Synthesis of alpha-D-Galp-(1→3)-beta-D-Galf-(1→3)-D-Man, a terminal trisaccharide of Leishmania type-2 glycoinositolphospholipids

LUCÍA GANDOLFI DONADÍO; CAROLA GALLO -RODRIGUEZ; ROSA M. DE LEDERKREMER

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Lugar: Washington; Año: 2002 vol. 67 p. 4430 - 4435

0022-3263

The synthesis of R-D-Galp-(1f3)-â-D-Galf-(1f3)-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 â-D-Galf-(1-3)-D-Man unit, also present in the lipopeptidophosphoglycan of Trypanosoma cruzi, is reported.