rosa M
RM
D000818:Animals; D002240:Carbohydrate Sequence; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D002855:Chromatography, Thin Layer; D006028:Glycosphingolipids / Q000378:metabolism; D007891:Leishmania / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D014349:Trypanosoma cruzi / Q000737:chemistry*
C469648:Galp-(1-3)-Galf-(1-3)-Man; D006028:Glycosphingolipids; D014312:Trisaccharides; C008290:lipophosphonoglycan