H. Paulsen et al., NEW SOLID-PHASE OLIGOSACCHARIDE SYNTHESIS ON GLYCOPEPTIDES BOUND TO ASOLID-PHASE, Journal of the Chemical Society. Perkin transactions. I, (3), 1997, pp. 281-293
A solid-phase oligosaccharide synthesis has been developed which utili
ses glycopeptides bound to the solid phase. The products are glycopept
ides elongated at the saccharide chain. The glycosyl accepters, which
are assembled by simple solid-phase glycopeptide synthesis, contain 2-
azido-2-deoxy-alpha-D-galactose with unsubstituted 3-OH or 6-OH groups
, which can be glycosylated. Suitable glycosyl donors are perbenzoylat
ed trichloroacetimidates of D-galactose or 2-amino-2-deoxy-D-glucose,
although the 2-amino group must be protected with Teoc. A correspondin
g additional saccharide unit is added with a beta-glycosidic linkage.
With disaccharide donors, glycopeptides with linear trisaccharide side
chains are obtained. By performing the solid-phase glycosylation synt
hesis twice in succession glycopeptides with branched trisaccharide ch
ains have been obtained.