Abstract
The synthesis of trisaccharides 1 and 2, which contain the α-D-galactopyranosyl-(1→3)-β-Dgalactopyranosyl (α-Gal) motif, is described. A key step in the synthesis of the trisaccharides was the glycosylation of a monosaccharide acceptor with a disaccharide trichloroacetimidate donor. Subsequent modification of the products of this [2+1] glycosylation afforded 1 and 2, which contain an activated ester moiety suitable for reaction with, for example, proteins or amine-coated surfaces.
Highlights
The α-galactopyranosyl-(1→3)-β-D-galactopyranosyl disaccharide motif, known as the αGal antigen, is found commonly on the surface of mammalian tissues with the exception of old world monkeys and humans.[1]
Analysis of α-Gal response in Galactosyltransferase knockout (GTKO) mice is considered a good approximation for the study of accommodation and immune tolerance induction in transplantation of ABO-incompatible organs in humans,[18] as the α-Gal epitope is found in the A and B blood groups.[19]
Schmidt and coworkers described the synthesis of a related pentasaccharide using a convergent approach and trichloroacetimidate donors.[27]
Summary
The α-galactopyranosyl-(1→3)-β-D-galactopyranosyl disaccharide motif, known as the αGal antigen, is found commonly on the surface of mammalian tissues with the exception of old world monkeys and humans.[1]. This was achieved by reaction of each compound with sodium metal in THF/CH3OH, conditions that allowed the removal of the benzyl groups while leaving the alkene functionality intact. We report an efficient route to α-Gal trisaccharides 1 and 2 via a route in which a key transformation is the reaction of a disaccharide trichloroacetimidate donor with a monosaccharide acceptor.
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