Glucose-Based AB2-Building Blocks for the Construction of Branched Glycopeptidomimetics

Abstract

Glycopeptido derivatives are attractive oligosaccharide mimetics which allow the use of peptide-coupling reactions for the assembly of carbohydrate units instead of the more difficult glycosylation procedures. Moreover, glycopeptidomimetics are attractive as synthetic ligands for carbohydrate-specific molecular recognition. With regard to the multiantennary nature of the naturally occurring N-glycans, we synthesized the orthogonally protected glucose-based AB2-building blocks 1 and 2, which allow the assembly of branched glycopeptidomimetics by peptide-coupling reactions. This was exemplified by the synthesis of multivalent glycopeptidomimetics 14 and 15 derived therefrom.