NEW SOLID-PHASE OLIGOSACCHARIDE SYNTHESIS ON GLYCOPEPTIDES BOUND TO ASOLID-PHASE

Citation
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
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
0300922X
Issue
3
Year of publication
1997
Pages
281 - 293
Database
ISI
SICI code
0300-922X(1997):3<281:NSOSOG>2.0.ZU;2-K
Abstract
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.